1H-Indole, 1-methyl-4-(2-nitroethenyl)- | 1829580-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1H-Indole, 1-methyl-4-(2-nitroethenyl)-
• 英文别名: 1-methyl-4-(2-nitroethenyl)indole
• CAS: 1829580-85-9
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: OXNWMYDXWIOWRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  48.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1H-Indole, 1-methyl-4-(2-nitroethenyl)- 在 吡啶 、 sodium tetrahydroborate 、 铁粉 、 氯化铵 作用下， 以 甲醇 、 水 、 异丙醇 、 乙腈 为溶剂， 反应 4.75h， 生成 4-bromo-N-[2-(1-methyl-1H-indol-4-yl)ethyl]benzenesulfonamide
  参考文献：
  名称：

  4-Indolyl- N -hydroxyphenylacrylamides as potent HDAC class I and IIB inhibitors in vitro and in vivo

  摘要：

  A series of 4,5-indolyl-N-hydroxyphenylacrylamides, as HDAC inhibitors, has been synthesized and evaluated in vitro and in vivo. 4-Indolyl compounds 13 and 17 functions as potent inhibitors of HDAC1 (IC50 1.28 nM and 134 nM) and HDAC 2 (IC50 0.90 and 0.53 nM). N-Hydroxy-3-{4-[2-(1H-indo1-4-y1)-ethylsulfamoyl]-phenyl}-actylamide (13) inhibited the human cancer cell growth of PC3, A549, MDA-MB-231 and AsPC-1 with a GI(50) of 0.14, 0.25, 0.32, and 0.24 mu M, respectively. In in vivo evaluations bearing prostate PC3 xenografts nude mice model, compound 13 suppressed tumor growth with a tumor growth inhibition (TGI) of 62.2%. Immunohistochemistry of protein expressions, in PC-3 xenograft model indicated elevated acetyl-histone 3 and prominently inhibited HDAC2 protein expressions. Therefore, compound 13 could be a suitable lead for further investigation and the development of selective HDAC 2 inhibitors as potent anti-cancer compounds. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.079
• 作为产物：
  描述：

  硝基甲烷 、 1-甲基-1H-吲哚-4-甲醛 在 ammonium acetate 作用下， 生成 1H-Indole, 1-methyl-4-(2-nitroethenyl)-
  参考文献：
  名称：

  4-Indolyl- N -hydroxyphenylacrylamides as potent HDAC class I and IIB inhibitors in vitro and in vivo

  摘要：

  A series of 4,5-indolyl-N-hydroxyphenylacrylamides, as HDAC inhibitors, has been synthesized and evaluated in vitro and in vivo. 4-Indolyl compounds 13 and 17 functions as potent inhibitors of HDAC1 (IC50 1.28 nM and 134 nM) and HDAC 2 (IC50 0.90 and 0.53 nM). N-Hydroxy-3-{4-[2-(1H-indo1-4-y1)-ethylsulfamoyl]-phenyl}-actylamide (13) inhibited the human cancer cell growth of PC3, A549, MDA-MB-231 and AsPC-1 with a GI(50) of 0.14, 0.25, 0.32, and 0.24 mu M, respectively. In in vivo evaluations bearing prostate PC3 xenografts nude mice model, compound 13 suppressed tumor growth with a tumor growth inhibition (TGI) of 62.2%. Immunohistochemistry of protein expressions, in PC-3 xenograft model indicated elevated acetyl-histone 3 and prominently inhibited HDAC2 protein expressions. Therefore, compound 13 could be a suitable lead for further investigation and the development of selective HDAC 2 inhibitors as potent anti-cancer compounds. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.079

文献信息

• Diastereodivergent Asymmetric Michael Addition of Cyclic Azomethine Ylides to Nitroalkenes: Direct Approach for the Synthesis of 1,7‐Diazaspiro[4.4]nonane Diastereoisomers
  作者：Chun‐Yan Li、Wu‐Lin Yang、Xiaoyan Luo、Wei‐Ping Deng

  DOI：10.1002/chem.201503729

  日期：2015.12.21

  diastereoselective and enantioselective catalytic asymmetric Michael addition of cyclic azomethine ylides with nitroalkenes have been developed to diastereodivergently generate either the syn or anti adducts by employing N,O‐ligand/Cu(OAc)2 and N,P‐ligand/Cu(OAc)2 catalytic systems. Both catalytic systems exhibit broad substrate applicability to afford the corresponding Michael adducts in good to excellent yields

  所述第一高度非对映选择性和对映选择性的催化不对称迈克尔加成与硝基烯烃环状甲亚胺叶立德的已发展到diastereodivergently产生任一顺式或反通过采用N，O-配体/铜（OAC）加合物2和N，P配体/铜（ OAc）2个催化系统。两种催化体系均显示出广泛的底物适用性，以良好至优异的收率提供相应的迈克尔加合物，具有极佳的非对映异构体水平（高达99：1非对映异构体比率）和对映选择性（高达> 99％对映异构体过量）。重要的是，通过简便的NaBH 4可以很容易地以高收率获得手性1,7-二氮杂螺[4.4]壬烷非对映异构体衍生物 减少迈克尔加合物。