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Phenylindole compound and preparation method and application thereof
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A kind of compound and alkyl technology, applied in phenylindole compound and its preparation and application field
Active Publication Date: 2016-07-06
SHENYANG PHARMA UNIVERSITY
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But clinically used tamoxifen and raloxifene can cause adverse reactions such as endometrial cancer and hot flashes (FisherB, CostantinoJP, WickerhamDL, et al.JNatiCancerInst, 1998, 90:1371-1388; WalshBW, KullerLH, WildRA , et al. JAmMedAssoc, 1998, 279:1445-1451)
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Embodiment 1
[0035] Example 1: Preparation of 1-[4-(dimethylamino)butyl]-5-benzyloxy-2-(4-benzyloxyphenyl)-3-methyl-1H-indole
[0036] Step A): Preparation of 4-nitrobenzyloxybenzene
[0037] Put 4-nitrophenol (20.0g, 0.152mol) and anhydrouspotassiumcarbonate (131.1g, 0.950mol) in a 1000mL flask, use acetone as solvent, add dropwise benzyl chloride (12.0g, 0.095mol), and reflux reaction After 24 hours, the solvent was evaporated under reduced pressure, the residue was stirred with water, filtered with suction, and dried to obtain 19.8 g of a light yellow solid with a yield of 90.8%. m.p.105-106°C. ESI-MS: m / z139 ([M+H] + ).
[0038] Step B): Preparation of 4-benzyloxyaniline
[0039] Put 4-nitrobenzyloxybenzene (10.0g, 0.044mol) and tin protochloride (50g, 0.220mol) in a 1000mL round bottom flask, ethanol as solvent, N 2 Under protection, react at 45°C for 24h. Evaporate the solvent under reduced pressure, transfer the residue to a 1000mL beaker with 600mL of sodiumcarbonate solut...
Embodiment 2
[0052] Example 2: Preparation of 1-[4-(diethylamino)butyl]-5-benzyloxy-2-(4-benzyloxyphenyl)-3-methyl-1H-indole
[0053] According to the method of Example 1, 0.39 g of a yellow solid was obtained with a yield of 38.9%. m.p.102-103°C. ESI-MS: m / z367 ([M+H] + ). 1 H-NMR (400MHz, DMSO-d 6 )δ9.67(s,1H),8.68(s,1H),7.24(d,J=8.7Hz,1H),7.19(d,J=8.5Hz,2H),6.90(d,J=8.5Hz, 2H), 6.79(d, J=2.2Hz, 1H), 6.64(dd, J 1 =8.6Hz,J 2 =2.3Hz,1H),3.98(t,J=6.4Hz,2H),3.34(m,6H),2.05(s,3H),1.5(d,J=5.1Hz,4H),1.87(m,6H ).
Embodiment 3
[0054] Example 3: Preparation of 1-[4-(isopropylamino)butyl]-5-benzyloxy-2-(4-benzyloxyphenyl)-3-methyl-1H-indole
[0055] According to the method of Example 1, 0.30 g of a yellow solid was obtained with a yield of 52.1%. m.p.116-117°C. ESI-MS: m / z353 ([M+H] + ),375([M+Na] + ). 1 H-NMR (400MHz, DMSO-d 6 )δ9.05(s,1H),8.12(s,1H),7.25(d,J=8.6Hz,1H),7.17(d,J=8.4Hz,2H),6.88(d,J=8.4Hz, 2H), 6.81(d, J=2.2Hz, 1H), 6.64(dd, J 1 =8.7Hz,J 2 =2.3Hz,1H),4.09(s,1H),3.97(t,J=6.8Hz,2H),3.52(m,1H),2.06(s,2H),2.04(s,3H),1.54(m ,4H), 1.24(s,6H).
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Abstract
The invention belongs to the technical field of medicines, and relates to a phenylindole derivative and application thereof.The phenylindole derivative comprises stereisomer and pharmaceutically-applicable salt of a phenylindole compound and has the structural formula (please see the formula in the description).The phenylindole derivative and the acid-added pharmaceutically-applicable salt of the phenylindole compound can be used in cooperation with existing medicines or used independently as an estrogenreceptorregulator for treating or preventing various diseases related to estrogen functions such as bone loss, fractures, bone rarefaction, hectic fever, LDL cholesterol level rise, cardiovascular diseases, cognitive deficits, brain degeneration diseases, anxiety, depression caused by estrogen deficiency, sexual dysfunction, hypertension, retinal degeneration, cancers and especially osteoporosis.
Description
technical field [0001] The present invention relates to phenylindole compound and its preparation method, and its application in the preparation of estrogen receptorregulatormedicine. Background technique [0002] Compounds that mimic estrogen-like effects have a wide range of therapeutic and prophylactic applications, including: treatment of osteoporosis, relief of menopausal symptoms, treatment of acne, treatment of dysmenorrhea and dysfunctional uterine bleeding, prostatecancer and prevention of cardiovascular disease. [0003] Studies have found that there are two types of estrogen receptors (ER): ERα and ERβ. After the ligand binds to these two isoforms, it exerts physiological effects with different tissue specificities. [0004] What is needed in the art is a compound that can produce a positive response like estrogen replacement therapy but without adverse side effects or with reduced side effects, and exert tissue-specific estrogen-like effects on the body. Phe...
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