4-(4-formamido-1-methylpyrrole-2-carboxamido)-1-methylpyrrolecarboxylic acid | 183853-89-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(4-formamido-1-methylpyrrole-2-carboxamido)-1-methylpyrrolecarboxylic acid
• 英文别名: 4-[(4-Formamido-1-methylpyrrole-2-carbonyl)amino]-1-methylpyrrole-2-carboxylic acid
• CAS: 183853-89-6
• 化学式: C₁₃H₁₄N₄O₄
• 分子量: 290.279
• InChiKey: NALXBVXJLWYKHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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-formamido-1-methylpyrrole-2-carboxamido)-1-methylpyrrolecarboxylic acid 、 Acetic acid (S)-6-benzyloxy-2,3-dihydro-1H-indol-3-ylmethyl ester 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid (S)-6-benzyloxy-1-{4-[(4-formylamino-1-methyl-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carbonyl}-2,3-dihydro-1H-indol-3-ylmethyl ester
  参考文献：
  名称：

  Synthesis and evaluation of the hybrid molecules possessing DNA-cleaving activity

  摘要：

  The design and synthesis of enantiomerically enriched hybrid molecules, la-e and 2a-c, have been accomplished by employing the lipase-mediated asymmetric acetylation of prochiral diol 9 as the key step. Evaluation of their DNA-cleaving activity has revealed the unnatural type of enantiomer 2a-c to be more potent than la-e with natural configuration. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10030-0
• 作为产物：
  描述：

  Methyl 4-[(4-formamido-1-methylpyrrole-2-carbonyl)amino]-1-methylpyrrole-2-carboxylate 在 sodium hydroxide 作用下， 以50%的产率得到4-(4-formamido-1-methylpyrrole-2-carboxamido)-1-methylpyrrolecarboxylic acid
  参考文献：
  名称：

  N‐Formamido‐Containing Mono‐ and Diheterocyclic Pyrrole‐and Imidazole‐2‐carboxylic Acids as Building Blocks for Polyamide Synthesis

  摘要：

  Four N-formamido-containing mono-and diheterocyclic pyrrole- and imidazole-2-containing acids 1-4 were synthesized as intermediates for the preparation of polyamide molecules. The N-formamido-moiety forces the compounds to bind strongly as a stacked dimer, and in a staggered fashion, at specific sequences in the minor-groove of DNA. The acid moiety at the C-terminus of compounds enables these molecules to be coupled to amine-containing intermediates to form the amide linkages of the target polyamide. This convergent approach increases the synthetic diversity in polyamide chemistry by enabling one acid to be used with a variety of different C-terminus-functionalized intermediates.

  DOI：

  10.1080/00397910701648785

文献信息

• [EN] 5,7-DIAMINOPYRAZOLO`4,3-D!PYRIMIDINES USEFUL IN THE TREATMENT OF HYPERTENSION<br/>[FR] 5,7-DIAMINOPYRAZOLO`4,3-D!PYRIMIDINES UTILES POUR LE TRAITEMENT DE L'HYPERTENSION
  申请人：PFIZER LTD

  公开号：WO2004096810A1

  公开（公告）日：2004-11-11

  This invention relates to compounds of formula (I).

  这项发明涉及到式(I)的化合物。
• Synthesis of Fluoroquinolone-di- and tri-(N-methylpyrrole) Conjugates
  作者：Ichiro Suzuki、Mayuko Takahashi、Kei Takeda

  DOI：10.3987/com-10-12079

  日期：——

  Some FLQs, such as lomefloxacin and fleroxacin, having two fluorine atoms are known to generate an arylcarbene under photoirradiation conditions leading to DNA damage. We synthesized some conjugates between FLQs and di- and tri-(N-methylpyrrole) that are known as a DNA minor groove binder.
• Synthesis and biophysical evaluation of minor-groove binding C-terminus modified pyrrole and imidazole triamide analogs of distamycin
  作者：Toni Brown、Zarmeen Taherbhai、Jim Sexton、Arden Sutterfield、Mark Turlington、Justin Jones、Lindsay Stallings、Michelle Stewart、Karen Buchmueller、Hilary Mackay

  DOI：10.1016/j.bmc.2006.09.037

  日期：2007.1.1

  Five polyamide derivatives with rationally modified C-terminus moieties were synthesized and their DNA binding specificity and affinity determined. A convergent approach was employed to synthesize polyamides containing an alkylaminopiperazine (4 and 5), a truncated piperazine (6), or an alkyldiamino-C-terminus moiety (7 and 8) with two specific objectives: to investigate the effects of number of potential cationic centers and steric bulk at the C-terminus. CD studies confirmed that compounds 4, 5, 7, and 8 bind in the minor groove of DNA. The alkylpiperazine containing compounds (4 and 5) showed only moderate binding to DNA with AT values of 2.8 and 8.3 degrees C with their cognate sequence, respectively. The alkyldiamino compounds (7 and 8) were more impressive producing a Delta T-m of > 17 and > 22 degrees C, respectively. Compound 6 (truncated piperazine) did not stabilize its cognate DNA sequence. Footprints were observed for all compounds (except compound 6) with their cognate DNA sequence using DNase I footprinting, with compound 7 producing a footprint of 0.1 mu M at the expected 5'-ACGCGT-3' site. SPR analysis of compound 7 bindiy to 5'-ACGCGT-3', 5'-ACCGGT-3', and 5'-AAATTT-3' produced binding affinities of 2.2 x 10(6), 3.3 x 10(5), and 1 x 10(5) M-1, respectively, indicating a preference for its cognate sequence of 5'-ACGCGT-3'. These results are in good agreement with the footprinting data. The results indicate that steric crowding at the C-terminus is important with respect to binding. However, the number of cationic centers within the molecule may also play a role. The alkyldiamino-containing compounds (7 and 8) warrant further investigation in the field of polyamide research. (c) 2006 Elsevier Ltd. All rights reserved.
• NAPHTHALIMIDOBENZAMIDE DERIVATIVES
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：EP1020446B1

  公开（公告）日：2006-03-15
• 5,7-DIAMINOPYRAZOLO[4,3-D]PYRIMIDINES USEFUL IN THE TRAETMENT OF HYPERTENSION
  申请人：Pfizer Limited

  公开号：EP1620437A1

  公开（公告）日：2006-02-01