(S)-3-(benzyloxy)-2-methoxy-7,8,9,10-tetrahydrobenzo[e]pyrido[1,2-a][1,4]diazepin-12(6aH)-one | 1239587-66-6

• 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: (S)-3-(benzyloxy)-2-methoxy-7,8,9,10-tetrahydrobenzo[e]pyrido[1,2-a][1,4]diazepin-12(6aH)-one
• 英文别名: (6aS)-2-methoxy-3-phenylmethoxy-7,8,9,10-tetrahydro-6aH-pyrido[2,1-c][1,4]benzodiazepin-12-one
• CAS: 1239587-66-6
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: REDLRPJUAHJXHX-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(benzyloxy)-2-methoxy-7,8,9,10-tetrahydrobenzo[e]pyrido[1,2-a][1,4]diazepin-12(6aH)-one 在 CH2SO3H 、 二氯甲烷 、 Sodium sulfate-III 、 SiO2 、 methanol-dichloromethane 作用下， 以 二氯甲烷 、 碳酸氢钠 为溶剂， 反应 2.17h， 以to afford the title product (555 mg, 81% yield)的产率得到(S)-3-(hydroxy)-2-methoxy-7,8,9,10-tetrahydrobenzo[e]pyrido[1,2-a][1,4]diazepin-12(6aH)-one
  参考文献：
  名称：

  NOVEL CYTOTOXIC AGENTS FOR CONJUGATION TO A CELL BINDING MOLECULE

  摘要：

  本发明涉及一种新型细胞毒性剂，吡咯并[2,1-c][1,4]苯二氮平（PBD）衍生物，其与细胞结合剂的结合物，以及在靶向治疗癌症，自身免疫性疾病和传染病方面的制备和治疗用途。

  公开号：

  US20160207949A1
• 作为产物：
  描述：

  在 calcium carbonate 、 mercury dichloride 作用下， 以 水 、 乙腈 为溶剂， 反应 6.0h， 以32 mg的产率得到(S)-3-(benzyloxy)-2-methoxy-7,8,9,10-tetrahydrobenzo[e]pyrido[1,2-a][1,4]diazepin-12(6aH)-one
  参考文献：
  名称：

  Asymmetric syntheses of piperidino-benzodiazepines through ‘cation-pool’ host/guest supramolecular approach and their DNA-binding studies

  摘要：

  The asymmetric synthetic approach to piperidino-benzodiazepine 4a (a homolog of DC-81) has been developed The absolute stereochemistry of 4 and 5 has been assigned to be (S) at C-12a position This procedure features the use of a canon-pool strategy and also a host/guest supramolecular co-catalysis approach In this study the chloroformate of 8-phenylmenthyl has been employed as a chiral auxiliary and includes one-pot conditions for anodic oxidation which are followed by nucleophilic addition to an N-acyliminium ion In addition intramolecular azido reductive-cyclization and nitro reductive dithioacetal deprotective tandem-cyclization approaches have also been utilized for the syntheses of these compounds 4a b and 5a b Some of the representative compounds exhibited an enhanced DNA-binding ability in comparison to the natural product DC-81 (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.030

文献信息

• [EN] NOVEL CYTOTOXIC AGENTS FOR CONJUGATION OF DRUGS TO CELL BINDING MOLECULE<br/>[FR] NOUVEAUX AGENTS CYTOTOXIQUES POUR LA CONJUGAISON DE MÉDICAMENTS AVEC LA MOLÉCULE DE LIAISON CELLULAIRE
  申请人：HANGZHOU DAC BIOTECH CO LTD

  公开号：WO2015028850A1

  公开（公告）日：2015-03-05

  Provided are cytotoxic agents, pyrrolo[2,1-c][1,4]benzodiazepine (PBD) derivatives, their conjugates with a cell-binding agent, the preparation and the therapeutic uses in the targeted treatment of cancers, autoimmune disorders, and infectious diseases.

  提供了细胞毒性药物，吡咯并[2,1-c][1,4]苯二氮杂环己烷（PBD）衍生物，它们与细胞结合剂的结合物，以及在靶向治疗癌症、自身免疫性疾病和传染病中的制备和治疗用途。
• NOVEL CYTOTOXIC AGENTS FOR CONJUGATION OF DRUGS TO CELL BINDING MOLECULE
  申请人：Hangzhou Dac Biotech Co., Ltd

  公开号：EP3041846A1

  公开（公告）日：2016-07-13
• US9988408B2
  申请人：——

  公开号：US9988408B2

  公开（公告）日：2018-06-05
• Asymmetric syntheses of piperidino-benzodiazepines through ‘cation-pool’ host/guest supramolecular approach and their DNA-binding studies
  作者：Nagula Markandeya、Nagula Shankaraiah、Ch. Sanjeeva Reddy、Leonardo Silva Santos、Ahmed Kamal

  DOI：10.1016/j.tetasy.2010.10.030

  日期：2010.11

  The asymmetric synthetic approach to piperidino-benzodiazepine 4a (a homolog of DC-81) has been developed The absolute stereochemistry of 4 and 5 has been assigned to be (S) at C-12a position This procedure features the use of a canon-pool strategy and also a host/guest supramolecular co-catalysis approach In this study the chloroformate of 8-phenylmenthyl has been employed as a chiral auxiliary and includes one-pot conditions for anodic oxidation which are followed by nucleophilic addition to an N-acyliminium ion In addition intramolecular azido reductive-cyclization and nitro reductive dithioacetal deprotective tandem-cyclization approaches have also been utilized for the syntheses of these compounds 4a b and 5a b Some of the representative compounds exhibited an enhanced DNA-binding ability in comparison to the natural product DC-81 (C) 2010 Elsevier Ltd All rights reserved
• NOVEL CYTOTOXIC AGENTS FOR CONJUGATION TO A CELL BINDING MOLECULE
  申请人：HANGZHOU DAC BIOTECH CO., LTD

  公开号：US20160207949A1

  公开（公告）日：2016-07-21

  The present invention is related to novel cytotoxic agents, pyrrolo[2,1-c][1,4]benzodiazepine (PBD) derivatives, their conjugates with a cell-binding agent, the preparation and the therapeutic uses in the targeted treatment of cancers, autoimmune disorders, and infectious diseases.

  本发明涉及一种新型细胞毒性剂，吡咯并[2,1-c][1,4]苯二氮平（PBD）衍生物，其与细胞结合剂的结合物，以及在靶向治疗癌症，自身免疫性疾病和传染病方面的制备和治疗用途。