2-chloro-N-(3-chlorophenyl)nicotinamide | 57841-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-N-(3-chlorophenyl)nicotinamide
• 英文别名: 2-chloro-N-(3-chloro-phenyl)-nicotinamide；2-chloro-N-(3-chlorophenyl)pyridine-3-carboxamide
• CAS: 57841-56-2
• 化学式: C₁₂H₈Cl₂N₂O
• mdl: MFCD01346314
• 分子量: 267.114
• InChiKey: YFGNIWLKSIIHMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  335.1±37.0 °C(Predicted)
• 密度：
  1.440±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(3-chlorophenyl)nicotinamide 在 盐酸 、 potassium carbonate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 水 为溶剂， 反应 28.0h， 生成 N-(3-chlorophenyl)-2-(4-piperidylamino)nicotinamide
  参考文献：
  名称：

  Synthesis and evaluation of nicotinamide derivative as anti-angiogenic agents

  摘要：

  Previously, we have found that BRN-103, a nicotinamide derivative, inhibits vascular endothelial growth factor (VEGF)-mediated angiogenesis signaling in human endothelial cells. During our continuous efforts to identify more potent anti-angiogenic agents, we synthesized various nicotinamide derivatives and evaluated their anti-angiogenic effects. We found that 2-{1[1-(6-chloro-5-fluoropyrimidin-4-yl)ethyl]piperidin-4-ylamino}-N-(3-chlorophenyl) pyridine-3-carboxamide (BRN-250) significantly inhibited human umbilical vascular endothelial cells (HUVECs) proliferation, migration, tube formation, and microvessel growth in a concentration range of 10-100 nM. Furthermore, BRN-250 inhibited the VEGF-induced phosphorylation and intracellular tyrosine kinase activity of VEGF receptor 2 (VEGFR2) and the activation of its downstream AKT pathway. Taken together, these findings suggest that BRN-250 be considered a potential lead compound for cancer therapy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.125
• 作为产物：
  描述：

  2-氯烟酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.8h， 生成 2-chloro-N-(3-chlorophenyl)nicotinamide
  参考文献：
  名称：

  EP2754655

  摘要：

  公开号：

文献信息

• Compound having angiogenesis inhibitory activity, method for preparing same, and pharmaceutical composition comprising same
  申请人：Kim Ji Han

  公开号：US09227955B2

  公开（公告）日：2016-01-05

  Disclosed are an anti-angiogenic compound, represented by Chemical Formula I, or a pharmaceutically acceptable salt thereof, a preparation method thereof, and a pharmaceutically acceptable composition including the same. Because the compound of Chemical Formula I potently suppresses the angiogenesis, the compound of Chemical Formula I is applicable to the prevention and treatment of diseases caused by aberrant activity of vascular endothelial growth factor, and available as an anti-angiogenic agent.

  本发明公开了一种抗血管生成化合物，其化学式为I，或其药学上可接受的盐，以及其制备方法和包括其的药学上可接受的组合物。由于化合物I的强效抑制血管生成作用，化合物I可用于预防和治疗由血管内皮生长因子异常活动引起的疾病，并可作为抗血管生成剂。
• Synthesis, computational analyses, antibacterial and antibiofilm properties of nicotinamide derivatives
  作者：Ayşe Hümeyra Taşkın Kafa、Gamze Tüzün、Elif Güney、Rukiye Aslan、Koray Sayın、Burak Tüzün、Hilmi Ataseven

  DOI：10.1007/s11224-022-01927-x

  日期：2022.8

  Newly designed nicotinamide derivatives were synthesized and characterized using spectral techniques (IR, 1H-NMR, 13C-NMR, and MS). Moreover, these compounds are investigated computationally. B3LYP/6–31 + G(d,p) level is selected as the calculation level in this study. Experimental and calculated IR spectrum were compared to each other. Electronic properties of synthesized compounds are examined using

  使用光谱技术（IR、 1 H-NMR、13 C-NMR 和 MS）合成和表征了新设计的烟酰胺衍生物。此外，对这些化合物进行了计算研究。本研究选择B3LYP/6-31 + G(d,p)水平作为计算水平。将实验和计算的 IR 光谱相互比较。使用 HOMO/LUMO 等值线图和 MEP 图检查合成化合物的电子特性。通过实验研究了抗菌活性和抗生物膜特性。此外，通过分子对接分析研究了所研究化合物的抗菌特性。结果，发现 ND4 是针对粪肠球菌的最佳抑制剂候选物。
• US2014/256711
  申请人：——

  公开号：——

  公开（公告）日：——
• BRN-103, a novel nicotinamide derivative, inhibits VEGF-induced angiogenesis and proliferation in human umbilical vein endothelial cells
  作者：Hye-Eun Choi、Min-Sang Yoo、Jung-Hye Choi、Jae Yeol Lee、Je Hak Kim、Ji Han Kim、Joon Kwang Lee、Gyu Il Kim、Yong Park、Yong Ha Chi、Soo Heui Paik、Joo Han Lee、Kyung-Tae Lee

  DOI：10.1016/j.bmcl.2011.09.022

  日期：2011.11

  Anti-angiogenesis is regarded as an effective strategy for cancer treatment, and vascular endothelial growth factor (VEGF) plays a key role in the regulations of angiogenesis and vasculogenesis. In the present study, the authors synthesized five novel nicotinamide derivatives which structurally mimic the receptor tyrosine kinase inhibitor sunitinib and evaluated their anti-angiogenic effects. Transwell migration assays revealed that 2-(1-benzylpiperidin-4-yl) amino-N-(3-chlorophenyl) nicotinamide (BRN-103), among the five derivatives most potently inhibited VEGF-induced human umbilical vein endothelial cells (HUVECs). In addition, BRN-103 dose-dependently inhibited VEGF-induced migration, proliferation, and capillary-like tube formation of HUVECs and vessel sprouting from mouse aortic rings. To understand the molecular mechanisms responsible for these activities, the authors examined the effect of BRN-103 on VEGF signaling pathways in HUVECs. BRN-103 was found to suppress the VEGF-induced phosphorylation of VEGF receptor 2 (VEGR2) and the activations of AKT and eNOS. Taken together, these results suggest that BRN-103 inhibits VEGF-mediated angiogenesis signaling in human endothelial cells. (C) 2011 Elsevier Ltd. All rights reserved.
• US20140256711A1
  申请人：——

  公开号：——

  公开（公告）日：——