1-chloromethyl-8,9-dihydro-7H-2,7,9a-triaza-benzo[cd]azulen-6-one | 433726-49-9

• 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: 1-chloromethyl-8,9-dihydro-7H-2,7,9a-triaza-benzo[cd]azulen-6-one
• 英文别名: 2-(Chloromethyl)-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one
• CAS: 433726-49-9
• 化学式: C₁₁H₁₀ClN₃O
• 分子量: 235.673
• InChiKey: ZIJHRWXWTYXUEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 1-chloromethyl-8,9-dihydro-7H-2,7,9a-triaza-benzo[cd]azulen-6-one 以 四氢呋喃 为溶剂， 反应 12.0h， 以74%的产率得到2-(Pyrrolidin-1-ylmethyl)-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one
  参考文献：
  名称：

  Design and synthesis of poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors. part 4: Biological evaluation of imidazobenzodiazepines as potent PARP-1 inhibitors for treatment of ischemic injuries

  摘要：

  A class of poly(ADP-ribose) polymerase (PARP-1) inhibitors, the imidazobenzodiazepines, are presented in this text. Several derivatives were designed and synthesized with ionizable groups (i.e., tertiary amines) in order to promote the desired pharmaceutical characteristics for administration in ischemic injury. Within this series, several compounds have excellent in vitro potency and our computational models accurately justify the structure-activity relationships (SARs) and highlight essential hydrogen bonding residues and hydrophobic pockets within the catalytic domain of PARP-1. Administration of these compounds (5q, 17a and 17e) in the mouse model of streptozotocin-induced diabetes results in maintainance of glucose levels. Furthermore, one such inhibitor (5g, IC50 = 26 nM) demonstrated significant reduction of infarct volume in the rat model of permanent focal cerebral ischemia. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00333-x
• 作为产物：
  描述：

  9-硝基-1,2,3,4-四氢-5H-1,4-苯并二氮杂卓-5-酮 在 palladium on activated charcoal 氯化亚砜 、 四丁基氟化铵 、 镍 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 生成 1-chloromethyl-8,9-dihydro-7H-2,7,9a-triaza-benzo[cd]azulen-6-one
  参考文献：
  名称：

  Design and synthesis of poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors. part 4: Biological evaluation of imidazobenzodiazepines as potent PARP-1 inhibitors for treatment of ischemic injuries

  摘要：

  A class of poly(ADP-ribose) polymerase (PARP-1) inhibitors, the imidazobenzodiazepines, are presented in this text. Several derivatives were designed and synthesized with ionizable groups (i.e., tertiary amines) in order to promote the desired pharmaceutical characteristics for administration in ischemic injury. Within this series, several compounds have excellent in vitro potency and our computational models accurately justify the structure-activity relationships (SARs) and highlight essential hydrogen bonding residues and hydrophobic pockets within the catalytic domain of PARP-1. Administration of these compounds (5q, 17a and 17e) in the mouse model of streptozotocin-induced diabetes results in maintainance of glucose levels. Furthermore, one such inhibitor (5g, IC50 = 26 nM) demonstrated significant reduction of infarct volume in the rat model of permanent focal cerebral ischemia. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00333-x

文献信息

• USE OF SUBSTITUTED BENZODIAZEPINONES AND BENZAZEPINONES OR THE SALTS THEREOF AS ACTIVE SUBSTANCES AGAINST ABIOTIC PLANT STRESS
  申请人：BAYER CROPSCIENCE AG

  公开号：US20150218110A1

  公开（公告）日：2015-08-06

  The use of substituted benzodiazepinones and benzazepinones of the general formula (I) or salts thereof where the radicals in the general formula (I) correspond to the definitions given in the description, for enhancing stress tolerance in plants to abiotic stress, for strengthening plant growth and/or for increasing plant yield, and to selected processes for preparing the compounds mentioned above.

  使用通式（I）或其盐的取代苯二氮平酮和苯并氮平酮，其中通式（I）中的基团对应于描述中给出的定义，用于增强植物对非生物胁迫的耐受性，加强植物生长和/或增加植物产量，并选择上述化合物的制备过程。
• VERWENDUNG SUBSTITUIERTER BENZODIAZEPINONE UND BENZAZEPINONE ODER DEREN SALZE ALS WIRKSTOFFE GEGEN ABIOTISCHEN PFLANZENSTRESS
  申请人：Bayer CropScience AG

  公开号：EP2892344A1

  公开（公告）日：2015-07-15
• US7235557B2
  申请人：——

  公开号：US7235557B2

  公开（公告）日：2007-06-26
• US7915280B2
  申请人：——

  公开号：US7915280B2

  公开（公告）日：2011-03-29
• USRE41150E1
  申请人：——

  公开号：USRE41150E1

  公开（公告）日：2010-02-23