5-(aminomethyl)-1-methylpyrrole-2-carbonitrile | 203792-37-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(aminomethyl)-1-methylpyrrole-2-carbonitrile
• 英文别名: 5-(Aminomethyl)-1-methyl-1H-pyrrole-2-carbonitrile
• CAS: 203792-37-4
• 化学式: C₇H₉N₃
• mdl: MFCD12923552
• 分子量: 135.169
• InChiKey: WUKFHFANYNSORE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(aminomethyl)-1-methylpyrrole-2-carbonitrile 在 镍 N-甲基吗啉 、 盐酸 、 O-[(ethoxycarbonyl)cyanomethyleneamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 盐酸羟胺 、 氢气 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 ((R)-2-{(S)-2-[(5-Carbamimidoyl-1-methyl-1H-pyrrol-2-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic acid; compound with GENERIC INORGANIC NEUTRAL COMPONENT
  参考文献：
  名称：

  d-Phe-Pro-Arg type thrombin inhibitors: unexpected selectivity by modification of the P1 moiety

  摘要：

  Synthesis of thrombin inhibitors and their binding mode to thrombin is described. Modification of the P1 moiety leads to an increased selectivity versus trypsin. The observed selectivity is discussed in view of their thrombin-inhibitor complex X-ray structures.

  DOI：

  10.1016/s0960-894x(03)00347-0
• 作为产物：
  描述：

  N-甲基-2-吡咯腈 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium azide 、 四溴化碳 、 氢气 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 5-(aminomethyl)-1-methylpyrrole-2-carbonitrile
  参考文献：
  名称：

  d-Phe-Pro-Arg type thrombin inhibitors: unexpected selectivity by modification of the P1 moiety

  摘要：

  Synthesis of thrombin inhibitors and their binding mode to thrombin is described. Modification of the P1 moiety leads to an increased selectivity versus trypsin. The observed selectivity is discussed in view of their thrombin-inhibitor complex X-ray structures.

  DOI：

  10.1016/s0960-894x(03)00347-0

文献信息

• Thrombin inhibitors
  申请人：Abbott GmbH & Co., KG

  公开号：US06740647B1

  公开（公告）日：2004-05-25

  Novel five-membered heterocyclic amidines, their preparation and use as competitive inhibitors of trypsin-like serine proteases, especially thrombin and kininogenases such as kallikrein. Pharmaceutical compositions which contain the compounds as active ingredients, and use of the compounds as thrombin inhibitors, anticoagulants and antiinflammatory agents.

  新型五元杂环胺基化物，其制备和用作胰蛋白酶样丝氨酸蛋白酶的竞争性抑制剂，特别是血栓素和激肽原酶如激肽原酶的抑制剂。含有这些化合物作为活性成分的药物组合物，以及将这些化合物用作血栓素抑制剂、抗凝剂和抗炎药剂。
• [EN] THROMBIN INHIBITORS<br/>[FR] INHIBITEURS DE THROMBINE
  申请人：LG CHEMICAL LTD

  公开号：WO2000039124A1

  公开（公告）日：2000-07-06

  The present invention relates to thrombin inhibitors of formula (I), wherein A, B, C, D, E, F and n have the meaning given in the description, that are useful as anticoagulants. In particular, this invention relates to peptide derivatives having high antithrombotic activity and high oral bioavailability.

  本发明涉及式(I)的凝血酶抑制剂，其中A、B、C、D、E、F和n具有描述中给定的含义，可用作抗凝剂。特别是，本发明涉及具有高抗血栓活性和高口服生物利用度的肽衍生物。
• THROMBIN INHIBITORS
  申请人：LG Life Sciences Ltd.

  公开号：EP1140918B1

  公开（公告）日：2004-08-11
• Orally active thrombin inhibitors. Part 1: Optimization of the P1-moiety
  作者：Helmut Mack、Dorit Baucke、Wilfried Hornberger、Udo E.W. Lange、Werner Seitz、H. Wolfgang Höffken

  DOI：10.1016/j.bmcl.2006.02.040

  日期：2006.5

  The synthesis and SAR of novel nanomolar thrombin inhibitors with the common backbone HOOC-CH2-D-cyclohexylalanyl-3,.4-dehydroprolyl-NH-CH2-aryl-C(=NH)NH2 are described together with their ecarin clotting time (ECT) prolongation as measure for thrombin inhibition ex vivo. The aryl P1-moiety mimicking the arginine part of the D-Phe-Pro-Arg derived thrombin inhibitors turned out to be a key component for in vitro potency and in vivo activity. Optimization of this part led to compounds with improved antithrombin activity in rats and dogs after oral administration compared to the recently launched anticoagulant melagatran. (C) 2006 Elsevier Ltd. All rights reserved.
• THROMBININHIBITOREN
  申请人：Abbott GmbH & Co. KG

  公开号：EP0956294B1

  公开（公告）日：2004-06-09