Synthesis and antituberculosis activity of certain steroidal derivatives of the 5α-series

Merlani, Maia; Amiranashvili, Lela; Mulkidzhanyan, K. G.; Shelar, A. R.; Manvi, F. V.

doi:10.1007/s10600-008-9126-8

Cited by 10 publications

(7 citation statements)

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“…In the continuation of our research on new bioactive N-containing 5α-steroids, ten steroidal hydrazine derivatives, that we synthesized earlier on the basis of steroidal ketones [ 25 , 26 , 27 , 28 , 29 ], and two new compounds were prepared and evaluated for their antibacterial and antifungal actions.…”

Section: Resultsmentioning

confidence: 99%

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Antimicrobial Activity of Some Steroidal Hydrazones

et al. 2023

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Twelve steroid based hydrazones were in silico evaluated using computer program PASS as antimicrobial agents. The experimental evaluation revealed that all compounds have low to moderate antibacterial activity against all bacteria tested, except for B.cereus with MIC at a range of 0.37–3.00 mg/mL and MBC at 0.75–6.00 mg/mL. The most potent appeared to be compound 11 with MIC/MBC of0.75/1.5 mg/mL, respectively. The evaluation of antibacterial activity against three resistant strains MRSA, E.coli and P.aeruginosa demonstrated superior activity of compounds against MRSA compared with ampicillin, which did not show bacteriostatic or bactericidal activities. All compounds exhibited good antifungal activity with MIC of 0.37–1.50 mg/mL and MFC of 1.50–3.00 mg/mL, but with different sensitivity against fungi tested. According to docking studies, 14-alpha demethylase inhibition may be responsible for antifungal activity. Two compounds were evaluated for their antibiofilm activity. Finally, drug-likeness and docking prediction were performed.

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Section: Resultsmentioning

confidence: 99%

“…Encouraged by these observations, and based on our previous work [ 25 , 26 , 27 ], herein we report the synthesis of two novel 5α-steroidal hydrazones and the evaluation of antimicrobial activity of newly and earlier synthesized compounds.…”

Section: Introductionmentioning

confidence: 94%

Antimicrobial Activity of Some Steroidal Hydrazones

et al. 2023

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“…Taking this into account, we synthesized various new steroidal INH [6] and other derivatives. The goal of the present study was to compare the antimycobacterial activity of the previously and newly synthesized compounds.Starting ketosteroids (2-9) were prepared from tigogenin (1) that was isolated from Yucca gloriosa L. by the published method [3][4][5][6][7][8]. Steroidal hydrazones (10-18) were prepared by condensation of isoniazide [3, 5, 6], m-nitrobenzoic acid hydrazide, and m-bromobenzoic acid hydrazide with steroidal skeletons (2-9).…”

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confidence: 99%

“…We reported previously on the antimycobacterial activity of some 5α-steroidal INH in vitro [3][4][5]. It was found that some of them were just as active toward M. tuberculosis as isoniazide.…”

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Synthesis and antimycobacterial activity of some steroidal derivatives of tigogenin

et al. 2009

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Some 5α-type steroidal derivatives of the steroidal sapogenin tigogenin were synthesized. The structures of the synthesized derivatives were characterized by spectral methods and elemental analysis. The antituberculosis activity of the compounds toward Mycobacterium tuberculosis strain H37Rv was studied in vitro (Microplate Alamar Blue Assay) in BACTEC 12B medium and was compared with that of isoniazide. Some of the synthesized compounds exhibited high (92-98%) antimycobacterial activity.Key words: antimycobacterial activity, 5α-steroidal hydrazones, 5α-aminosteroids.Changes of various social, medical, and economic factors at the end of the 1980s caused tuberculosis to start again to spread. The emergence of resistant strains of the disease that exposed the imperfection of the modern arsenal of drugs enhanced the rebound of tuberculosis [1]. The need arose to create new drugs that could be used in shorter treatment courses than existing drugs in order to treat resistant and latent forms of the disease.It was recently proposed that the mechanism of resistance to isoniazide, which remains to this day the first-line drug, is related to mutation or deletion of peroxidase catalase KatG and that antibacterial resistance to the drug can be overcome by synthesizing new isoniazide derivatives, in particular, by preparing biologically different forms of this drug, namely hydrazones. Nevertheless, isonicotinoylhydrazones (INH) themselves are viewed as compounds with potential antituberculosis activity [2].We reported previously on the antimycobacterial activity of some 5α-steroidal INH in vitro [3][4][5]. It was found that some of them were just as active toward M. tuberculosis as isoniazide. Taking this into account, we synthesized various new steroidal INH [6] and other derivatives. The goal of the present study was to compare the antimycobacterial activity of the previously and newly synthesized compounds.Starting ketosteroids (2-9) were prepared from tigogenin (1) that was isolated from Yucca gloriosa L. by the published method [3][4][5][6][7][8]. Steroidal hydrazones (10-18) were prepared by condensation of isoniazide [3, 5, 6], m-nitrobenzoic acid hydrazide, and m-bromobenzoic acid hydrazide with steroidal skeletons (2-9). An aminosteroid (19) was synthesized from epiandrosterone acetate (6) as before [7] (Scheme 1).The structures of the newly synthesized compounds 17 and 18 were confirmed by IR, MS, PMR, and 13 C NMR spectral data.IR spectra of 17 and 18 exhibited absorption bands in the range 3400-3360 cm −1 that were characteristic for NH. Bands at 2946-2924 were assigned to the aliphatic part. The absorption band of HNC=O appeared at 1736 and 1705, respectively. The C=N band in both instances appeared at 1641; the aromatic part, 1550. The IR spectrum of 17 showed absorption bands at 1518 and 1335 (Ar-NO 2 ); of 18, 750 (Ar-Br). Resonances of angular 18-and 19-methyls in PMR spectra of 17 and 18 were singlets at δ 0.82-0.88 ppm. The methyl of the C-3 acetyl resonated at 1.97; axial 3α-H of 3α-steroidal esters, as a...

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“…In the literature, a small number of steroid azides similar to those investigated by us can be found. The synthesis and antituberculosis activity of 17α-azido-5α-androstan-3β-ol was investigated by Merlani et al [Merlani et al 2008]. The neuroactive 17αand 17β-azido-5β-androstan-3α-ol were studied by Vidrna et al [Vidrna et al 2011].…”

Section: Aromatase Inhibitory Effect Of Azido Compoundsmentioning

confidence: 99%

In vitro inhibition of the estrogen biosynthesis enzyme system with new steroid derivatives

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Synthesis and antituberculosis activity of certain steroidal derivatives of the 5α-series

Cited by 10 publications

References 3 publications

Antimicrobial Activity of Some Steroidal Hydrazones

Antimicrobial Activity of Some Steroidal Hydrazones

Synthesis and antimycobacterial activity of some steroidal derivatives of tigogenin

In vitro inhibition of the estrogen biosynthesis enzyme system with new steroid derivatives

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