+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

1H-indazole and 2H-indazole derivatives of androsta-5,16-dien-3beta-ol

1H-indazole and 2H-indazole derivatives of androsta-5,16-dien-3beta-ol

Acta Crystallographica. Section C Crystal Structure Communications 64(Pt 4): O217

The title compounds, 17-(1H-indazol-1-yl)androsta-5,16-dien-3beta-ol, (I), and 17-(2H-indazol-2-yl)androsta-5,16-dien-3beta-ol, (II), both C(26)H(32)N(2)O, have an indazole substituent at the C17 position. The six-membered B ring of each compound assumes a half-chair conformation. A twist of the steroid skeleton is observed and reproduced in quantum-mechanical ab initio calculations of the isolated molecule using a molecular orbital Hartree-Fock method. In the 1H-indazole derivative, (I), the molecules are joined in a head-to-head fashion via O-H...O hydrogen bonds, forming chains along the a axis. In the 2H-indazole derivative, (II), the molecules are joined in a head-to-tail fashion with one of the N atoms of the indazole ring system acting as the acceptor. The hydrogen-bond pattern consists of zigzag chains running along the b axis. Substituted steroids have proven to be effective in inhibiting androgen biosynthesis through coordination of the Fe atoms of some enzymes, and this study shows that indazole-substituted steroids adopt twisted conformations that restrict their intermolecular interactions.

Please choose payment method:

(PDF emailed within 0-6 h: $19.90)

Accession: 051030480

Download citation: RISBibTeXText

PMID: 18391393

DOI: 10.1107/s0108270108005842

Related references

Reaction of dichloroketene and sulfene with n n disubstituted alpha aminomethyleneketones synthesis of pyrano 2 3 e indazole and 1 2 oxathiino 6 5 e indazole derivatives. Journal of Heterocyclic Chemistry 21(2): 361-368, 1984

Identification of three cannabimimetic indazole and pyrazole derivatives, APINACA 2H-indazole analogue, AMPPPCA, and 5F-AMPPPCA. Drug Testing and Analysis 9(2): 248-255, 2017

Synthesis of 3beta-hydroxy-androsta-5,7-dien-17-one from 3beta-hydroxyandrost-5-en-17-one via microbial 7alpha-hydroxylation. Steroids 74(2): 233-237, 2009

Nmr Studies in the Heterocyclic Series. Xxiii. - 13 C Spectra of Indazole and 3-Azido-Indazole in Acidified Dimethylsulfoxid Solutions. Spectroscopy Letters 12(11-12): 809-814, 1979

Isomeric [RuCl2(dmso)2(indazole)2] complexes: ruthenium(II)-mediated coupling reaction of acetonitrile with 1H-indazole. Dalton Transactions 2005(14): 2355-2364, 2005

N1-substituted 1H-indazole-3-ethyl carboxylates and 1H-indazole-3-hydroxamic acids. Il Farmaco; Edizione Scientifica 36(5): 315-333, 1981

Structure-activity relationships, and drug metabolism and pharmacokinetic properties for indazole piperazine and indazole piperidine inhibitors of ROCK-II. Bioorganic and Medicinal Chemistry Letters 17(8): 2355-2360, 2007

Pharmacokinetic study of sodium trans[tetrachlorobis(1H-indazole)-ruthenate (III)]/-indazole hydrochloride (1:1.1) (FFC14A) in patients with solid tumors. International Journal of Clinical Pharmacology and Therapeutics 47(1): 58-60, 2009

Reaction of Indazole with Terminal Dibromoalkanes and Their Subsequent Thermal Cyclization: A Facile Entry into Fused Indazole Ring Systems. Synthetic Communications 35(3): 409-415, 2005

Synthesis, spectral analysis, antibacterial and antifungal activities of some 4,6-diaryl-4,5-dihydro-3-hydroxy-2[H]-indazole-a novel fused indazole derivative. Journal of Enzyme Inhibition and Medicinal Chemistry 23(6): 974-979, 2008

Synthese de l'indazole-1-15N, de l'indazole-2-15N et de leurs derives n-methyles. Journal of Labelled Compounds and Radiopharmaceuticals 18(7): 999-1008, 1981

Indazole-3-oles and indazole-2-ones with anti-inflammatory activity. Die Pharmazie 55(11): 857, 2000

Identification and characterization of an indazole-3-carboxamide class synthetic cannabinoid: 2-[1-(cyclohexylmethyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoic acid (DMBA-CHMINACA). Forensic Science International 291: 167-174, 2018

Counter irritation and 6 sulfanilamido indazole pharmaco kinetics in 6 sulfanilamido indazole arthritis of rats. Drugs under Experimental and Clinical Research 7(2): 95-98, 1981

Formation of [17-2H]androsta-5,16-dien-3beta-ol from [17,21,21,21]pregnenolone by the microsomal fraction of boar testis. Biochimica et Biophysica Acta 450(3): 441-449, 1976