1H-pyrazole-N-propyl-1-carboxamidine hydrochloride

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1H-pyrazole-N-propyl-1-carboxamidine hydrochloride
• 英文别名: 1H-Pyrazole-N-propyl-1-carboxamide hydrochloride；N'-propyl-1H-pyrazol-2-ium-2-carboximidamide;chloride
• 化学式: C₇H₁₂N₄*ClH
• 分子量: 188.66
• InChiKey: SMTGBEIHRBSAIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N^α-Ac-3,4-didehydro-D,L-ornithine 、 1H-pyrazole-N-propyl-1-carboxamidine hydrochloride 在 sodium carbonate 作用下， 反应 144.0h， 以18%的产率得到(E)-2-Amino-5-(N'-propyl-guanidino)-pent-3-enoic acid
  参考文献：
  名称：

  Conformationally-restricted arginine analogues as alternative substrates and inhibitors of nitric oxide synthases

  摘要：

  Conformationally restricted arginine analogues (1-5) were synthesized and found to be alternative substrates or inhibitors of the three isozymes of nitric oxide synthase (NOS). A comparison of k(cat)/K-m values shows that (E)-3,4-didehydro-D,L-arginine(1) is a much better substrate than the corresponding (Z)-isomer (2) and 3-guanidino-D,L-phenylglycine (3), although none is as good a substrate as is arginine; 5-keto-D,L-arginine (4) is not a substrate, but is an inhibitor of the three isozymes. Therefore, it appears that arginine binds to all of the NOS isozymes in an extended (E-like) conformation. None of the compounds exhibits time-dependent inhibition of NOS, but they are competitive reversible inhibitors. Based on the earlier report that NW-propyl-L-arginine is a highly selective nNOS inhibitor (Zhang, H. Q.; Fast, W.; Marletta, M.; Martasek, P.; Silverman, R. B. J. Med. Chem. 1997, 40, 3869), (E)-N-omega-propyl-3,4-didehydro-D,L-arginine (5) was synthesized, but it was shown to be weakly potent and only a mildly selective inhibitor of NOS. Imposing conformational rigidity on an arginine backbone does not appear to be a favorable approach for selective NOS inhibition. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00029-2
• 作为产物：
  描述：

  吡唑 、 N-propylcyanamide 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 1H-pyrazole-N-propyl-1-carboxamidine hydrochloride
  参考文献：
  名称：

  1H-Pyrazole-1-carboxamidines: new inhibitors of nitric oxide synthase

  摘要：

  1H-Pyrazole-1-carboxamidines were prepared as potential inhibitors of the three isozymes of nitric oxide synthase. All of the compounds were found to be competitive inhibitors of all three isoforms. The most selective compound prepared was 1H-pyrazole-N-(3-aminomethylanilino)- 1-carboxamidine (14), which is 100-fold selective for nNOS over eNOS with a K-i value of 2 muM. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00573-4

文献信息

• [EN] IMIDAZO[4,5-c] RING COMPOUNDS CONTAINING SUBSTITUTED GUANIDINE GROUPS<br/>[FR] COMPOSÉS COMPRENANT UN CYCLE IMIDAZO[4,5-C] CONTENANT DES GROUPES GUANIDINE SUBSTITUÉS
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2017040234A1

  公开（公告）日：2017-03-09

  Imidazo[4,5-c] ring compounds, (particularly imidzao[4,5-c]quinolines, 6,7,8,9- tetrahydroimidazo[4,5-c]quinolines, imidazo[4,5-c]naphthyridines, and 6,7,8,9- tetrahydroimidazo[4,5-c]naphthyridine compounds) having a substituted guanidine substituent at the 1 -position, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed. Methods of use of the compounds as immune response modifiers, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are also disclosed.

  本发明涉及咪唑[4,5-c]环化合物，特别是咪唑[4,5-c]喹啉，6,7,8,9-四氢咪唑[4,5-c]喹啉，咪唑[4,5-c]萘啉和6,7,8,9-四氢咪唑[4,5-c]萘啉化合物，它们在1-位置具有取代的鸟氨酸取代基，以及含有这些化合物的药物组合物和制备这些化合物的方法。还公开了这些化合物作为免疫反应调节剂的使用方法，用于在动物中诱导细胞因子生物合成以及用于治疗包括病毒和肿瘤疾病在内的疾病的方法。
• Imidazo[4,5-c] ring compounds containing substituted guanidine groups
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US10118925B2

  公开（公告）日：2018-11-06

  Imidazo[4,5-c] ring compounds, (particularly imidzao[4,5-c]quinolines, 6,7,8,9-tetrahydroimidazo[4,5-c]quinolines, imidazo[4,5-c]naphthyridines, and 6,7,8,9-tetrahydroimidazo[4,5-c]naphthyridine compounds) having a substituted guanidine substituent at the 1-position, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed. Methods of use of the compounds as immune response modifiers, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are also disclosed.

  本发明公开了咪唑并[4,5-c]环化合物（特别是咪唑并[4,5-c]喹啉类、6,7,8,9-四氢咪唑并[4,5-c]喹啉类、咪唑并[4,5-c]萘啶类和 6,7,8,9-四氢咪唑并[4、5-c]萘啶化合物）、含有这些化合物的药物组合物以及制造这些化合物的方法。此外，还公开了将这些化合物用作免疫反应调节剂、诱导动物体内细胞因子的生物合成以及治疗包括病毒性和肿瘤性疾病在内的各种疾病的方法。
• Fused [1,2]imidazo[4,5-C] ring compounds substituted with guanidino groups
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US10414779B2

  公开（公告）日：2019-09-17

  Fused [1,2]Imidazo[4,5-c] ring compounds (e.g., imidzao[4,5-c]quinolines, 6,7,8,9-tetrahydroimidazo[4,5-c]quinolines, imidazo[4,5-c]naphthyridines, and 6,7,8,9-tetrahydroimidazo[4,5-c]naphthyridines) substituted on the fused ring with a group that contains a guanidine or substituted guanidine moiety, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed. Methods of use of the compounds as immune response modifiers, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are also disclosed.

  融合[1,2]咪唑并[4,5-c]环化合物（如公开了在融合环上被含有胍基或取代胍基的基团取代的咪唑并[4,5-c]喹啉类、6,7,8,9-四氢咪唑并[4,5-c]喹啉类、咪唑并[4,5-c]萘啶类和 6,7,8,9-四氢咪唑并[4,5-c]萘啶类化合物、含有这些化合物的药物组合物以及制造这些化合物的方法。还公开了将这些化合物用作免疫反应调节剂、诱导动物体内细胞因子的生物合成以及治疗包括病毒性和肿瘤性疾病在内的疾病的方法。
• Solid-Phase Syntheses of Nω-Propylarginine-Containing Dipeptides, Dipeptide Esters, and Dipeptide Amides
  作者：Younghee Lee

  DOI：10.1055/s-1999-6077

  日期：1999.8
• IMIDAZO[4,5-c]RING COMPOUNDS CONTAINING SUBSTITUTED GUANIDINE GROUPS
  申请人：3M Innovative Properties Company

  公开号：EP3344623A1

  公开（公告）日：2018-07-11