(R)-2-methylpropane-2-sulfinic acid 1-[2-(2-benzyloxyethyl)-phenyl]meth-(E)-ylideneamide | 1123754-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-methylpropane-2-sulfinic acid 1-[2-(2-benzyloxyethyl)-phenyl]meth-(E)-ylideneamide
• 英文别名: (NE,R)-2-methyl-N-[[2-(2-phenylmethoxyethyl)phenyl]methylidene]propane-2-sulfinamide
• CAS: 1123754-52-8
• 化学式: C₂₀H₂₅NO₂S
• 分子量: 343.49
• InChiKey: HABHQBWIQDJJRK-INJUALFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Boc-3-溴吲哚 、 (R)-2-methylpropane-2-sulfinic acid 1-[2-(2-benzyloxyethyl)-phenyl]meth-(E)-ylideneamide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以47.5%的产率得到3-[(R)-[2-(2-benzyloxyethyl)phenyl]-((R)-2-methylpropane-2-sulfinylamino)methyl]indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Chiral IBR2 Analogues

  摘要：

  Two stereoselective routes were developed to synthesize optically pure IBR2 analogues 1-16. The first features addition of N-Boc-3-bromoindole 26 to the sulfinamide 25, providing a 1: 1 ratio of the separable diasteroisomers 27 and 28 in good yield. In a straightforward fashion, the sulfinamides 27 and 28 were conveniently converted into the key amines 39 and 47 over 8 steps, respectively, from which a series of 3,4-dihydroisoquinolinyl IBR2 analogues 1-14 containing fluorinated and trifluoromethylated benzyl groups were prepared. Another route highlights the highly enantioselective addition of indole to the sulfonyl amide 50 with bifunctional aminothioureas 57 and 58 as catalysts. After the reaction conditions were optimized, the desired sulfonyl amides (R)-55 and (S)-55 were obtained in 99% ee and 98% ee, respectively. Acylation of (R)-55 and (S)-55 separately and subsequent allylation gave compounds 60 and 63, respectively, which were further subjected to RCM to furnish compounds 61 and 64 and, after removal of the Boc groups, the desired IBR2 analogues 15 and 16.

  DOI：

  10.1021/jo802607f
• 作为产物：
  描述：

  2-<2-(Benzyloxy)ethyl>benzaldehyde 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以79%的产率得到(R)-2-methylpropane-2-sulfinic acid 1-[2-(2-benzyloxyethyl)-phenyl]meth-(E)-ylideneamide
  参考文献：
  名称：

  Stereoselective Synthesis of Chiral IBR2 Analogues

  摘要：

  Two stereoselective routes were developed to synthesize optically pure IBR2 analogues 1-16. The first features addition of N-Boc-3-bromoindole 26 to the sulfinamide 25, providing a 1: 1 ratio of the separable diasteroisomers 27 and 28 in good yield. In a straightforward fashion, the sulfinamides 27 and 28 were conveniently converted into the key amines 39 and 47 over 8 steps, respectively, from which a series of 3,4-dihydroisoquinolinyl IBR2 analogues 1-14 containing fluorinated and trifluoromethylated benzyl groups were prepared. Another route highlights the highly enantioselective addition of indole to the sulfonyl amide 50 with bifunctional aminothioureas 57 and 58 as catalysts. After the reaction conditions were optimized, the desired sulfonyl amides (R)-55 and (S)-55 were obtained in 99% ee and 98% ee, respectively. Acylation of (R)-55 and (S)-55 separately and subsequent allylation gave compounds 60 and 63, respectively, which were further subjected to RCM to furnish compounds 61 and 64 and, after removal of the Boc groups, the desired IBR2 analogues 15 and 16.

  DOI：

  10.1021/jo802607f

文献信息

• Novel RAD51 Inhibitors and Uses Thereof
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20180057483A1

  公开（公告）日：2018-03-01

  The present invention includes novel RAD51 inhibitors. The compounds of the invention may be useful in preventing or treating cancer in a subject in need thereof. The present invention also includes methods of preventing or treating cancer in a subject in need thereof by administering to the subject a therapeutically effective amount of a compound of the invention.

  本发明涵盖了新型RAD51抑制剂。本发明的化合物可能在预防或治疗需要的受试者中的癌症方面有用。本发明还涵盖了通过向受试者投予本发明化合物的治疗有效量来预防或治疗受试者中的癌症的方法。
• RAD51 inhibitors and uses thereof
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US10421753B2

  公开（公告）日：2019-09-24

  The present invention includes novel RAD51 inhibitors. The compounds of the invention may be useful in preventing or treating cancer in a subject in need thereof. The present invention also includes methods of preventing or treating cancer in a subject in need thereof by administering to the subject a therapeutically effective amount of a compound of the invention.

  本发明包括新型 RAD51 抑制剂。本发明的化合物可用于预防或治疗有需要的受试者的癌症。本发明还包括通过向有需要的受试者施用治疗有效量的本发明化合物来预防或治疗癌症的方法。
• Stereoselective Synthesis of Chiral IBR2 Analogues
  作者：Xiao-Long Qiu、Jiewen Zhu、Guikai Wu、Wen-Hwa Lee、A. Richard Chamberlin

  DOI：10.1021/jo802607f

  日期：2009.3.6

  Two stereoselective routes were developed to synthesize optically pure IBR2 analogues 1-16. The first features addition of N-Boc-3-bromoindole 26 to the sulfinamide 25, providing a 1: 1 ratio of the separable diasteroisomers 27 and 28 in good yield. In a straightforward fashion, the sulfinamides 27 and 28 were conveniently converted into the key amines 39 and 47 over 8 steps, respectively, from which a series of 3,4-dihydroisoquinolinyl IBR2 analogues 1-14 containing fluorinated and trifluoromethylated benzyl groups were prepared. Another route highlights the highly enantioselective addition of indole to the sulfonyl amide 50 with bifunctional aminothioureas 57 and 58 as catalysts. After the reaction conditions were optimized, the desired sulfonyl amides (R)-55 and (S)-55 were obtained in 99% ee and 98% ee, respectively. Acylation of (R)-55 and (S)-55 separately and subsequent allylation gave compounds 60 and 63, respectively, which were further subjected to RCM to furnish compounds 61 and 64 and, after removal of the Boc groups, the desired IBR2 analogues 15 and 16.