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[0005] However, this class of drugs has the following obvious disadvantages (SchnellJR, ChouJJ.Nature.2008, 451(7178):591-5): (1) Ineffective against influenza B virus; (2) There are obvious side effects, causing obvious gastrointestinal side effects of the central nervous system, mainly manifested as insomnia, distraction and nervousness; (3) Drug-resistant strains are prone to be produced during treatment
Although decades have passed since the two single-skeleton drugs were launched, no drugs with new structures have emerged. Most of the inhibitors in research drugs still use adamantane as the backbone, so it is urgent to find drugs with new structures. Inhibitor
Method used
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Embodiment 1
[0042] Embodiment 1: the general synthetic procedure of compound 1-10:
[0043] in CH 3 After dissolving (1R,2R,3R,5S)-(□)-pinamine (1g, 6.5mmol) in OH (20mL), add aldehyde or ketone (1.5equiv., 9.8mmol), and stir the reaction solution at room temperature for 1h , followed by NaBH(OAc) 3 (5.5g, 26mmol), after adding 1 drop of acetic acid dropwise, the reaction was stirred for 10h. Then, saturated sodium bicarbonate solution was added to quench the reaction, extracted with dichloromethane (3x20ml), the combined organic phases were washed twice with saturated brine, and dried over anhydrous sodium sulfate. The oil obtained by column chromatography was washed with HCl / CH 3 After treatment with OH (20 mL), evaporation to dryness resulted in a solid that was washed with ether (3x20 mL) to give the title compound.
Embodiment 2
[0044] Example 2: (1R,2R,3R,5S)-2,6,6-trimethyl-N-((5-methyl-1H-4-imidazolyl)methyl)bicyclo[3.1.1] Heptane-3-amine (Compound 1)
[0047] Example 3: (1R,2R,3R,5S)-2,6,6-trimethyl-N-((5-cyclopropyl-1H-4-imidazolyl)methyl)bicyclo[3.1.1 ]heptane-3-amine (compound 2)
[0048]
[0049] 1 HNMR (400MHz, DMSO-d 6 )δ0.92(s,3H),1.01(d,2H,J=8.8Hz),1.12(s,3H,J=7.2),1.17 1.20(m,6H),1.75 1.81(m,2H),1.90 1.97(m,2H),2.00 2.07(m,3H),3.53(s,1H),4.36(s,2H),8.27(br,1H),9.03(d,1H,J=8),9.57(br ,1H),10.13(br,1H),14.66(br,1H);ESI-MS:calculatedforC 17 h 27 N 3 (M+H + ):274.42,found:274.3.
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Abstract
Disclosed is a cycloalkylamine compound of formula (I) useful in resisting mutant influenza virus, wherein n is independently selected from 0, 1; R1 is selected from H, alkyl, cycloalkyl, heterocyclic alkyl, aryl, imidazolyl, heteroaryl, aralkyl, heteroaryl alkyl, or aryl heterocyclic radical; R2 and R3 are independently selected from H, alkyl, cycloalkyl, heterocyclic alkyl, amidino, guanidino, amidinoguanidino, imidazolyl, 2-thienyl, 3-thienyl, furyl, acyl, aryl, heteroaryl, araklyl, heteroaryl alkyl, aryl heterocyclic radical, arylthio, or arylthio alkyl. The compound inhibits cell pathological changes and cell death by inhibiting virus replication by blocking M2 ion channels.
Description
technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a novel cycloalkane amine compound for resisting mutant influenza virus. Background technique [0002] Influenza (hereinafter referred to as influenza) is an acute respiratory infectious disease that seriously endangers human health. It is caused by influenza virus and has the characteristics of high prevalence, widespread prevalence and rapid transmission. There have been many worldwide influenza pandemics in history, among which the Spanish flu epidemic in 1918 was the most serious, and more than 20 million people were killed by influenza. In 2009, the "swine flu" that broke out in Mexico is now seriously threatening the lives of human beings all over the world, causing great losses to human life and social economy. [0003] At present, the main means of preventing and treating influenza are M2 ion channel protein inhibitors, neuraminidase inhibitors and influenz...
Claims
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