N-[5-({[3-(dimethylamino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-{[(4-{[imino(3-isoquinolinyl)methyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrole-2-carboxamide | 1000277-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-[5-({[3-(dimethylamino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-{[(4-{[imino(3-isoquinolinyl)methyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrole-2-carboxamide
• 英文别名: N-[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methyl-pyrrol-3-yl]carbamoyl]-1-methyl-pyrrol-3-yl]-4-(isoquinoline-3-carboximidoylamino)-1-methyl-pyrrole-2-carboxamide；N-[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-(isoquinoline-3-carboximidoylamino)-1-methylpyrrole-2-carboxamide
• CAS: 1000277-04-2
• 化学式: C₃₃H₃₈N₁₀O₃
• 分子量: 622.73
• InChiKey: IMMIFASXMYFHOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-甲基-4-硝基吡咯-2-羧酸 在 氯化亚砜 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 三甲胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 52.0h， 生成 N-[5-({[3-(dimethylamino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-{[(4-{[imino(3-isoquinolinyl)methyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  An evaluation of Minor Groove Binders as anti- Trypanosoma brucei brucei therapeutics

  摘要：

  A series of 32, structurally diverse MGBs, derived from the natural product distamycin, was evaluated for activity against Trypanosoma brucei brucei. Four compounds have been found to possess significant activity, in the nanomolar range, and represent hits for further optimisation towards novel treatments for Human and Animal African Trypanosomiases. Moreover, SAR indicates that the head group linking moiety is a significant modulator of biological activity. (C) 2016 The Authors. Published by Elsevier Masson SAS. This is an open access article under the CC BY license (http://creativecommons.orgilicensesiby/4.0/).

  DOI：

  10.1016/j.ejmech.2016.03.064

文献信息

• Antimicrobial Lexitropsins Containing Amide, Amidine, and Alkene Linking Groups
  作者：Nahoum G. Anthony、David Breen、Joanna Clarke、Gavin Donoghue、Allan J. Drummond、Elizabeth M. Ellis、Curtis G. Gemmell、Jean-Jacques Helesbeux、Iain S. Hunter、Abedawn I. Khalaf、Simon P. Mackay、John A. Parkinson、Colin J. Suckling、Roger D. Waigh

  DOI：10.1021/jm070831g

  日期：2007.11.1

  -resistant strains, in the range of 0.1-5 microg mL-1, which is comparable to many established antibacterial agents. Antifungal activity was also found in the range of 20-50 microg mL-1 MIC against Aspergillus niger and Candida albicans, again comparable with established antifungal drugs. A quinoline derivative was found to protect mice against S. aureus infection for a period of up to six days after a single

  描述了80种与二霉素和噻唑类相关的短小沟结合剂的合成和性能。化合物的设计主要基于小沟结合剂和DNA之间的疏水相互作用而增加的亲和力。疏水性芳族头基（包括喹啉基和苯甲酰基衍生物）的引入以及烯烃作为连接剂的引入，导致几种具有MIC的金黄色葡萄球菌的强活性抗菌化合物（对甲氧西林敏感和耐药的菌株）范围为0.1-5 microg mL -1，与许多已建立的抗菌剂相当。还发现针对黑曲霉和白色念珠菌的抗真菌活性为20-50微克mL-1 MIC，再次与已确立的抗真菌药物相当。
• An evaluation of Minor Groove Binders as anti- Trypanosoma brucei brucei therapeutics
  作者：Fraser J. Scott、Abedawn I. Khalaf、Federica Giordani、Pui Ee Wong、Sandra Duffy、Michael Barrett、Vicky M. Avery、Colin J. Suckling

  DOI：10.1016/j.ejmech.2016.03.064

  日期：2016.6

  A series of 32, structurally diverse MGBs, derived from the natural product distamycin, was evaluated for activity against Trypanosoma brucei brucei. Four compounds have been found to possess significant activity, in the nanomolar range, and represent hits for further optimisation towards novel treatments for Human and Animal African Trypanosomiases. Moreover, SAR indicates that the head group linking moiety is a significant modulator of biological activity. (C) 2016 The Authors. Published by Elsevier Masson SAS. This is an open access article under the CC BY license (http://creativecommons.orgilicensesiby/4.0/).