17-oximino-5-androsten-3β-yl phenoxyacetate | 1126086-40-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17-oximino-5-androsten-3β-yl phenoxyacetate
• 英文别名: 17-OXIMINO-5-ANDROSTEN-3beta-YL PHENOXYACETATE；[(3S,8R,9S,10R,13S,14S)-17-hydroxyimino-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] 2-phenoxyacetate
• CAS: 1126086-40-5
• 化学式: C₂₇H₃₅NO₄
• 分子量: 437.579
• InChiKey: KMFOEDVIXQJKLD-JJAANBCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  薯蓣皂素 在 甲醇 、 盐酸羟胺 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 17-oximino-5-androsten-3β-yl phenoxyacetate
  参考文献：
  名称：

  17-Oximino-5-androsten-3β-yl esters: synthesis, antiproliferative activity, acute toxicity, and effect on serum androgen level

  摘要：

  The 17-oximino-5-androsten-3 beta-yl esters (10a-10j) were synthesized from commercially available (25R)-5-Spirosten-3 beta-ol (Diosgenin) (4) as starting material. The synthesized compounds were evaluated for their antiproliferative activity against prostate specific cancer cell line DU-145, acute toxicity, and effect on serum androgen level and were compared with Finasteride used as positive control. Some of the compounds exhibited better cytotoxicity and antiandrogenic activity than the reference control. The detailed synthesis, spectroscopic data, and biological evaluation for the synthesized compounds are reported.

  DOI：

  10.1007/s00044-010-9393-3

文献信息

• NOVEL STEROIDAL ESTERS OF 17-OXIMINO-5-ANDROSTEN-3BETA-OL
  申请人：Bhardwaj Tilak Raj

  公开号：US20100292201A1

  公开（公告）日：2010-11-18

  The present invention relates to steroidal esters of 17-oximino-5-androsten-3-ol, of compound of general formula (A) wherein R is selected from a group consisting of arylalkyl, aryl, substituted aryl. The ester derivatives are synthesized starting from Dehydroandrosterone acetate. The compounds were tested for their antiproliferative activity and 5α-reductase inhibitory activity in comparison to Finasteride. Decreased androgen level have been found in serum of animal treated with newly synthesized compounds. These compounds have also shown better cytotoxicity in comparison to reference drug Finasteride. Thus such compounds can be useful in treatment of androgen dependent disorder of prostate alone or by synergistic effect they can decrease the size of prostate due to their antiproliferative activity.

  本发明涉及17-氧代氨基-5-雄烯-3-醇的类固醇酯化合物，通式（A）中R选自芳基烷基、芳基、取代芳基的群。酯衍生物是从去氢雄烯酮醋酸酯开始合成的。与非那雄胺相比，这些化合物被测试其抗增殖活性和5α-还原酶抑制活性。发现动物血清中的雄激素水平降低，这些动物接受了新合成化合物的治疗。与参考药物非那雄胺相比，这些化合物还表现出更好的细胞毒性。因此，这些化合物可以在治疗仅限于前列腺雄激素依赖性疾病中发挥作用，或者通过协同作用减小前列腺的大小，因为它们具有抗增殖活性。
• Steroidal esters of 17-oximino-5-androsten-3beta-ol
  申请人：Bhardwaj Tilak Raj

  公开号：US08435975B2

  公开（公告）日：2013-05-07

  The present invention relates to steroidal esters of 17-oximino-5-androsten-3-ol, of compound of general formula (A) wherein R is selected from a group consisting of arylalkyl, aryl, substituted aryl. The ester derivatives are synthesized starting from Dehydroandrosterone acetate. The compounds were tested for their antiproliferative activity and 5α-reductase inhibitory activity in comparison to Finasteride. Decreased androgen level have been found in serum of animal treated with newly synthesized compounds. These compounds have also shown better cytotoxicity in comparison to reference drug Finasteride. Thus such compounds can be useful in treatment of androgen dependent disorder of prostate alone or by synergistic effect they can decrease the size of prostate due to their antiproliferative activity.

  本发明涉及17-氧代氨基甾醇-5-烯-3-醇的类固醇酯类化合物，通式(A)中R选自苯基烷基、苯基、取代苯基等的群体中。酯类衍生物是从脱氢异雄甾酮醋酸酯开始合成的。与非那雄胺相比，这些化合物在抑制5α-还原酶活性和抗增殖活性方面进行了测试。治疗动物后，在其血清中发现了降低的雄激素水平。这些化合物在比较参考药物非那雄胺时，也显示出更好的细胞毒性。因此，这些化合物可以用于治疗前列腺的雄激素依赖性疾病，或者通过协同作用减小前列腺的大小，因为它们具有抗增殖活性。
• [EN] NOVEL STEROIDAL ESTERS OF 17-OXIMINO-5-ANDROSTEN-3ß-OL<br/>[FR] NOUVEAUX ESTERS STÉROÏDIENS DE 17-OXIMO-5-ANDROSTÈNE-3?-OL
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2009027994A4

  公开（公告）日：2009-06-25
• 17-Oximino-5-androsten-3β-yl esters: synthesis, antiproliferative activity, acute toxicity, and effect on serum androgen level
  作者：Neelima Dhingra、Tilak Raj Bhardwaj、Neeraj Mehta、Tapas Mukhopadhyay、Ashok Kumar、Manoj Kumar

  DOI：10.1007/s00044-010-9393-3

  日期：2011.9

  The 17-oximino-5-androsten-3 beta-yl esters (10a-10j) were synthesized from commercially available (25R)-5-Spirosten-3 beta-ol (Diosgenin) (4) as starting material. The synthesized compounds were evaluated for their antiproliferative activity against prostate specific cancer cell line DU-145, acute toxicity, and effect on serum androgen level and were compared with Finasteride used as positive control. Some of the compounds exhibited better cytotoxicity and antiandrogenic activity than the reference control. The detailed synthesis, spectroscopic data, and biological evaluation for the synthesized compounds are reported.