4,5-diaminonicotinamide | 1428261-70-4

• 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: 4,5-diaminonicotinamide
• 英文别名: 4,5-Diaminopyridine-3-carboxamide
• CAS: 1428261-70-4
• 化学式: C₆H₈N₄O
• 分子量: 152.156
• InChiKey: AKJWTSXLOIMLBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  412.5±45.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 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：
  108
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-diaminonicotinamide 在 palladium 10% on activated carbon 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.08h， 生成 2-(1-propylpiperidin-4-yl)-3H-imidazo[4,5-c]pyridine-7-carboxamide
  参考文献：
  名称：

  Discovery and SAR study of 2-(1-propylpiperidin-4-yl)-3H-imidazo[4,5-c]pyridine-7-carboxamide: A potent inhibitor of poly(ADP-ribose) polymerase-1 (PARP-1) for the treatment of cancer

  摘要：

  A series of imidazo[4,5-c]pyridine-7-carboxamide derivatives as poly(ADP-ribose) polymerase (PARP) inhibitors have been developed. All target compounds were evaluated for their PARP-1 inhibitory activity and some were further assessed for cellular potency. These efforts led to identification of a novel PARP-1 inhibitor 2-(1-propylpiperidin-4-yl)-3H-imidazo[4,5-c]pyridine-7-carboxamide 11a (XZ-120312). 11a displayed strong inhibition against the PARP-1 enzyme with an IC50 of 8.6 +/- 0.6 nM and excellent potentiation of temozolomide cytotoxicity in cancer cell lines SW-620, MDA-MB-468 and A549 by 4.0, 3.0 and 7.7 times, respectively. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.026
• 作为产物：
  描述：

  4-氨基-5-硝基烟酰胺 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 4,5-diaminonicotinamide
  参考文献：
  名称：

  Discovery and SAR study of 2-(1-propylpiperidin-4-yl)-3H-imidazo[4,5-c]pyridine-7-carboxamide: A potent inhibitor of poly(ADP-ribose) polymerase-1 (PARP-1) for the treatment of cancer

  摘要：

  A series of imidazo[4,5-c]pyridine-7-carboxamide derivatives as poly(ADP-ribose) polymerase (PARP) inhibitors have been developed. All target compounds were evaluated for their PARP-1 inhibitory activity and some were further assessed for cellular potency. These efforts led to identification of a novel PARP-1 inhibitor 2-(1-propylpiperidin-4-yl)-3H-imidazo[4,5-c]pyridine-7-carboxamide 11a (XZ-120312). 11a displayed strong inhibition against the PARP-1 enzyme with an IC50 of 8.6 +/- 0.6 nM and excellent potentiation of temozolomide cytotoxicity in cancer cell lines SW-620, MDA-MB-468 and A549 by 4.0, 3.0 and 7.7 times, respectively. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.026

文献信息

• [EN] PIPERIDIN-1- YL-N-PYRYDI NE-3-YL-2-OXOACET AM IDE DERIVATIVES USEFUL FOR THE TREATMENT OF MTAP-DEFICIENT AND/OR MT A-ACCUMULATING CANCERS<br/>[FR] DÉRIVÉS DE PIPÉRIDIN-1-YL-N-PYRYDINE-3-YL-2-OXO-ACÉTAMIDE UTILES POUR LE TRAITEMENT DE CANCERS DÉFICIENTS EN MTAP ET/OU ACCUMULANT MTA
  申请人：TANGO THERAPEUTICS INC

  公开号：WO2022026892A1

  公开（公告）日：2022-02-03

  Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R1, R2, R3, R4, R6, R7, R8 and n are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

  根据公式（I）提供化合物及其药用盐，以及药物组合物；其中R1、R2、R3、R4、R6、R7、R8和n的定义如本文所述。本发明的化合物被认为对预防和治疗各种疾病条件有用。
• Design, synthesis and biological evaluation of novel imidazo[4,5-c]pyridinecarboxamide derivatives as PARP-1 inhibitors
  作者：Qihua Zhu、Xuyan Wang、Zhaoxing Chu、Guangwei He、Guangping Dong、Yungen Xu

  DOI：10.1016/j.bmcl.2013.02.032

  日期：2013.4

  A series of novel cyclic amine-substituted imidazo[4,5-c]pyridinecarboxamide analogs were designed and synthesized. All the target compounds were evaluated for their PARP inhibition activity, and the result indicated that most of the compounds possessed inhibitory effect on PARP at the concentration of 1 μM, among which compound 8d (IC50 = 0.528 μM) was selected for evaluating the antitumor effect

  设计并合成了一系列新型的环胺取代的咪唑并[4,5- c ]吡啶甲酰胺类似物。评价所有目标化合物的PARP抑制活性，结果表明大多数化合物在1μM的浓度下对PARP具有抑制作用，其中选择化合物8d（IC 50  = 0.528μM）评估其抗肿瘤活性。体内作用。结果显示化合物8d和顺铂组合组在小鼠A549模型中的抗肿瘤功效与ABT-888和顺铂组合组的相似。
• COMPOUNDS AND METHODS OF USE
  申请人：Tango Therapeutics, Inc.

  公开号：US20220127256A1

  公开（公告）日：2022-04-28

  Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 and n are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.