(S)-3-hydroxy-2-methoxy-7,8,9,10-tetrahydrobenzo[e]pyrido[1,2-a][1,4]diazepin-6,12(5H,6aH)-dione | 1263193-97-0

• 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-hydroxy-2-methoxy-7,8,9,10-tetrahydrobenzo[e]pyrido[1,2-a][1,4]diazepin-6,12(5H,6aH)-dione
• 英文别名: (6aS)-3-hydroxy-2-methoxy-5,6a,7,8,9,10-hexahydropyrido[2,1-c][1,4]benzodiazepine-6,12-dione
• CAS: 1263193-97-0
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: IEIQYBATIXMXCE-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-methyl 1-(2-azido-4-hydroxy-5-methoxybenzoyl)piperidine-2-carboxylate 在 aluminium(III) triflate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以85%的产率得到(S)-3-hydroxy-2-methoxy-7,8,9,10-tetrahydrobenzo[e]pyrido[1,2-a][1,4]diazepin-6,12(5H,6aH)-dione
  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

• ASYMMETRIC CONJUGATE COMPOUNDS
  申请人：FEMTOGENIX LIMITED

  公开号：US20190144443A1

  公开（公告）日：2019-05-16

  The invention relates to compound of formula (I): A-X 1 -L-X 2 —B   (I) and salts, solvates and tautomers thereof, which are useful as medicaments, in particular as anti-proliferative agents and for use as a drug in an antibody-drug conjugate; wherein A is a group selected from: X 1 and X 2 are independently selected from O, S, NR 28 , CR 28 R 29 , CR 28 R 29 O, C(═O), C(═O)NR 28 , NR 28 C(═O), C(O)—R A —C(O)—NH, C(O)—R A —NH—C(O), C(O)—NH—R A —C(O), NH—C(O)—R A —C(O), NH—C(O)—R A —C(O)—NH, NH—C(O)—R A —NH—C(O), C(O)—NH—R A —NH—C(O), C(O)—NH—R A —C(O)—NH, O—C(O) and C(O)—O or is absent; L is selected from an amino acid, a peptide chain having from 2 to 12 amino acids, a paraformaldehyde chain —(OCH 2 ) 1-24 —, a polyethylene glycol chain —(OCH 2 CH 2 ) 1-12 — and —(CH 2 ) m —Y 6 —(CH 2 ) n — wherein Y 6 is selected from —(CH 2 ) z — and a group (L1) a group (L1) that is selected from arylene, monocyclic heteroarylene, monocyclic cycloalkylene, monocyclic cycloalkenylene and monocyclic heterocyclylene groups optionally substituted with up to three optional substituent groups; and B is a polycyclic group selected from: