Synthesis of novel steroidal D-ring substituted isoxazoline derivatives of 17-oxoandrostanes

Banday, Abid H.; Singh, Swarn; Alam, Mohammad Mahboob; Reddy, D. Mahendhar; Gupta, B. D.; Kumar, Halmuthur M. Sampath

doi:10.1016/j.steroids.2007.10.014

Cited by 29 publications

(8 citation statements)

References 14 publications

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“…It is apparent from the present study that a group of steroid compounds from the plant extracts can alter the electrical functions of the heart through inhibition of Na + /K + -ATPase. Consequently, there is increased Na + / Ca ++ exchange leading to an increase of calcium entry (Katzung & Parmely, 2001;Banday et al, 2008). In addition, the cardiac glycosides examined in the present study decreased the heart rate (negative chronotropic effect), thereby suggesting therapeutic potential during cardiac failure that is commonly accompanied by ventricular tachycardia.…”

Section: Discussionmentioning

confidence: 60%

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Extraction and phytochemical investigation ofCalotropis procera: Effect of plant extracts on the activity of diverse muscles

Moustafa

Ahmed

Nabil

et al. 2010

Pharmaceutical Biology

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Section: Discussionmentioning

confidence: 60%

“…Two flavonoid constituents were isolated from this plant, which are known as rutin and quercetin 3-O-galactoside (Wheeler et al, 2003). It is known that C. procera is considered a source of digitalis-like therapeutic agents and is highly toxic to the land snail Thepa pisana (Muller) (Choedon et al, 2006;Banday et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

Extraction and phytochemical investigation ofCalotropis procera: Effect of plant extracts on the activity of diverse muscles

Moustafa

Ahmed

Nabil

et al. 2010

Pharmaceutical Biology

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“…For a general introduction to steroids functionalized with heterocycles, see: Banday et al (2008); Pathak & Jindal (1998); Litvinovskaya et al (1998); Beam et al (2000). For the biological activity of danazol, a steroid sharing structural features with the title compound, see: Gupta et al (1999).…”

Section: Related Literaturementioning

confidence: 99%

(20S,2′′S)-20-[4′-(3′′-Hydroxy-2′′-methylpropyl)-3′-methylisoxazol-5-yl]-5β-pregnan-3β,16β-diol

Linares¹,

Ramírez

Meza‐Reyes

et al. 2009

Acta Cryst E

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The title steroidal compound, C29H47NO4, was prepared in a one-pot reaction starting from a sarsasapogenin derivative of known configuration. The isoxazole heterocycle is oriented towards the α face of the steroid nucleus and, although fully functionalized on C atoms, does not provoke steric hindrance with the adjacent D ring. The absolute configuration observed for chiral centers is as expected, and shows that no epimerization occurred in the precursors. In the crystal, the three OH groups serve as donors for hydrogen bonding with O and N atoms. The isoxazole N atom is involved in O—H⋯N hydrogen bonds, forming chains along [100]. These chains are further connected via O—H⋯O and weak C—H⋯O contacts, giving rise to a three-dimensional supramolecular network.

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“…In this regard, different derivatives of androsterone (3α-hydroxy-5α-androstan-17-one) have been excessively studied as potent anti-cancer agents (Figure 1) [18,19]. Recently, the significant cytotoxic and aromatase inhibitory potential of a large number of androsterone derivatives containing substitution at position 16 have been reported [12,20,21].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In vitro cytotoxic activity evaluation of (E)-16-(substituted benzylidene) derivatives of dehydroepiandrosterone

et al. 2013

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Background and the purpose of the studyModified androsterone derivatives are class of steroidal compounds with potential anticancer properties. Various steroidal derivatives containing substitution at position 16 have shown diversified pharmacological activities. In the present study, a new series of cytotoxic 16-(substituted benzylidene) derivatives of dehydroepiandrosterone (DHEA) were synthesized and evaluated against three different cancer cell lines.MethodsThe cytotoxic 16-(substituted benzylidene) derivatives of DHEA were synthesized via aldol condensation of DHEA with corresponding benzaldehyde derivatives. The cytotoxic activity of synthesized derivatives was evaluated against three different cancer cells including KB, T47D and SK-N-MC cell lines by MTT reduction colorimetric assay.ResultsThe results indicated that 16-(substituted benzylidene) derivatives of DHEA could be served as a potent anti-cancer agent. The 3-cholro benzylidene derivatives of DHEA was the most potent synthesized derivative especially against KB and T47D cell lines (IC50 values were 0.6 and 1.7 μM; respectively).ConclusionThe cytotoxic potential of novel benzylidene derivatives of DHEA is mainly attributed to the position and nature of the substituted group on the benzylidene pendant.

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Synthesis of novel steroidal D-ring substituted isoxazoline derivatives of 17-oxoandrostanes

Cited by 29 publications

References 14 publications

Extraction and phytochemical investigation ofCalotropis procera: Effect of plant extracts on the activity of diverse muscles

Extraction and phytochemical investigation ofCalotropis procera: Effect of plant extracts on the activity of diverse muscles

(20S,2′′S)-20-[4′-(3′′-Hydroxy-2′′-methylpropyl)-3′-methylisoxazol-5-yl]-5β-pregnan-3β,16β-diol

Synthesis and In vitro cytotoxic activity evaluation of (E)-16-(substituted benzylidene) derivatives of dehydroepiandrosterone

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