4-(4-acetamido-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid | 225667-25-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(4-acetamido-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid
• 英文别名: 4-[(4-Acetamido-1-methylpyrrole-2-carbonyl)amino]-1-methylpyrrole-2-carboxylic acid
• CAS: 225667-25-4
• 化学式: C₁₄H₁₆N₄O₄
• 分子量: 304.305
• InChiKey: VQLSBSMSFTUPAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-acetamido-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid 在 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-[[4-[[4-(acetylamino)-1-methylpyrrol-2-yl]carbonylamino]-1-methylpyrrole-2-yl]carbonylamino]-1-methylpyrrole-2-carboxylic acid
  参考文献：
  名称：

  Ryabinin; Sinyakov, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 531 - 536

  摘要：

  DOI：
• 作为产物：
  描述：

  4-乙酰氨基-1-甲基吡咯-2-羧酸 在 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-(4-acetamido-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Ryabinin; Sinyakov, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 531 - 536

  摘要：

  DOI：

文献信息

• CC-1065 Analogues Bearing Different DNA-Binding Subunits:  Synthesis, Antitumor Activity, and Preliminary Toxicity Study
  作者：Yuqiang Wang、Lianfa Li、Wenqing Ye、Zhiming Tian、Wei Jiang、Hong Wang、Susan C. Wright、James W. Larrick

  DOI：10.1021/jm0203433

  日期：2003.2.1

  CC-1065 analogues bearing different DNA-binding subunits were synthesized. A terminal C5-NO2 and -F moiety at the DNA-binding subunit increased the drug's potency and antitumor efficacy. A C5-OCH3 reduced the potency and antitumor efficacy. Compound (+/-)-7, bearing a trans double bond, had increased antitumor efficacy. A preliminary toxicity study indicated that terminal C5-OCH3 and -acetamido moieties

  合成带有不同DNA结合亚基的CC-1065类似物。DNA结合亚基的末端C5-NO2和-F部分增加了药物的效力和抗肿瘤功效。C5-OCH3降低了效力和抗肿瘤功效。带有反式双键的化合物（+/-）-7具有增强的抗肿瘤功效。初步的毒性研究表明，DNA结合亚基的末端C5-OCH3和-乙酰氨基部分导致了小鼠的延迟死亡。
• Synthesis and DNA-cleaving activity of lactenediynes conjugated with DNA-complexing moieties
  作者：Luca Banfi、Andrea Basso、Elisabetta Bevilacqua、Valentina Gandolfo、Giuseppe Giannini、Giuseppe Guanti、Loana Musso、Monica Paravidino、Renata Riva

  DOI：10.1016/j.bmc.2008.02.022

  日期：2008.4.1

  Lactenediynes are compounds characterized by the fusion of a beta-lactam with a cyclodeca-3-ene-1,5-diyne. In this work the most promising members of this family have been activated by attaching a carbalkoxy or a carbamoyl group to the azetidinone nitrogen, and conjugated to various DNA-complexing moieties, either acting by intercalation or through groove binding. These conjugated artificial enediynes have been demonstrated to possess in vitro ability to produce single and double strand cleavage of plasmid DNA. As potency and capacity to induce double cut, they rank among the best simple enediyne analogues ever prepared. A thorough investigation was carried out in order to develop the best suited linkers for assembling these conjugates. (C) 2008 Elsevier Ltd. All rights reserved.
• Sequence-Specific DNA Alkylation by Hybrid Molecules between Segment A of Duocarmycin A and Pyrrole/Imidazole Diamide
  作者：Zhi-Fu Tao、Tsuyoshi Fujiwara、Isao Saito、Hiroshi Sugiyama

  DOI：10.1002/(sici)1521-3773(19990301)38:5<650::aid-anie650>3.0.co;2-o

  日期：1999.3.1

  In the absence of distamycin A (Dist), hybrids 1 (X=N, CH) selectively alkylate the 3' end of adenine in AT-rich DNA sequences. However, these hybrids can form a heterodimer with Dist to alkylate G residues of predetermined DNA sequences efficiently and with high selectivity.
• US7378237B2
  申请人：——

  公开号：US7378237B2

  公开（公告）日：2008-05-27