54 results about "Wittig reaction" patented technology

The present invention discloses a synthesis method of ursodeoxycholic acid by using the plant-derived compound BA as a raw material to synthesize ursodeoxycholic acid through the steps of ethylene glycol or neopentyl glycol protection, oxidation, Wittig reaction, deprotection, reduction and hydrolysis, etc. The raw materials used for the synthesis of ursodeoxycholic acid in the present invention are cheap and easy to get, the synthesis steps are easy to operate, the yield is high, the reaction is environmentally friendly, and the industrial production is convenient.

The application discloses a preparation method of beta-carotene, which comprises the following steps: 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl triphenyl phosphonium salt (C15 phosphonium salt) cis-trans isomer and 2,7-dimethyl-2,4,6-octatriene-1,8-dial (C10) are dissolved in a water and a water incompatible solvent system, and Wittig reaction is generated under the action of an alkali. The reaction system can avoid that by-product inorganic salt is wrapped in the product, and the content of inorganic salt impurities in the product is reduced. In addition, the proportion of C15 phosphonium salt cis-trans isomer is controlled, a C15 phosphonium salt hydrolysis side reaction is inhibited, and the reaction yield is improved.

The invention relates to the technical field of chemical synthesis, and particularly discloses a compound with a peculiar smell removing function as well as a preparation method and application thereof. The chemical name of the compound is 2-ethoxy-3-((E)-methoxy-3-oxopropyl-1-alkene-1-yl) phenyl cinnamate, the smell of the compound is extremely light, sulfur-containing and nitrogen-containing compounds causing stink can be captured through a Michael addition reaction, and efficient peculiar smell removal is achieved. The preparation method comprises the following steps: (1) taking cinnamic acid as an initial raw material, and reacting with diethylamino sulfur trifluoride to prepare cinnamic acid acyl fluoride; (2) carrying out an esterification reaction on the cinnamic acid acyl fluoride and 2-methoxy-3-hydroxybenzaldehyde in the presence of 4-dimethylaminopyridine, so as to obtain 2-methoxy-3-formyl phenyl cinnamate; and (3) carrying out Wittig reaction on the 2-methoxy-3-formyl phenyl cinnamate and a phosphorus ylide reagent, so as to obtain the target compound.

The invention discloses a preparation method of beta-carotene. The preparation method comprises the following steps: dissolving an aqueous solution of 3-methyl-5-(2, 6, 6-trimethyl-1-cyclohexene-1-yl)-2, 4-pentadienyl triphenylphosphine salt (C15 phosphine salt) and 2, 7-dimethyl-2, 4, 6-octtriene-1, 8-dialdehyde (C10) cis-trans isomer in a solvent, carrying out wittig reaction under the action of alkali, and carrying out isomerization to obtain the product. By controlling the proportion of C10 cis-trans isomers of the reaction system, the content of the C25 aldehyde intermediate can be reduced, and the reaction yield and the product quality can be improved.

The invention discloses THK01 and derivatives thereof, a preparation method and application of THK01 and derivatives thereof in preparation of anti-inflammatory drugs, and the THK01 and derivatives thereof are prepared by performing a series of chemical reactions on o-nitrobenzaldehyde containing a specific substituent group, including Wittig reaction, Diels-Alder reaction, Cadolan reaction, Fischer indole synthesis reaction, demethylation reaction, reduction reaction, click chemical reaction and the like. The THK01 structure modified derivatives with different substituent groups are obtained. The THK01 structure modified derivative disclosed by the invention is diversified in synthetic route and high in reaction success rate; in-vitro and in-vivo experiments show that the compounds can significantly inhibit NO generation and inflammatory response at low concentration, and can effectively treat inflammatory bowel disease and acute pneumonia induced by H1N1 virus in an animal model. These findings provide valuable candidate compounds and new treatment strategies for developing novel, safe and efficient anti-inflammatory drugs.

The invention relates to a synthetic method of chlorinated methyl styrene, which comprises the following steps: (1) in the presence of a reducing agent, carrying out selective reduction reaction on terephthalaldehyde or isophthalaldehyde to obtain p-hydroxymethylbenzaldehyde or 3-(hydroxymethyl) benzaldehyde; (2) in the presence of a chlorination reagent, carrying out chlorination reaction on the p-hydroxymethylbenzaldehyde or 3-(hydroxymethyl) benzaldehyde obtained in the step (1) to obtain p-chloromethylbenzaldehyde or 3-(chloromethyl) benzaldehyde; and (3) in the presence of alkali, carrying out Wittig reaction on the p-chloromethyl benzaldehyde or 3-(chloromethyl) benzaldehyde obtained in the step (2) to generate p-chloromethyl styrene or m-chloromethyl styrene. The method avoids the use of highly toxic chlorine or intermediates difficult to synthesize, has the advantages of short steps, mild conditions, high selectivity, high yield, environmental friendliness and the like, and has a good industrial application prospect.

This invention provides a method for preparing high-purity olaparib, belonging to the field of pharmaceutical synthesis technology. The method uses dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphate as the starting material, reacting it with compound 2 via a Wittig reaction to generate compound 3. Compound 3 reacts with hydrazine hydrate to generate compound 4. Compound 4 is hydrolyzed and acidified to give compound 5. Compound 5 reacts with thionyl chloride to give compound 6. Compound 6 is then condensed with compounds 7 and 9 to obtain olaparib. This invention uses readily available raw materials, is simple to operate and process, has mild reaction conditions, achieves a total yield of up to 90%, a purity >99%, is environmentally friendly, and is suitable for industrial production.

The present invention relates to a pyridine derivative-containing triarylethylene photochromic material and its preparation and application methods. A pyridine ring or its derivative containing a formaldehyde substituent at one end is subjected to a Corey-Funchs reaction to synthesize its dibromosubstituted product; then, the dibromosubstituted product is reacted with an aromatic compound or heterocyclic compound containing a boric acid or pinacol borate group through a Suzuki reaction; or a benzophenone derivative is reacted with a pyridine ring or its derivative containing a diethyl phosphate group through a Wittig reaction to obtain the pyridine derivative-containing triarylethylene photochromic material. The present invention has low-cost raw materials and a simple and easy synthesis process. The prepared photochromic material has the advantages of dual light / proton response, high color purity, a wide color change wavelength range, and long color change durability. This expands the original triarylethylene photochromic material with a single stimulus response to a light / proton dual-responsive photochromic material, and also expands the color change range from orange to red and purple. The material is suitable for multiple fields such as inspection, storage encryption, and biological imaging.

A method for the industrial production of teprenone and its application. The present invention belongs to the field of teprenone synthesis. The purpose of the present invention is to solve the technical problems of the existing teprenone synthesis method, which has a long route, many side reactions, and requires the use of special reagents. The method of the present invention comprises the following steps: first, farnesene is reacted with acetoacetate in the presence of a catalyst to obtain farnesene ketone ester, which is then decarboxylated to produce farnesene acetone, and then subjected to a reduction reaction, a halogenation reaction, and a Wittig reaction to obtain teprenone. The method avoids the shortcomings of existing processes, has fewer conversion steps in the synthesis route, and produces teprenone with high yield and purity, making it suitable for industrial production. The teprenone of the present invention is used as a drug for treating gastric diseases.

The invention relates to a preparation method of a cefditoren pivoxil intermediate. The preparation method comprises the following steps: step 1, adding GCLE, a bromine reagent and triphenylphosphine into an aprotic solvent for reaction to obtain a phosphorus ylide reagent; step 2, adding a mixed solvent and 4-methylthiazole-5-formaldehyde into the phosphorus ylide reagent, and carrying out Wittig reaction to obtain a cis-intermediate Z; 3, the cis-intermediate Z is added into phenol for a reaction; and adding immobilized penicillin acylase for reaction to obtain the cefditoren mother nucleus 7-ATCA. According to the synthesis process, generation of E-type impurities is reduced, and the purity of the product is improved.

The invention relates to a synthesis method of (S)-2, 2, 4-trimethyl pyrrolidine hydrochloride, which comprises the following steps: step a, carrying out Michael addition reaction on a compound 10 and a compound 11 in the presence of a solvent to prepare a compound 12; b, the compound 12 and ethyl bromoacetate are subjected to an affinity substitution reaction under the alkaline and solvent conditions, and a compound 13 is prepared; c, carrying out condensation ring closing reaction on the compound 13 under alkaline and solvent conditions to prepare a compound 14; step d, the compound 14 is subjected to a decarboxylation reaction under the acidic condition, and a compound 15 is prepared; e, the compound 15 is subjected to Wittig reaction under the alkaline condition, and a compound 16 is prepared; and step f, carrying out asymmetric hydrogenation reaction on the compound 16 to prepare a target compound 1, namely (S)-2, 2, 4-trimethylpyrrolidine hydrochloride. According to the synthetic method of the (S)-2, 2, 4-trimethylpyrrolidine hydrochloride, the reaction type of the whole synthetic route is safe, the yield of each step is relatively high, and industrial production is convenient to realize.

The application discloses a chemical synthesis method of 7-ketolithocholic acid (3alpha-hydroxy-7-keto-5beta-cholestane-24-oic acid), and belongs to the field of organic chemical synthesis. The 7-ketolithocholic acid is synthesized from a plant source compound BA through steps of glycol or neopentyl glycol protection, oxidation, Wittig reaction, deprotection, reduction and hydrolysis. The raw material used for synthesizing the 7-ketolithocholic acid is cheap and easy to obtain, the synthesis steps are simple and convenient to operate, the yield is high, the environment is friendly, and the industrialized production is facilitated.

The method comprises the following steps: taking androstane-3-ketone-4-ene-17beta-carboxylic acid shown in a formula II as a raw material, carrying out decarboxylation hydroxylation, sulfonylation, elimination and double-bond oxidative cracking to prepare the exemestane intermediate shown in a formula VI, and then sequentially carrying out allylic oxidation, wittig reaction and 1, 2, 4-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3-trimethyl-1, 3, 4-trimethyl-1, 3 the exemestane shown in the formula I is prepared through the step of 1, 2-site dehydrogenation. The method has the characteristics of simple process operation, mild conditions, high reaction yield and the like, and is suitable for industrial production.

The invention discloses a synthesis method of 6-pentyl-2H-pyran-2-ketone, which comprises the following steps: step 1, reacting n-hexanoic acid or n-hexanoyl chloride with a malonate compound to obtain a compound a; step 2, carrying out carbonyl ketal protection reaction on the compound a to obtain a compound b; 3, the compound b is subjected to a reduction reaction, and a compound c is obtained; 4, the compound c is subjected to an oxidation reaction, and a compound d is obtained; 5, the compound d is subjected to a Wittig reaction, and a compound e is obtained; step 6, hydrolyzing the compound e, and removing a protecting group to obtain a compound f; and step 7, carrying out cyclization on the compound f, so as to obtain the 6-amyl-2H-pyran-2-one. According to the method, n-hexanoic acid (or n-hexanoyl chloride) serves as a starting raw material, 6PP is prepared through decarboxylation, ketal protection, reduction, oxidation, wittig reaction, hydrolysis deprotection and cyclization, the raw materials are cheap and easy to obtain, reaction conditions are mild, and the method is environmentally friendly and suitable for industrial production.

The application belongs to the technical field of pharmaceutical synthesis chemistry, and particularly relates to a preparation method of a small molecule Id protein inhibitor AGX51. The preparation method takes a piperonal compound 5 as a starting raw material, and obtains an olefin product compound 4 through a Wittig reaction. The compound 4 is subjected to double bond epoxidation and ring-opening reaction under alkaline conditions to synthesize a compound 3. The compound 3 is subjected to a Pinacol rearrangement reaction to obtain a compound 2. The compound 2 is subjected to Wittig olefination and hydrolysis reaction in series to obtain the compound 1. The compound 1 is subjected to reduction amination and acylation reaction in sequence to complete the synthesis of AGX51 in one pot. The structure of the target product is confirmed by MS, 1 H NMR and 13 C NMR. The structures of intermediates are confirmed by 1 H NMR. Through the preparation method, the total yield of the small molecule Id protein inhibitor AGX51 is significantly improved.

The invention provides an olefine aldehyde intermediate and a synthetic method thereof, and a synthetic method of conopomorpha sinensis sex pheromone, and belongs to the field of compound synthesis. According to the synthesis method of the olefine aldehyde intermediate, provided by the invention, 1, 5-pentanediol is taken as a raw material, and the high-yield olefine aldehyde intermediate is obtained through transesterification, first oxidation reaction, Wittig reaction and Sagsa oxidation reaction; the yield of the olefine aldehyde intermediate can be further improved by limiting a catalytic system and an auxiliary agent of the Sagsa oxidation reaction. Results of the embodiment show that the synthesis method provided by the invention does not adopt alkyne compounds, the yield of the product in the Sagassa oxidation reaction stage can reach 81%, the total yield of the obtained olefine aldehyde intermediate can reach 48.5%, the sex pheromone of conopomorpha sinensis prepared by adopting the olefine aldehyde intermediate can reach 39.8%, and the yield is high.

The invention discloses a method for synthesizing a key intermediate of pilocarpine. The invention provides a method for synthesizing a key intermediate of pilocarpine. The method uses 2,2-dimethyl-1,3-dioxane-5-one as a starting material, synthesizes 4-ethyl-5-oxy-2,5-dihydrofuran-3-acetic acid through Horner-Wadsworth-Emmons olefination, hydrolysis, oxidation, Wittig reaction, hydrolysis, oxidation and the like, and then synthesizes the final product according to the steps in the document "Concise Synthesis of Both Enantiomers of Pilocarpine".

The invention relates to a total synthesis method of salvianolic acid F. The method comprises the following steps: brominating 2, 3-dimethoxybenzaldehyde to obtain 2-bromine-5, 6-dimethoxybenzaldehyde, carrying out Wittig reaction to obtain (E)-1-bromine-2-(3, 4-dimethoxystyryl)-3, 4-dimethoxybenzene, and carrying out reaction on (E)-1-bromine-2-(3, 4-dimethoxystyryl)-3, 4-dimethoxybenzene to obtain the salvianolic acid F. The preparation method comprises the following steps: taking salvianolic acid as a raw material, reacting with acrylate under the action of alkali and a palladium catalyst to obtain tetramethyl salvianolic acid F, and obtaining salvianolic acid F from the tetramethyl salvianolic acid F and a demethylation reagent. The preparation method is short in route and reasonable in process, the adopted reagent is safe, low in cost and free of environmental pollution, meanwhile, the preparation method has the advantages of simplicity in operation, easiness in separation and the like, and the obtained product is high in yield.

The invention discloses a synthetic method of tea geometrid sex pheromone (3Z, 6Z, 9Z)-octadecatriene, which comprises the following steps: carrying out bromination on cis-3-hexene-1-alcohol in a bromination system, and carrying out salt forming reaction on the brominated cis-3-hexene-1-alcohol and triphenylphosphine to obtain cis-3-hexenyl triphenylphosphonium bromide; the preparation method comprises the following steps: generating an alkynyl metal intermediate from 3-butyne-1-alcohol under the action of an organic metal reagent, and carrying out alkylation reaction on the alkynyl metal intermediate and n-octane bromide to obtain 3-dodecanol; carrying out hydrogenation reaction under the action of a catalyst, and then carrying out oxidation reaction under the action of an oxidizing agent to obtain cis-3-dodecenal; the preparation method comprises the following steps: dispersing cis-3-hexenyl triphenyl phosphonium bromide in an ether solvent, and carrying out Wittig reaction on the cis-3-hexenyl triphenyl phosphonium bromide and cis-3-dodecenal under the action of alkali to obtain the (3Z, 6Z, 9Z)-octadecatriene. The synthesis method only needs six-step reaction, the reaction condition is mild, the raw materials are cheap and easy to obtain, the yield is high, and large-scale production is easy.

The invention relates to a preparation method of flurbiprofen with low cost and high purity. The preparation method comprises the following steps: taking 4-bromine-2-fluorobiphenyl as a raw material, and carrying out Grignard reaction on the 4-bromine-2-fluorobiphenyl and magnesium powder to obtain 2-fluoro-4-biphenyl magnesium bromide; the preparation method comprises the following steps: in a solvent, enabling 2-fluoro-4-biphenyl magnesium bromide and N, N-dimethylacetamide to be subjected to a Bouveaut reaction, so as to obtain 2-fluoro-4-biphenyl ethyl ketone; the method comprises the following steps: under the action of a base catalyst, carrying out Wittig reaction on 2-fluoro-4-biphenyl ethanone and (methoxymethyl) triphenyl phosphonium chloride to obtain an alkene etherate, and carrying out acidolysis on the alkene etherate to obtain 2-(2-fluoro-4-biphenyl) propionaldehyde; and carrying out Pinnick oxidation on the 2-(2-fluoro-4-biphenyl) propionaldehyde, sodium chlorite and hydrogen peroxide to obtain racemic 2-(2-fluoro-4-biphenyl) propionic acid, namely, flurbiprofen. The process route totally comprises four steps of reactions, each step is a classical chemical reaction, the HPLC purity of the obtained flurbiprofen is greater than or equal to 99.5%, the materials are cheap and easy to obtain, the operation is simple, the post-treatment is convenient, and the method is suitable for industrial production.

The invention provides a method for producing 2-m-hydroxyphenylacetic acid and 2-m-hydroxyphenylacetic acid, which can be safely and efficiently produced. A method for producing 2-m-hydroxyphenylacetic acid according to one embodiment of the present invention comprises: a first step for generating m-hydroxystyryl methyl ether by reacting m-hydroxybenzaldehyde with a Wittig reactant represented by general formula (I) in an amount of 2 molar equivalents or more relative to the m-hydroxybenzaldehyde; a second step for generating 2-(m-hydroxyphenyl) acetaldehyde by an acid hydrolysis reaction of the m-hydroxystyryl methyl ether; and a third step in which the 2-(m-hydroxyphenyl) acetaldehyde is treated using an oxidizing agent. In addition, the method for producing 2-m-hydroxyphenylacetic acid involves performing the second step and the third step in situ. The general formula (I) is H3C-O-CH = PPh3 (I).

The invention relates to a preparation method of sacubitril, which comprises the following steps: (1) reacting (S)-1-([1, 1 '-biphenyl]-4-yl)-3-chloropropane-2-ol with succinimide under the condition of triphenylphosphine and DEAD (Diethylaminoethyl Adenine) to obtain (R)-1-(1-([1, 1'-biphenyl]-4-yl)-3-chloropropane-2-yl) pyrrolidine-2, 5-diketone; (2) adding water and an alkaline reagent into the product in the step (1) to obtain (R)-4-(([1, 1 '-biphenyl]-4-yl)-3-hydroxypropyl-2-yl)-amino-4-oxobutyric acid; (3) carrying out oxidation and wittig reaction on the product obtained in the step (2) to prepare (4R)-5-[1, 1 '-biphenyl]-4-yl-4-[(3-carboxyl-1-oxopropyl) amino]-2-methyl-2-pentenoic acid-1-ethyl ester; (4) performing palladium-carbon catalytic reaction on the product obtained in the step (3) for alkali adjustment to prepare a sacubitril sodium salt aqueous solution; and (5) performing free extraction on the sacubitril sodium salt, concentrating, adding acetone and isopropanol to prepare a mixed solution, and reacting with valsartan and sodium hydroxide to prepare the sacubitril valsartan sodium. The method is simple and convenient to operate, can obtain the product with high purity and high yield, and is suitable for industrial production.

The application provides a synthesis method and antitumor application of several furanopyrimidine-ibuprofen hybrid derivatives, which are linked by aza-wittig reaction, intramolecular cyclization, substitution reaction, hydrolysis and acidification reaction and the like, and a fused triazole, a hydrazide, a bis-hydrazide and an oxadiazole are used as a bond bridge key, so that different series of furanopyrimidine-ibuprofen hybrid derivatives are synthesized in a simple and efficient manner. The CCK8 method in vitro pharmacodynamics test proves that the target compound has proliferation inhibition activity on A549 lung cancer cells and HepG2 liver cancer cell lines. Test results show that the target compound shows good proliferation inhibition activity on the two kinds of cells, and the structural formula is as follows:

The invention discloses a composite absorbent for capturing carbon dioxide in flue gas and application of the composite absorbent, and relates to the technical field of carbon dioxide composite absorbents. The flue gas CO2 trapping composite absorbent and the matched macromolecular anti-degradation agent disclosed by the invention have efficient absorptivity, strong degradation resistance and industrial suitability, the material takes aminoethylethanolamine as a main absorbent and is matched with a 2-amino-2-methyl-1-propanol auxiliary absorbent and an N-methylpiperazine activator, and high CO2 selectivity is realized through mass ratio optimization; the anti-degradation agent is prepared by compounding a bismuth reagent and a macromolecular anti-degradation agent, the macromolecular anti-degradation agent is subjected to a Witt ig reaction, a thiol click reaction and other multi-step processes, active units such as hindered phenol, benzotriazole and acetaldoxime are integrated, free radicals can be removed, metal ions can be passivated, NOx can be neutralized, the amine degradation rate is reduced, and an efficient, stable and economical solution is provided for CO2 trapping.

The invention belongs to the field of medicinal chemistry, and particularly provides a synthesis method of a key intermediate of suzertraline, 3, 4-difluoro-2-methoxybenzaldehyde is used as a starting material, and 3, 4-difluoro-2-methoxyphenylacetic acid is obtained through Wittig reaction, demethylation and aldehyde group oxidation. Compared with the prior art, the synthesis yield of the synthesized target compound is high, the synthesis process is simple to operate, the use of an expensive catalyst is avoided, the method is environment-friendly, the production is efficient, the synthesis purity is high, and factory amplification-scale production is facilitated.

The invention provides a synthesis method of cefepime starting material oxidation impurities, and belongs to the field of medicinal chemistry. The cefepime is prepared by modifying a 7-site amino side chain of D-7-ACA, oxidizing a 3-site hydroxyl, carrying out wittig reaction with a starting material, and then carrying out deprotection. When the starting material is subjected to wittig reaction, the ylide generated by the starting material can be oxidized to generate oxidized impurities. The method comprises the following steps: reacting a cefepime starting material with a strong base to generate a ylide intermediate, and continuously introducing new oxygen into the ylide intermediate to prepare the cefepime starting material oxide impurity. The preparation and separation method of the cefepime starting material oxidation impurity provided by the invention has the advantages of simplicity in operation, environmental friendliness, low cost and high purity of the obtained impurity, and lays a good foundation for quality research and control of cefepime.

The invention discloses a synthesis method of a diene liquid crystal monomer, which comprises the following steps: S1, Grignard addition reaction: carrying out Grignard addition reaction on substituted cyclohexyl N-methoxy-N-methyl benzamide and a substituted cyclohexyl methyl chloride Grignard reagent to obtain a ketone intermediate; s2, the ketone intermediate sequentially reacts with 5, 5-dibromobarbituric acid for a bromination reaction, then sodium formate is added into an alcohol solvent for a hydroxylation reaction, then sodium borohydride is added for a reduction reaction, and a vicinal diol intermediate is obtained; and S3, carrying out an orthoformate reaction on the vicinal diol intermediate obtained in the step S2 and triethyl orthoformate in a fluorine-containing alcohol solvent, then heating to reflux, and carrying out an elimination reaction to obtain the target diene liquid crystal monomer. According to the invention, a traditional double bond construction strategy of multiple Wittig reactions is abandoned, a new synthesis route which takes the Grignard reaction as a starting point and finally constructs a diene structure by a one-pot method through a low-temperature orthoformate / elimination reaction carried out in a specific fluorine-containing solvent is designed, the route is simple, the total yield is high, and the overall cost is lower.

The invention discloses synthesis and antitumor activity research of a novel drug small molecular formula (1) containing an adamantane structure. According to the invention, 1-bromoadamantane is used as an initial raw material, 2-(4-((3R, 5R, 7R)-adamantane-1-yl)-2-nitrophenoxy) acetic acid is generated through a typical Friedel-Crafts alkylation reaction, an NBS bromination reaction and the like, and then an important intermediate compound 5 is synthesized through a Wittig reaction and a hydrolysis reaction. And carrying out coupling reaction on the intermediate compound 6 and different amine compounds to obtain eight target compounds 7a-7h: formula (1). A CCK-8 experiment is carried out on a target compound to obtain a conclusion that the target compound 7a-7f and 5-fluorouracil are tested at the concentration of 20 mu M, and the result shows that the compound 7c has the best inhibition effect on HeLa and A549 cells, and the compound 7e has the better inhibition effect on Hep G2 cells. IC50 value calculation is carried out on a target compound under various concentrations, the IC50 value of 7c on HeLa and A549 cells is minimum and the inhibition effect is best, and the IC50 value of 7e on Hep G2 cells is minimum and the inhibition effect is best.

The application discloses a novel method for preparing an intermediate of an aryl abietane diterpene Plebein C, and specifically comprises the following steps: substituting a carbonyl alpha position of 4,4-dimethyl-2-cyclohexen-1-ketone to obtain compound I; protecting the compound I by TBS to obtain compound II; performing a Luche reduction reaction on the compound II to obtain compound III; performing an iodination reaction on 3-hydroxy-4-methoxybenzaldehyde to obtain compound IV; performing a Wittig reaction on the compound IV to obtain compound V; performing a Mitsunobu reaction between the compound III and the compound V to obtain compound VI; performing a radical cyclization reaction on the compound VI to obtain compound VII; performing an oxidation on a benzyl position of the compound VII to obtain compound VIII; and finally performing an oxidation and a ring closure on the compound VIII to obtain a five-ring intermediate compound IX of a Plebein C molecule; the preparation method has the advantages of simple synthetic route, low-cost and easily-obtained reagents, high yield, favorability for industrial preparation of the intermediate, and strong popularization potential.

The present invention discloses a novel alkaloid derivative, its synthesis method and application. Based on the active pregnane-type alkaloid skeleton structure in the Miao medicine "Sanyangyin", using epiandrosterone as a raw material, a series of C20-oxime pregnane-type alkaloid derivatives are obtained through reactions such as Wittig reaction, reduction reaction, Corey oxidation, reductive amination, and N-alkylation. This method has a simple and efficient preparation process and mild reaction conditions. The synthesized C20-oxime pregnane-type alkaloid derivatives have excellent anti-tumor activity and anti-inflammatory properties and can be used in anti-tumor and anti-inflammatory drugs. It provides a scientific basis for the new drug development and application of novel anti-tumor and anti-inflammatory pregnane-type alkaloids.