5-aminopyridine-2-carboximidamide hydrochloride | 1258290-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-aminopyridine-2-carboximidamide hydrochloride
• 英文别名: 2-amidino-5-aminopyridine hydrochloride；4-aminopicolinimidamide hydrochloride；5-amino-2-amidinopyridine hydrochloride；5-Aminopyridine-2-carboximidamide hydrochloride；5-aminopyridine-2-carboximidamide;hydrochloride
• CAS: 1258290-09-3
• 化学式: C₆H₈N₄*ClH
• mdl: MFCD24842890
• 分子量: 172.617
• InChiKey: HTILMVXEHVZPSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.77
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.8
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-aminopyridine-2-carboximidamide hydrochloride 、 邻苯二甲醛 以 乙醇 为溶剂， 反应 4.0h， 以41%的产率得到6-amidino-N-[2-(6-amidinopyridin-3-yl)isoindolin-1-ylidene]pyridin-3-amine dihydrochloride
  参考文献：
  名称：

  Novel phenyl and pyridyl substituted derivatives of isoindolines: Synthesis, antitumor activity and DNA binding features

  摘要：

  Novel phenyl-substituted (3a-3d, 4a, 5, 8a, 8b and 9a) and pyridyl-substituted (3e-3i, 4b, 8c-8e, 9b and 9c) isoindolines were prepared in the reaction of o-phthalaldehyde and corresponding substituted aromatic and heteroaromatic amines by modification of reaction conditions from low to high temperature and from neutral to acidic environment.The antiproliferative activity of chosen substituted isoindolines was assessed on a panel of tumour cell lines and normal human fibroblasts. The majority of tested compounds was active at the highest tested concentrations phenyl-substituted isoindolines 3a and 3b and pyridyl-substituted isoindoline 3g showed a selective effect at micromolar concentrations on HepG2 cell line in comparison with other tested tumour cell lines and normal human fibroblasts. The strongest yet non-selective effect was observed for the pyridyl-substituted isoindoline 8c. These isoindoline derivatives showed diverse mechanism of action on tumour cell death induction as compounds 3a and Sc probably induced mitotic catastrophe while compound 3b induced apoptosis. Indeed. DNA binding properties evidenced that compounds 8a, 8c and 8d bind to DNA as highly potent DNA intercalators. By contrast, compounds 3b, 3e, 3i, 4a and 5 did not target the DNA. At last, the phenyl-substituted compound 8b proved to be a strong DNA binding compound with sequence selective binding and without DNA intercalation profile. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.079
• 作为产物：
  描述：

  3-氨基-6-氰基吡啶 在 盐酸 、 氨 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 5-aminopyridine-2-carboximidamide hydrochloride
  参考文献：
  名称：

  Novel phenyl and pyridyl substituted derivatives of isoindolines: Synthesis, antitumor activity and DNA binding features

  摘要：

  Novel phenyl-substituted (3a-3d, 4a, 5, 8a, 8b and 9a) and pyridyl-substituted (3e-3i, 4b, 8c-8e, 9b and 9c) isoindolines were prepared in the reaction of o-phthalaldehyde and corresponding substituted aromatic and heteroaromatic amines by modification of reaction conditions from low to high temperature and from neutral to acidic environment.The antiproliferative activity of chosen substituted isoindolines was assessed on a panel of tumour cell lines and normal human fibroblasts. The majority of tested compounds was active at the highest tested concentrations phenyl-substituted isoindolines 3a and 3b and pyridyl-substituted isoindoline 3g showed a selective effect at micromolar concentrations on HepG2 cell line in comparison with other tested tumour cell lines and normal human fibroblasts. The strongest yet non-selective effect was observed for the pyridyl-substituted isoindoline 8c. These isoindoline derivatives showed diverse mechanism of action on tumour cell death induction as compounds 3a and Sc probably induced mitotic catastrophe while compound 3b induced apoptosis. Indeed. DNA binding properties evidenced that compounds 8a, 8c and 8d bind to DNA as highly potent DNA intercalators. By contrast, compounds 3b, 3e, 3i, 4a and 5 did not target the DNA. At last, the phenyl-substituted compound 8b proved to be a strong DNA binding compound with sequence selective binding and without DNA intercalation profile. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.079

文献信息

• HETEROCYCLIC SUBSTITUTED TRIFLUOROMETHYL PYRIMIDINONES AND THEIR USE
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20160237059A1

  公开（公告）日：2016-08-18

  The present application relates to novel heterocyclically substituted 6-(trifluoromethyl)pyrimidin-4(3H)-one derivatives, to processes for their preparation, to their use alone or in combinations for the treatment and/or prevention of diseases, and to their use for preparing medicaments for the treatment and/or prevention of diseases, in particular for treatment and/or prevention of cardiovascular, renal, inflammatory and fibrotic diseases.

  本申请涉及新颖的杂环取代的6-(三氟甲基)嘧啶-4(3H)-酮衍生物，其制备方法，它们单独或组合用于治疗和/或预防疾病，以及它们用于制备用于治疗和/或预防疾病的药物，特别是用于治疗和/或预防心血管、肾脏、炎症和纤维化疾病。
• TW2016/5831
  申请人：——

  公开号：——

  公开（公告）日：——
• Development of novel inhibitors targeting HIF-1α towards anticancer drug discovery
  作者：Nilambari Yewalkar、Vijaykumar Deore、Amol Padgaonkar、Sonal Manohar、Bichismita Sahu、Pramod Kumar、Archana Jalota-Badhwar、Kalpana S. Joshi、Somesh Sharma、Sanjay Kumar

  DOI：10.1016/j.bmcl.2010.09.083

  日期：2010.11

  Hypoxia-inducible factor-1 alpha (HIF-1 alpha) is a critical regulatory protein of cellular response to hypoxia, and regulates the transcription of many genes involved in key aspects of cancer biology, including immortalization, maintenance of stem cell pools, cellular dedifferentiation, vascularization, and invasion/metastasis. HIF-1 alpha has been implicated in the regulation of genes involved in angiogenesis, for example, VEGF and is associated with tumor progression. In the last decade, over expression of HIF-1 alpha has been demonstrated in many common human cancers and emerging as a validated target for anticancer drug discovery. Here we report the discovery of newly designed and synthesized pyridylpyrimidine based potent and selective inhibitors of HIF-1 alpha. P2630 has been found as potent antiproliferative, antiangiogenic and orally efficacious compound in PC-3 xenograft mice model. (C) 2010 Elsevier Ltd. All rights reserved.
• HETEROCYCLISCH SUBSTITUIERTE TRIFLUORMETHYLPYRIMIDINONE UND IHRE VERWENDUNG
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP3046911A1

  公开（公告）日：2016-07-27
• [DE] HETEROCYCLISCH SUBSTITUIERTE TRIFLUORMETHYLPYRIMIDINONE UND IHRE VERWENDUNG<br/>[EN] HETEROCYCLIC SUBSTITUTED TRIFLUOROMETHYL PYRIMIDINONES AND USE THEREOF<br/>[FR] TRIFLUOROMÉTHYLPYRIMIDONES SUBSTITUÉS PAR UN RADICAL HÉTÉROCYCLIQUE ET LEURS UTILISATION
  申请人：BAYER PHARMA AG

  公开号：WO2015036560A1

  公开（公告）日：2015-03-19

  Die vorliegende Anmeldung betrifft neue, heterocyclisch substituierte 6-(Trifluormethyl)pyrimidin- 4(3H)-on-Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung allein oder in Kombinationen zur Behandlung und/oder Prävention von Krankheiten sowie ihre Verwendung zur Herstellung von Arzneimitteln zur Behandlung und/oder Prävention von Krankheiten, insbesondere zur Behandlung und/oder Prävention von kardiovaskulären, renalen, entzündlichen und fibrotischen Erkrankungen.