N-[(S)-1-phenylethyl]-1,2-benzenediamine | 407618-20-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[(S)-1-phenylethyl]-1,2-benzenediamine
• 英文别名: N1-[(1S)-1-phenylethyl]benzene-1,2-diamine；2-N-[(1S)-1-phenylethyl]benzene-1,2-diamine
• CAS: 407618-20-6
• 化学式: C₁₄H₁₆N₂
• 分子量: 212.294
• InChiKey: MQWPQVBEANBHRS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(S)-1-phenylethyl]-1,2-benzenediamine 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 8.42h， 生成 (1-[(S)-1-phenylethyl]-1H-benzimidazol-2-yl)-phenyl-methanone
  参考文献：
  名称：

  Aromatic Amination/Imination Approach to Chiral Benzimidazoles

  摘要：

  The powerful Buchwald-Hartwig amination was utilized for the construction of the benzimidazole nucleus with the substituted nitrogen atom bearing a chiral substituent. A successive amination/imination was followed by an acid-catalyzed ring closure step to give the benzimidazole ring. The products were deprotonated and acylated at the C2 position and could be alkylated on nitrogen to give chiral benzimidazolium salts.

  DOI：

  10.1021/jo016251n
• 作为产物：
  描述：

  (aS)-N-(2-溴苯基)-alpha-甲基-苯甲胺 在 tris(dibenzylideneacetone)dipalladium (0) 、 盐酸羟胺 、 sodium acetate 、 sodium t-butanolate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 1.5h， 生成 N-[(S)-1-phenylethyl]-1,2-benzenediamine
  参考文献：
  名称：

  Aromatic Amination/Imination Approach to Chiral Benzimidazoles

  摘要：

  The powerful Buchwald-Hartwig amination was utilized for the construction of the benzimidazole nucleus with the substituted nitrogen atom bearing a chiral substituent. A successive amination/imination was followed by an acid-catalyzed ring closure step to give the benzimidazole ring. The products were deprotonated and acylated at the C2 position and could be alkylated on nitrogen to give chiral benzimidazolium salts.

  DOI：

  10.1021/jo016251n

文献信息

• TRIAZOLOPYRAZINE
  申请人：ENGELHARDT Harald

  公开号：US20140142098A1

  公开（公告）日：2014-05-22

  Disclosed are compounds of the formula (I) wherein the groups R 1 to R 3 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.

  公开的是具有以下式（I）的化合物，其中基团R1至R3具有权利要求和说明书中给出的含义。本发明的化合物适用于治疗由细胞过度或异常增殖所特征化的疾病，包含这些化合物的制药制剂以及它们作为药物的用途。
• SUBSTITUTED [1,2,4]TRIAZOLO[4,3-a]PYRAZINES AS BRD4 INHIBITORS
  申请人：Boehringer Ingelheim International GmbH

  公开号：US20160129001A1

  公开（公告）日：2016-05-12

  Method for treating AML and MM by administration of a compound of the formula (I) wherein the groups R 1 to R 3 have the meanings given in the specification.

  使用化合物(I)治疗AML和MM的方法，其中R1至R3基团的含义如规范中所述。
• Substituted [1,2,4]triazolo[4,3-a]pyrazines as BRD4 inhibitors
  申请人：Boehringer Ingelheim International GmbH

  公开号：US10328074B2

  公开（公告）日：2019-06-25

  Method for treating AML and MM by administration of a compound of the formula (I) wherein the groups R1 to R3 have the meanings given in the specification.

  通过施用式 (I) 化合物治疗急性髓细胞白血病和 MM 的方法 其中基团 R1 至 R3 的含义见说明书。
• Triazolopyrazine
  申请人：Boehringer Ingelheim International GmbH

  公开号：US11077107B2

  公开（公告）日：2021-08-03

  Disclosed are compounds of the formula (I) wherein the groups R1 to R3 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.

  公开了式 (I) 的化合物 其中基团 R1 至 R3 具有权利要求和说明书中给出的含义。本发明的化合物适用于治疗以细胞过度增殖或异常增殖为特征的疾病，含有此类化合物的药物制剂及其作为药物的用途。
• Benzimidazole and imidazole inhibitors of histone deacetylases: Synthesis and biological activity
  作者：Jerome C. Bressi、Ron de Jong、Yiqin Wu、Andy J. Jennings、Jason W. Brown、Shawn O’Connell、Leslie W. Tari、Robert J. Skene、Phong Vu、Marc Navre、Xiaodong Cao、Anthony R. Gangloff

  DOI：10.1016/j.bmcl.2010.03.092

  日期：2010.5

  A series of N-hydroxy-3-[3-(1-substituted-1H-benzoimidazol-2-yl)-phenyl]-acrylamides (5a-5ab) and N-hydroxy-3-[ 3-( 1,4,5-trisubstituted-1H-imidazol-2-yl)-phenyl]-acrylamides (12a-s) were designed, synthesized, and found to be nanomolar inhibitors of human histone deacetylases. Multiple compounds bearing an N1-piperidine demonstrate EC(50)s of 20-100 nM in human A549, HL60, and PC3 cells, in vitro and in vivo hyperacetylation of histones H3 and H4, and induction of p21(waf). Compound 5x displays efficacy in human tumor xenograft models. (C) 2010 Elsevier Ltd. All rights reserved.