(2'R)-2'-(methoxyphenyl)-4'-methylene-3-thioxospiro[androst-4-en-17,5'-[1,3,2]-oxathiaphospholane]-2'-sulfide | 1369486-71-4

• 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: (2'R)-2'-(methoxyphenyl)-4'-methylene-3-thioxospiro[androst-4-en-17,5'-[1,3,2]-oxathiaphospholane]-2'-sulfide
• 英文别名: (2R,5R,8'R,9'S,10'R,13'S,14'S)-2-(4-methoxyphenyl)-10',13'-dimethyl-4-methylidene-2-sulfanylidenespiro[1,3,2lambda5-oxathiaphospholane-5,17'-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-3'-thione；(2R,5R,8'R,9'S,10'R,13'S,14'S)-2-(4-methoxyphenyl)-10',13'-dimethyl-4-methylidene-2-sulfanylidenespiro[1,3,2λ5-oxathiaphospholane-5,17'-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-3'-thione
• CAS: 1369486-71-4
• 化学式: C₂₈H₃₅O₂PS₃
• 分子量: 530.756
• InChiKey: BUPCFKBWWRRBRQ-ICUMWPFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  劳森试剂 、 17Alpha-羟基黄体酮 以 甲苯 为溶剂， 反应 0.75h， 生成 (2'S)-2'-(methoxyphenyl)-4'-methylene-3-oxospiro[androst-4-en-17,5'-[1,3,2]-oxathiaphospholane]-2'-sulfide 、 (2'R)-2'-(methoxyphenyl)-4'-methylene-3-oxospiro[androst-4-en-17,5'-[1,3,2]-oxathiaphospholane]-2'-sulfide 、 (2'S)-2'-(methoxyphenyl)-4'-methylene-3-thioxospiro[androst-4-en-17,5'-[1,3,2]-oxathiaphospholane]-2'-sulfide 、 (2'R)-2'-(methoxyphenyl)-4'-methylene-3-thioxospiro[androst-4-en-17,5'-[1,3,2]-oxathiaphospholane]-2'-sulfide
  参考文献：
  名称：

  New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities

  摘要：

  The reactions of 17 alpha-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH2Cl2 and/or CCl4 gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D H-1-C-13 spectra (HSQC and HMBC) and homo-nuclear 2D spectra (NOESY) enabled complete H-1 and C-13 assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia sauna, were evaluated. All tested compounds showed strong antifungal activity. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.01.021

文献信息

• New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities
  作者：Natalija M. Krstić、Mira S. Bjelaković、Vladimir D. Pavlović、Koen Robeyns、Zorica D. Juranić、Ivana Matić、Irena Novaković、Dušan M. Sladić

  DOI：10.1016/j.steroids.2012.01.021

  日期：2012.4

  The reactions of 17 alpha-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH2Cl2 and/or CCl4 gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D H-1-C-13 spectra (HSQC and HMBC) and homo-nuclear 2D spectra (NOESY) enabled complete H-1 and C-13 assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia sauna, were evaluated. All tested compounds showed strong antifungal activity. (C) 2012 Elsevier Inc. All rights reserved.