DDD-028 | 1538586-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: DDD-028
• 英文别名: 5-Methyl-1,5-diazapentacyclo[10.8.1.02,7.08,21.013,18]henicosa-2(7),8(21),9,11,13,15,17-heptaene；5-methyl-1,5-diazapentacyclo[10.8.1.02,7.08,21.013,18]henicosa-2(7),8(21),9,11,13,15,17-heptaene
• CAS: 1538586-09-2
• 化学式: C₂₀H₂₀N₂
• 分子量: 288.392
• InChiKey: XKGPHJMKJBEURD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  DDD-028 在 sodium cyanoborohydride 、 三氟乙酸 作用下， 反应 3.0h， 生成 (2R,7S)-5-methyl-1,5-diazapentacyclo[10.8.1.02,7.08,21.013,18]henicosa-8,10,12(21),13,15,17-hexaene 、 (2S,7R)-5-methyl-1,5-diazapentacyclo[10.8.1.02,7.08,21.013,18]henicosa-8,10,12(21),13,15,17-hexaene
  参考文献：
  名称：

  [EN] PENTACYCLIC PYRIDOINDOLOBENZ[b,d]AZEPINE DERIVATIVES AND USES THEREOF
  [FR] DÉRIVÉS DE PYRIDOINDOLOBENZ[B,D]AZÉPINES PENTACYCLIQUES ET LEURS UTILISATIONS

  摘要：

  本发明公开了式1的吡啶吲哌并苯[b,d]氮杂环化合物组合物，其中Y是单键或双键。A和B独立地为-(CH2)n-; 'n'的值在0至3之间变化。R1到R10是各种电子给予、电子提取、亲水性或亲脂性基团，选择这些基团以优化式I化合物的物理化学和生物学性质。

  公开号：

  WO2014137848A1
• 作为产物：
  描述：

  5,6-dihydro-7H-dibenzo[b,d]azepine 在 盐酸 、 对甲苯磺酸 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 、 甲苯 为溶剂， 反应 6.5h， 生成 DDD-028
  参考文献：
  名称：

  The synthesis and comparative receptor binding affinities of novel, isomeric pyridoindolobenzazepine scaffolds

  摘要：

  Compounds 7, 8, and 9, derived from the novel scaffolds 3, 5, and 6, were synthesized and evaluated in vitro. The b, c -> c,d shift of the E-phenyl ring resulted in a large decrease (ca. 20- to 1000-fold) in binding to the 5-HT2A, 5-HT2C and H-2, receptors, and a modest decrease (ca. 10- to 20-fold) in binding to the 5-HT5A, D-2, D-5, and alpha(1D), receptors. The b, c -> d, e shift resulted in a large decrease in binding to the 5-HT1D, 5-HT2C, 5-HT6, and H-1 receptors, a modest decrease in binding to 5-HT1A, 5-HT5A and D2, D5, alpha(2B), and H2 receptors, and a large increase in affinity to the 5-HT3, 5-HT6, and sigma(1) receptors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.024

文献信息

• [EN] PREVENTION AND TREATMENT OF NEURONAL DAMAGE WITH PYRIDOINDOLOBENZ[B, D] AZEPINE COMPOSITIONS<br/>[FR] PRÉVENTION ET TRAITEMENT D'UN DOMMAGE NEURONAL AVEC DES COMPOSITIONS DE PYRIDOINDOLOBENZ[B,D]AZÉPINE
  申请人：[en]DAYA DRUG DISCOVERIES, INC.

  公开号：WO2022265960A1

  公开（公告）日：2022-12-22

  A method of preventing or treating neuronal damage in a patient being administered a therapy that can cause nerve damage, comprising administering to said patient an effective amount of a neuroprotective compounds for Formula 1, (I) wherein Y is a single bond or a double bond; A and B are independently -(CH2)n-; subscript 'n' varies from 0 to 3.
• The synthesis and comparative receptor binding affinities of novel, isomeric pyridoindolobenzazepine scaffolds
  作者：Raghavan Rajagopalan、Acintya Bandyopadhyaya、Desikan R. Rajagopalan、Parthasarathi Rajagopalan

  DOI：10.1016/j.bmcl.2013.12.024

  日期：2014.1

  Compounds 7, 8, and 9, derived from the novel scaffolds 3, 5, and 6, were synthesized and evaluated in vitro. The b, c -> c,d shift of the E-phenyl ring resulted in a large decrease (ca. 20- to 1000-fold) in binding to the 5-HT2A, 5-HT2C and H-2, receptors, and a modest decrease (ca. 10- to 20-fold) in binding to the 5-HT5A, D-2, D-5, and alpha(1D), receptors. The b, c -> d, e shift resulted in a large decrease in binding to the 5-HT1D, 5-HT2C, 5-HT6, and H-1 receptors, a modest decrease in binding to 5-HT1A, 5-HT5A and D2, D5, alpha(2B), and H2 receptors, and a large increase in affinity to the 5-HT3, 5-HT6, and sigma(1) receptors. (C) 2013 Elsevier Ltd. All rights reserved.
• [EN] PENTACYCLIC PYRIDOINDOLOBENZ[b,d]AZEPINE DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS DE PYRIDOINDOLOBENZ[B,D]AZÉPINES PENTACYCLIQUES ET LEURS UTILISATIONS
  申请人：DAYA DRUG DISCOVERIES INC

  公开号：WO2014137848A1

  公开（公告）日：2014-09-12

  The present invention discloses pyridoindolobenz[b,d]azepines compositions of Formula 1, wherein Y is a single bond or a double bond. A and B are independently -(CH2)n-; and 'n' varies from 0 to 3. R1 to R10 are various electron donating, electron withdrawing, hydrophilic, or lipophilic groups selected to optimize the physicochemical and biological properties of compounds of Formula I.

  本发明公开了式1的吡啶吲哌并苯[b,d]氮杂环化合物组合物，其中Y是单键或双键。A和B独立地为-(CH2)n-; 'n'的值在0至3之间变化。R1到R10是各种电子给予、电子提取、亲水性或亲脂性基团，选择这些基团以优化式I化合物的物理化学和生物学性质。