Synthesis, antiproliferative, acute toxicity and assessment of antiandrogenic activities of some newly synthesized steroidal lactams

Dhingra, Neelima; Bhardwaj, T. R.; Mehta, Neeraj; Mukhopadhyay, Tapas; Kumar, Ashok; Kumar, Manoj

doi:10.1016/j.ejmech.2010.01.064

Cited by 22 publications

(8 citation statements)

References 42 publications

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“…Der Samen des Bockshornklees enthält eine große Anzahl bioaktiver Substanzen, wie Alkaloide, Flavonoide, Saponine und steroidale Sapinogene [10,11]. Der Wirkmechanismus des Bockshorn- kleesamens ist zwar nicht bis ins Detail bekannt, es wurde jedoch gezeigt, dass ein Inhaltsstoff des Bockshornsamens, das Diosgenin, östrogene Wirkung aufweist [12,13]. Folglich wird Testosteron vermehrt zu Östradiol metabolisiert und dadurch wiederum die haarwurzelschädigende Bildung von Dihydrotestosteron (DHT) vermindert [14 -17].…”

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Nutritive Beeinflussung des Haarwachstums

Moers‐Carpi¹

2011

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Section: Verträglichkeitunclassified

Nutritive Beeinflussung des Haarwachstums

Moers‐Carpi¹

2011

Akt Dermatol

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“…In contrast to the well-known bisnorcholanic lactones, the corresponding lactams, to the best of our knowledge, have not been reported in the literature yet. Many biologically active lactams have been isolated from natural sources and some of them are used, along with different synthetic lactam compounds, in contemporary medicine [19][20][21][22][23][24][25][26]. Herein, we report the results of our study on the first synthesis of (16S,20S)-3β-hydroxy-5α-pregnane-20,16-carbolactam and its N-alkyl derivatives (bisnorcholanic lactams).…”

Section: Introductionmentioning

confidence: 99%

A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives

et al. 2020

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A concise synthesis of (16S,20S)-3β-hydroxy-5α-pregnane-20,16-carbolactam from tigogenin via the corresponding lactone is described. The most efficient synthetic route consisted of the lactone ring-opening with aminoalane reagent followed by PDC or Dess-Martin oxidation. The oxo-amide obtained was subjected to cyclization with Et3SiH/TFA or Et3SiH/Bi(TfO)3. Alternately, the lactone was converted first to the oxo-acid, which was then subjected to the microwave-assisted reductive amination. N-Alkyl derivatives were also obtained in a similar way.

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“…The synthesis of some aza-homosteroid compounds with unusual and interesting structures had been reported recently [9,10,11,12,13,14]. These compounds exhibited cytotoxic, antibacterial, antileukemic, and antiandrogenic activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents

et al. 2014

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Using analogues of some marine steroidal oximes as precursors, a series of aza-B-homocholestane derivatives possessing different substituted groups at the 3-position of the steroidal nucleus were synthesized. Their biological activity against cancer cell proliferation was determined with multiple cancer cell lines. Aza-B-homocholestane derivatives possessing 3-hydroxyl, 3-hydroximino and 3-thiosemicarbazone groups displayed remarkable cytotoxicity to cancer cells via apoptosis inducing mechanism. Compounds 5, 10, 12, 15 and 18 exhibited better potency to inhibit cancer cell proliferation. In addition, compound 15 was further evaluated with three dimensional (3D) multicellular spheroids assay to determine its potency against spheroid growth. The structure-activity relationship (SAR) generated in the studies is valuable for the design of novel chemotherapeutic agents.

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Synthesis, antiproliferative, acute toxicity and assessment of antiandrogenic activities of some newly synthesized steroidal lactams

Cited by 22 publications

References 42 publications

Nutritive Beeinflussung des Haarwachstums

Nutritive Beeinflussung des Haarwachstums

A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives

Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents

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