17-oxa-D-homo-1,4,6-androstatrien-3,16-dione | 849425-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 17-oxa-D-homo-1,4,6-androstatrien-3,16-dione
• 英文别名: (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-4,4a,4b,10b,11,12-hexahydro-1H-naphtho[2,1-f]isochromene-3,8-dione
• CAS: 849425-41-8
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: IDEXTUTWDFJTTI-AKKLJKOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17-oxa-D-homo-1,4,6-androstatrien-3,16-dione 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以10%的产率得到1α,2α-epoxy-17-oxa-D-homoandrosta-4,6-diene-3,16-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of some new A,B-ring modified steroidal d-lactones

  摘要：

  Starting from the D-homo lactones of androst-4-en-3-one 3 and 4, prepared from 1 and 2, the new 17a homolactones 5-12, 14 and 15, were synthesized. The 4-hydroxy compounds 9 and 10 were obtained through the reaction of 4 alpha,5 alpha- (5 and 7) and 4 beta,5 beta- (6 and 8) epoxides with formic acid. The epoxides 5 and 6 were prepared from compound 3, and epoxides 7 and 8 from compound 4 by oxidation with H(2)O(2) under basic conditions. Compound I served as a starting substance for obtaining lactones 11-13. Oxidation of compound 1 with m-chloroperbenzoic acid yielded 11 and 12, but compound 13 gave 14. Compound 15 was obtained from 13 by oxidation with H(2)O(2) under basic conditions. The structures of epoxides 6 and 14 were confirmed by X-ray structural analysis. Cytotoxic activity against three tumor cell lines (human breast adenocarcinoma ER+, MCF-7, human breast adenocarcinoma ER-, MDA-MB-231, and prostate cancer PC3) was evaluated. Compounds 6 and 14 showed strong activity against PC3, the IC(50) being 10.6 and 2.2 mu M, respectively, whereas compounds 3 and 8 showed strong activity against MDA-MB-231 (IC(50) is 9.3 and 3.6 mu M, respectively). Aromatase inhibition assay showed that the tested compounds 9, 10, and 14 possess lower activity compared to formestane. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.02.006
• 作为产物：
  描述：

  3β-hydroxy-17-oxa-17a-homoandrost-5-en-16-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以43%的产率得到17-oxa-D-homo-1,4,6-androstatrien-3,16-dione
  参考文献：
  名称：

  Synthesis and anti-aromatase activity of some new steroidal D-lactones

  摘要：

  Starting from D-seco derivatives of 5-androstene 1-3, the D-homo lactones, 4 and 5, were synthesized. By the Oppenauer oxidation and/or by dehydration of 4 and 5 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or 2,3,5,6-tetrachloro-1,4-betizoquinone (chloranil), the corresponding D-lactones 6-12 were obtained. The structures of 6 and 10 were unambiguously proved by the appropriate X-ray structural analysis. Anti-aromatase assay showed that tested compounds possess inhibition potency, however. two to four times smaller (IC50 from 0.2 to 0.7 mum, respectively) in comparison to aminoglutethimide (AG). (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.10.005

文献信息

• Synthesis and biological evaluation of some new A,B-ring modified steroidal d-lactones
  作者：Evgenija A. Djurendić、Marija N. Sakač、Marina P. Zaviš、Andrea R. Gaković、Janoš J. Čanadi、Silvana A. Andrić、Olivera R. Klisurić、Vesna V. Kojić、Gordana M. Bogdanović、Katarina M. Penov Gaši

  DOI：10.1016/j.steroids.2008.02.006

  日期：2008.7

  Starting from the D-homo lactones of androst-4-en-3-one 3 and 4, prepared from 1 and 2, the new 17a homolactones 5-12, 14 and 15, were synthesized. The 4-hydroxy compounds 9 and 10 were obtained through the reaction of 4 alpha,5 alpha- (5 and 7) and 4 beta,5 beta- (6 and 8) epoxides with formic acid. The epoxides 5 and 6 were prepared from compound 3, and epoxides 7 and 8 from compound 4 by oxidation with H(2)O(2) under basic conditions. Compound I served as a starting substance for obtaining lactones 11-13. Oxidation of compound 1 with m-chloroperbenzoic acid yielded 11 and 12, but compound 13 gave 14. Compound 15 was obtained from 13 by oxidation with H(2)O(2) under basic conditions. The structures of epoxides 6 and 14 were confirmed by X-ray structural analysis. Cytotoxic activity against three tumor cell lines (human breast adenocarcinoma ER+, MCF-7, human breast adenocarcinoma ER-, MDA-MB-231, and prostate cancer PC3) was evaluated. Compounds 6 and 14 showed strong activity against PC3, the IC(50) being 10.6 and 2.2 mu M, respectively, whereas compounds 3 and 8 showed strong activity against MDA-MB-231 (IC(50) is 9.3 and 3.6 mu M, respectively). Aromatase inhibition assay showed that the tested compounds 9, 10, and 14 possess lower activity compared to formestane. (C) 2008 Elsevier Inc. All rights reserved.
• Synthesis and anti-aromatase activity of some new steroidal D-lactones
  作者：Katarina M. Penov Gaši、Srdjan Z. Stojanović、Marija N. Sakač、Mirjana Popsavin、Suzana Jovanović Šanta、Slobodanka M. Stanković、Olivera R. Klisurić、Nebojša Andrić、Radmila Kovačević

  DOI：10.1016/j.steroids.2004.10.005

  日期：2005.1

  Starting from D-seco derivatives of 5-androstene 1-3, the D-homo lactones, 4 and 5, were synthesized. By the Oppenauer oxidation and/or by dehydration of 4 and 5 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or 2,3,5,6-tetrachloro-1,4-betizoquinone (chloranil), the corresponding D-lactones 6-12 were obtained. The structures of 6 and 10 were unambiguously proved by the appropriate X-ray structural analysis. Anti-aromatase assay showed that tested compounds possess inhibition potency, however. two to four times smaller (IC50 from 0.2 to 0.7 mum, respectively) in comparison to aminoglutethimide (AG). (C) 2004 Elsevier Inc. All rights reserved.