2-[(2S)-9-(4-hydroxybenzyl)-2-((1S)-1-methylpropyl)-7-nitro-3-oxo-1,2,4,5-tetrahydrobenzo[1,4]diazepin-4-yl]acetic acid | 914301-54-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(2S)-9-(4-hydroxybenzyl)-2-((1S)-1-methylpropyl)-7-nitro-3-oxo-1,2,4,5-tetrahydrobenzo[1,4]diazepin-4-yl]acetic acid
• 英文别名: 2-[(2S)-2-[(2S)-butan-2-yl]-9-[(4-hydroxyphenyl)methyl]-7-nitro-3-oxo-2,5-dihydro-1H-1,4-benzodiazepin-4-yl]acetic acid
• CAS: 914301-54-5
• 化学式: C₂₂H₂₅N₃O₆
• 分子量: 427.457
• InChiKey: VMDHJQMDIWYFOR-RBZFPXEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(2S)-9-(4-hydroxybenzyl)-2-((1S)-1-methylpropyl)-7-nitro-3-oxo-1,2,4,5-tetrahydrobenzo[1,4]diazepin-4-yl]acetic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 [(S)-7-Amino-9-(4-tert-butoxycarbonyloxy-benzyl)-2-((S)-sec-butyl)-3-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-acetic acid
  参考文献：
  名称：

  Design, Synthesis, and Incorporation of a β-Turn Mimetic in Angiotensin II Forming Novel Pseudopeptides with Affinity for AT₁ and AT₂ Receptors

  摘要：

  A benzodiazepine-based beta-turn mimetic has been designed, synthesized, and incorporated into angiotensin II. Comparison of the mimetic with beta-turns in crystallized proteins showed that it most closely resembles a type II beta-turn. The compounds exhibited high to moderate binding affinity for the AT(2) receptor, and one also displayed high affinity for the AT(1) receptor. Molecular modeling showed that the high-affinity compounds could be incorporated into a previously derived model of AT(2) receptor ligands.

  DOI：

  10.1021/jm051222g
• 作为产物：
  描述：

  [(S)-2-((S)-sec-Butyl)-9-(4-methoxy-benzyl)-7-nitro-3-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-acetaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 三氟二甲基硫醚络合物 、 环己烯 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 2.0h， 生成 2-[(2S)-9-(4-hydroxybenzyl)-2-((1S)-1-methylpropyl)-7-nitro-3-oxo-1,2,4,5-tetrahydrobenzo[1,4]diazepin-4-yl]acetic acid
  参考文献：
  名称：

  Design, Synthesis, and Incorporation of a β-Turn Mimetic in Angiotensin II Forming Novel Pseudopeptides with Affinity for AT₁ and AT₂ Receptors

  摘要：

  A benzodiazepine-based beta-turn mimetic has been designed, synthesized, and incorporated into angiotensin II. Comparison of the mimetic with beta-turns in crystallized proteins showed that it most closely resembles a type II beta-turn. The compounds exhibited high to moderate binding affinity for the AT(2) receptor, and one also displayed high affinity for the AT(1) receptor. Molecular modeling showed that the high-affinity compounds could be incorporated into a previously derived model of AT(2) receptor ligands.

  DOI：

  10.1021/jm051222g