4-氨基-5-硝基烟酰胺 | 911461-18-2

• 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
• 中文名称: 4-氨基-5-硝基烟酰胺
• 英文名称: 4-amino-5-nitronicotinamide
• 英文别名: 4-Amino-5-nitronicotinamide；4-amino-5-nitropyridine-3-carboxamide
• CAS: 911461-18-2
• 化学式: C₆H₆N₄O₃
• 分子量: 182.139
• InChiKey: UJUVARCXCNBQCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 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：
  128
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-氨基-5-硝基烟酰胺 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 24.0h， 生成 2-(piperidin-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-羟基烟酸 在 氯化亚砜 、 硫酸 、 硝酸 、 Ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 4-氨基-5-硝基烟酰胺
  参考文献：
  名称：

  新型咪唑并[4,5- c ]吡啶甲酰胺衍生物作为PARP-1抑制剂的设计，合成及生物学评价

  摘要：

  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。

  DOI：

  10.1016/j.bmcl.2013.02.032

文献信息

• Transformations of ortho-methoxyaryl(hetaryl)carboxamides into quinazolin-4-one and pyrido[2,3-d]pyrimidin-4-one derivatives
  作者：O. B. Ryabova、V. A. Makarov、L. M. Alekseeva、A. S. Shashkov、V. V. Chernyshev、V. G. Granik

  DOI：10.1007/s11172-006-0057-x

  日期：2005.8

  undergo condensation accompanied by the pyrimidine ring closure on refluxing in an excess of sodium methoxide to form bicyclic products, viz., quinazolin-4-one, pyrido[2,3-d]pyrimidin-4-one, and pyrido[4,3-d]pyrimidin-4-one derivatives. The scheme of cyclization processes was proposed. The structures of the reaction products were confirmed by a number of physicochemical data, including X-ray diffraction

  摘要在环的 3 位和/或 5 位含有一个或两个硝基的邻氯芳基（杂芳基）甲酰胺在过量甲醇钠回流时缩合伴随嘧啶环闭合形成双环产物，即喹唑啉-4 -one、pyrido[2,3-d]pyrimidin-4-one 和pyrido[4,3-d]pyrimidin-4-one 衍生物。提出了环化工艺方案。反应产物的结构由许多物理化学数据证实，包括 X 射线衍射分析。
• 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
  作者：Qihua Zhu、Xueyan Wang、Yan Hu、Xiaorong He、Guoqing Gong、Yungen Xu

  DOI：10.1016/j.bmc.2015.09.026

  日期：2015.10

  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.
• 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。