(2S)-1-(5-甲氧基-2-硝基-4-苯基甲氧基苯甲酰基)吡咯烷-2-羧酸 | 64154-79-6

• 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
• 中文名称: (2S)-1-(5-甲氧基-2-硝基-4-苯基甲氧基苯甲酰基)吡咯烷-2-羧酸
• 英文名称: (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxylic acid
• 英文别名: 1-[4-(Benzyloxy)-5-methoxy-2-nitrobenzoyl]-L-proline；(2S)-1-(5-methoxy-2-nitro-4-phenylmethoxybenzoyl)pyrrolidine-2-carboxylic acid
• CAS: 64154-79-6
• 化学式: C₂₀H₂₀N₂O₇
• 分子量: 400.388
• InChiKey: LAYKEZZQCFVAQQ-HNNXBMFYSA-N

物化性质

• 沸点：
  664.2±55.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-1-(5-甲氧基-2-硝基-4-苯基甲氧基苯甲酰基)吡咯烷-2-羧酸 在 三甲基氯硅烷 、 硫酸 、 三氟化硼乙醚 、 水 、 二异丁基氢化铝 、 potassium carbonate 、 乙硫醇 、 mercury dichloride 、 tin(ll) chloride 、 mercury(II) oxide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 2.0h， 生成 2-[5-[[(6aS)-2-methoxy-11-oxo-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]pentyl]benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Design and synthesis of C-8 linked pyrrolobenzodiazepine–naphthalimide hybrids as anti-tumour agents

  摘要：

  The facile synthesis of C-8 linked pyrrolobenzodiazepine-naphthalimide hybrid analogues is described. The compounds are prepared with varying degrees of linker length in order to probe the structural requirements for optimal in vitro anti-tumour activity. Some of these new hybrid compounds showed higher cytotoxic activity than the existing natural and synthetic pyrrolo[2,1-c][1,4]benzodiazepines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00326-8
• 作为产物：
  描述：

  香草酸 在 sodium hydroxide 、 氯化亚砜 、 硫酸 、 硝酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 生成 (2S)-1-(5-甲氧基-2-硝基-4-苯基甲氧基苯甲酰基)吡咯烷-2-羧酸
  参考文献：
  名称：

  Design and synthesis of C-8 linked pyrrolobenzodiazepine–naphthalimide hybrids as anti-tumour agents

  摘要：

  The facile synthesis of C-8 linked pyrrolobenzodiazepine-naphthalimide hybrid analogues is described. The compounds are prepared with varying degrees of linker length in order to probe the structural requirements for optimal in vitro anti-tumour activity. Some of these new hybrid compounds showed higher cytotoxic activity than the existing natural and synthetic pyrrolo[2,1-c][1,4]benzodiazepines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00326-8

文献信息

• New approaches to pyrrolo[2,1-c][1,4]benzodiazepines: synthesis, DNA-binding and cytotoxicity of DC-81
  作者：D. Subhas Bose、Gary B. Jones、David E. Thurston

  DOI：10.1016/s0040-4020(01)88134-5

  日期：——

  Two routes to the naturally occuring DNA-binding antitumor antibiotic DC-81 are described, one of which involves a novel cyclization process based on acid resin. The second route involves the synthesis of a new compound, 6-nitrovanillic acid, a key A-ring component of many naturally occuring PBDs. These routes have provided a sufficient quantity of DC-81 to allow complete characterization and evaluation

  描述了两种天然结合DNA的抗肿瘤抗生素DC-81的途径，其中一种涉及基于酸性树脂的新型环化过程。第二种途径涉及新化合物6-硝基香草酸的合成，6-硝基香草酸是许多天然存在的PBD的关键A环成分。这些途径提供了足够量的DC-81，可以在DNA结合和体外细胞毒性研究中进行完整的表征和评估。
• A new facile procedure for the preparation of pyrrolo[2,1-c][1,4]benzodiazepines: Synthesis of the antibiotic DC-81 and its thio analogue
  作者：Ahmed Kamal、B.S.Praveen Reddy、B.S.Narayan Reddy

  DOI：10.1016/0040-4039(96)00243-2

  日期：1996.3

  An efficient synthesis of the imine form of the pyrrolo[2,1-c][1,4]benzodiazepine ring system based on a new reductive cyclization procedure is described. The naturally occuring antibiotic DC-81(5c) and its 5-thio analogue (7c) have also been synthesized to illustrate the usefulness of this methodology.

  描述了一种基于新的还原环化程序的吡咯并[2,1- c ] [1,4]苯并二氮杂ring环系统的亚胺形式的有效合成。还合成了天然存在的抗生素DC-81（5c）及其5-硫代类似物（7c），以说明该方法的有用性。
• Enzymic approach to the synthesis of the pyrrolo[1,4]benzodiazepine antibiotics
  作者：Ahmed Kamal

  DOI：10.1021/jo00006a051

  日期：1991.3
• KAMAL, AHMED, J. ORG. CHEM., 56,(1991) N, C. 2237-2240
  作者：KAMAL, AHMED

  DOI：——

  日期：——
• Design and synthesis of C-8 linked pyrrolobenzodiazepine–naphthalimide hybrids as anti-tumour agents
  作者：Ahmed Kamal、B.S.Narayan Reddy、G.Suresh Kumar Reddy、G. Ramesh

  DOI：10.1016/s0960-894x(02)00326-8

  日期：2002.8

  The facile synthesis of C-8 linked pyrrolobenzodiazepine-naphthalimide hybrid analogues is described. The compounds are prepared with varying degrees of linker length in order to probe the structural requirements for optimal in vitro anti-tumour activity. Some of these new hybrid compounds showed higher cytotoxic activity than the existing natural and synthetic pyrrolo[2,1-c][1,4]benzodiazepines. (C) 2002 Elsevier Science Ltd. All rights reserved.