» Articles » PMID: 23833707

7-Aza-des-A-steroids with Antimicrobial and Cytotoxic Activity

Overview
Journal Sci Pharm
Publisher MDPI
Specialty Pharmacology
Date 2013 Jul 9
PMID 23833707
Citations 2
Authors
Affiliations
Soon will be listed here.
Abstract

This paper describes a convenient approach to the 7-aza-des-A-steroid (6,6a,7,8,9,9a-hexahydro-5H-cyclopenta[h]quinoline) scaffold starting from Grundmann's ketone using two different pyridine annulation protocols. The biological evaluation of the pyridine and pyridinium products revealed that these compounds unexpectedly do not interfere with ergosterol and cholesterol biosynthesis. The pyridinium compound 6 showed significant antimicrobial and cytotoxic activities which are most likely due to its detergent-like structure.

Citing Articles

Recent Advances in Vitamin D3 Intervention to Eradicate Infection.

Ma P, Zhuo L, Yuan L, Qi X J Multidiscip Healthc. 2024; 17:825-832.

PMID: 38434485 PMC: 10906669. DOI: 10.2147/JMDH.S454605.


Identification and characterization of a vitamin D₃ decomposition product bactericidal against Helicobacter pylori.

Hosoda K, Shimomura H, Wanibuchi K, Masui H, Amgalanbaatar A, Hayashi S Sci Rep. 2015; 5:8860.

PMID: 25749128 PMC: 4352922. DOI: 10.1038/srep08860.

References
1.
Zanati G, WOLFF M . Synthesis of an androgenic-anabolic nonsteroid. J Med Chem. 1973; 16(1):90-1. DOI: 10.1021/jm00259a028. View

2.
Wollein U, Bracher F . The gramine route to pyrido[4,3-b]indol-3-ones - identification of a new cytotoxic lead. Sci Pharm. 2011; 79(1):59-68. PMC: 3097496. DOI: 10.3797/scipharm.1011-11. View

3.
Singh H, Jindal D, Yadav M, Kumar M . Heterosteroids and drug research. Prog Med Chem. 1991; 28:233-300. DOI: 10.1016/s0079-6468(08)70366-7. View

4.
Konig M, Muller C, Bracher F . Stereoselective synthesis of a new class of potent and selective inhibitors of human Δ8,7-sterol isomerase. Bioorg Med Chem. 2013; 21(7):1925-43. DOI: 10.1016/j.bmc.2013.01.041. View

5.
Giera M, Renard D, Plossl F, Bracher F . Lathosterol side chain amides: a new class of human lathosterol oxidase inhibitors. Steroids. 2008; 73(3):299-308. DOI: 10.1016/j.steroids.2007.10.015. View