Novel synthesis of (24R,6E)-24-ethylcholest-6-hydroxyimino-4-en-3-one, a steroidal oxime fromCinachyrella spp. sponges

Kovganko, N. B.; Chernov, Yu. G.

doi:10.1007/bf02236428

Cited by 5 publications

(4 citation statements)

References 3 publications

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“…Seven steps were needed to synthesize compound 1 as reported in reference [4]. Later Kovganko et al reported two new synthesis routes for the compound 1, both were rather complicated and the overall yields were relatively low [9,10]. Here, we introduce a new synthetic method for the steroidal oxime compound 1, 2 and 4 with higher overall yields and fewer synthetic steps.…”

Section: Resultsmentioning

confidence: 99%

A facile and efficient synthesis of some (6E)-hydroximino-4-en-3-one steroids, steroidal oximes from Cinachyrella spp. sponges

Cui¹,

Huang²,

Fan³

et al. 2008

Steroids

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Using beta-sitosterol as a starting material, (6E)-hydroximino-24-ethylcholest-4-en-3-one (1), a natural steroidal oxime from Cinachyrella alloclada and C. apion, was synthesized in four steps with a high overall yield. First, beta-sitosterol (5a) is transformed into the corresponding 24-ethylcholest-4-en-3,6-dione (6a) via oxidation with pyridinium chlorochromate (PCC). Selective reduction of 6a by NaBH(4) in the presence of CoCl(2) gives 24-ethylcholest- 4-en-3beta-ol-6-one (7a). The reaction of 7a with hydroxylamine hydrochloride offers the oxime 8a and the oxidation of 8a by Jones reagent gives the target steroid 1. (6E)-Hydroximinocholest-4-en-3-one (2) and (6E)-hydroximino-24-ethylcholest-4,22-dien-3-one (4) were synthesized by a similar method. The cytotoxicity of the synthesized compounds against sk-Hep-1 (human liver carcinoma cell line), H-292 (human lung carcinoma cell line), PC-3 (human prostate carcinoma cell line) and Hey-1B (human ovarian carcinoma cell line) cells were investigated. The presence of a cholesterol-type side chain appears to be necessary for the biological activity.

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Section: Resultsmentioning

confidence: 99%

A facile and efficient synthesis of some (6E)-hydroximino-4-en-3-one steroids, steroidal oximes from Cinachyrella spp. sponges

Cui¹,

Huang²,

Fan³

et al. 2008

Steroids

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“…sponges, 362 was synthesized from β-sitosterol in 30% overall yield. 363 Six additional cytotoxic isomalabaricane derivatives, globstellatic acid E methyl ester 493, 3-O-acetyljaspiferal methyl esters B 494, D 495 and G 496 and the dimethyl esters of jaspiferoic acids A 497 and B 498, were obtained from a new species of Jaspis from Vanuatu, after methylation with diazo-methane to obtain the corresponding methyl esters. 364 Three additional isomalabaricanes, 29-hydroxystelliferin D 499, 3-epi-29-hydroxystelliferin E 500 and 3-epi-29-hydroxystelliferin A 501, that induce morphological changes in rat fibroblasts, were obtained from a Japanese specimen of Stelletta globostellata.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

2001

Nat. Prod. Rep.

398

128

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This review covers the marine natural products literature for the year 2000 and is organized phylogenetically, with sections on marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, coelenterates, bryozoans, molluscs, tunicates. echinoderms and miscellaneous marine organisms. There is an emphasis on new structures, stressing their biological activities, source organisms and countries of origin, and also syntheses that confirm the structures of known compounds. The review contains 869 structures and 592 references, of which 434 appeared between January and December 2000.

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“…The oxime function in the steroidal framework has been studied by several authors and first isolated from marine sponges [41,45]. In different reports, the (6 E )-hydroxyimino derivatives exhibited a selective cytotoxic activity against several types of cancer cells [46,47,48]. Furthermore, this group of steroids was also reported to show a high affinity for human placental aromatase and to function as a competitive inhibitor of this enzyme [48].…”

Section: Resultsmentioning

confidence: 99%

Antiproliferative, Cytotoxic, and Apoptotic Activity of Steroidal Oximes in Cervicouterine Cell Lines

et al. 2016

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Abstract:Steroidal sapogenins have shown antiproliferative effects against several tumor cell lines; and their effects on human cancer cells are currently under study. Changes in the functionality on the steroidal structure make it possible to modify the biological activity of compounds. Herein, we report the synthesis and in vitro antitumor activity of two steroidal oxime compounds on cervical cancer cells. These derivatives were synthesized from the steroidal sapogenin diosgenin in good yields. The in vitro assays show that the steroidal oximes show significant antiproliferative activity compared to the one observed for diosgenin. Cell proliferation, cell death, and the cytotoxic effects were determined in both cervical cancer cells and human lymphocytes. The cancer cells showed apoptotic morphology and an increased presence of active caspase-3, providing the notion of a death pathway in the cell. Significantly, the steroidal oximes did not exert a cytotoxic effect on lymphocytes.

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Novel synthesis of (24R,6E)-24-ethylcholest-6-hydroxyimino-4-en-3-one, a steroidal oxime fromCinachyrella spp. sponges

Cited by 5 publications

References 3 publications

A facile and efficient synthesis of some (6E)-hydroximino-4-en-3-one steroids, steroidal oximes from Cinachyrella spp. sponges

A facile and efficient synthesis of some (6E)-hydroximino-4-en-3-one steroids, steroidal oximes from Cinachyrella spp. sponges

Marine natural products

Antiproliferative, Cytotoxic, and Apoptotic Activity of Steroidal Oximes in Cervicouterine Cell Lines

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