7-iodo-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one | 1082051-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 7-iodo-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• 英文别名: 7-iodo-1-methyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one；7-iodo-1-methyl-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one；7-iodo-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
• CAS: 1082051-77-1
• 化学式: C₁₆H₁₃IN₂O
• 分子量: 376.197
• InChiKey: LPRQNTVANONHKM-UHFFFAOYSA-N

物化性质

• 熔点：
  86 °C
• 沸点：
  524.7±50.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-iodo-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 5-(1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-7-yl)pent-4-ynoic acid
  参考文献：
  名称：

  Design, synthesis and preliminary evaluation of a series of histone deacetylase inhibitors carrying a benzodiazepine ring

  摘要：

  A series of new histone deacetylase inhibitors were designed and synthesized based on hybridization between SAHA or oxamflatin and 5-phenyl-1,4-benzodiazepines. The compounds were tested for their enzyme inhibitory activity on HeLa nuclear extracts, and on human recombinant HDAC1 and HDAC6. Antiproliferative activity was tested on different cancer cells types, while proapoptotic activity was primarily tested on NB4 cells. The compounds showed IC50 values similar to those of SAHA. Compound (S)-8 displayed interesting activity against hematological and solid malignancies. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.017
• 作为产物：
  描述：

  (7-iodo-1-methyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one)(4'-methoxyphenyl)iodoniumtrifluoromethansulfonate 在 tetra-alkylammonium iodide 作用下， 以99%的产率得到7-iodo-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
  参考文献：
  名称：

  苯胺衍生的二芳基碘鎓盐的热解和放射性氟化†

  摘要：

  通过明智地利用吸电子保护基团，可以合成苯胺衍生的二芳基碘鎓盐并以良好至极好的收率进行官能化。这种简单的方法为在相对复杂的分子（如氟替莫尔）中对氨基芳烃进行放射性标记开辟了另一条途径。

  DOI：

  10.1039/c7ob00253j

文献信息

• [EN] 5-PHENYL-LH-BENZ0 [E] [1, 4] DIAZEPINE COMPOUNDS SUBSTITUTED WITH AN HYDROXAMIC ACID GROUP AS HISTONE DEACETYLASE INHIBITORS<br/>[FR] COMPOSÉS DE 5-PHÉNYL-LH-BENZO [E] [1, 4] DIAZÉPINE SUBSTITUÉS AVEC UN GROUPE D'ACIDE HYDROXAMIQUE EN TANT QU'INHIBITEURS D'HISTONE DÉACÉTYLASE
  申请人：UNIV FIRENZE

  公开号：WO2009081349A1

  公开（公告）日：2009-07-02

  Novel hydroxamate histone deacetylase inhibitors of formula (I) wherein X is C=O or CH2 used as antineoplastic agent.

  新型羟肟酸组蛋白去乙酰化酶抑制剂的化学式(I)，其中X为C=O或CH2，用作抗肿瘤药物。
• Design, synthesis and preliminary biological evaluation of new hydroxamate histone deacetylase inhibitors as potential antileukemic agents
  作者：L. Guandalini、C. Cellai、A. Laurenzana、S. Scapecchi、F. Paoletti、M.N. Romanelli

  DOI：10.1016/j.bmcl.2008.07.119

  日期：2008.9

  concerns the synthesis of new histone deacetylase inhibitors (HDACi) characterized by a 1,4-benzodiazepine ring used as the cap, joined through an amide function or a triple bond as connection units, to a linear alkyl chain bearing the hydroxamate function as Zn2+-chelating group. Biological tests performed in human acute promyelocytic leukemia NB4 cells showed that new hybrids can induce histone H3/H4

  这项研究涉及新的组蛋白脱乙酰基酶抑制剂（HDACi）的合成，其特征是将1,4-苯并二氮杂环用作帽，通过酰胺功能或三键作为连接单元连接到带有异羟肟酸酯功能的线性烷基链上。 Zn2 +-螯合基团。在人类急性早幼粒细胞白血病NB4细胞中进行的生物学测试表明，新的杂种可以诱导组蛋白H3 / H4乙酰化，生长停滞以及细胞凋亡。值得注意的是，手性化合物表现出立体选择性活性。
• 5-PHENYL-LH-BENZ0 [E] [1,4] DIAZEPINE COMPOUNDS SUBSTITUTED WITH AN HYDROXAMIC ACID GROUP AS HISTONE DEACETYLASE INHIBITORS
  申请人：Paoletti Francesco

  公开号：US20100331316A1

  公开（公告）日：2010-12-30

  Novel hydroxamate histone deacetylase inhibitors of formula (I) wherein X is C═O or CH 2 used as antineoplastic agent.

  化合物(I)是一种新型的羟酰胺组蛋白去乙酰化酶抑制剂，其中X为C═O或CH2，可作为抗肿瘤药物。
• 5-PHENYL-LH-BENZ0 [E] [1, 4] DIAZEPINE COMPOUNDS SUBSTITUTED WITH AN HYDROXAMIC ACID GROUP AS HISTONE DEACETYLASE INHIBITORS
  申请人：Universita' Degli Studi di Firenze

  公开号：EP2231623A1

  公开（公告）日：2010-09-29
• 5-PHENYL-1H-BENZO[E][1, 4]DIAZEPINE COMPOUNDS SUBSTITUTED WITH AN HYDROXAMIC ACID GROUP AS HISTONE DEACETYLASE INHIBITORS
  申请人：Universita' Degli Studi di Firenze

  公开号：EP2231623B1

  公开（公告）日：2013-05-22