N-Chloracetyl-N'-<3-methoxy-phenyl>-harnstoff | 16615-80-8

• 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: N-Chloracetyl-N'-<3-methoxy-phenyl>-harnstoff
• 英文别名: N-Chloracetyl-N'-(3-methoxy-phenyl)-harnstoff；2-Chloro-N-[(3-methoxyphenyl)carbamoyl]acetamide
• CAS: 16615-80-8
• 化学式: C₁₀H₁₁ClN₂O₃
• 分子量: 242.662
• InChiKey: WGDSMOZJAPHSMG-UHFFFAOYSA-N

物化性质

• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Chloracetyl-N'-<3-methoxy-phenyl>-harnstoff 、 8-chloro-5H-[1,2,4]triazino[5,6-b]indole-3-thiol 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-[(8-chloro-5H-[1,2,4]triazino[5,6-b]indol-3-yl)sulfanyl]-N-[(3-methoxyphenyl)carbamoyl]acetamide
  参考文献：
  名称：

  Sengupta; Pandey; Verma, Journal of the Indian Chemical Society, 1985, vol. 62, # 2, p. 165 - 168

  摘要：

  DOI：
• 作为产物：
  描述：

  氯乙酰异氰酸酯 、 间氨基苯甲醚 以 二氯甲烷 为溶剂， 生成 N-Chloracetyl-N'-<3-methoxy-phenyl>-harnstoff
  参考文献：
  名称：

  Quinoxaline-based inhibitors of Ebola and Marburg VP40 egress

  摘要：

  We prepared a series of quinoxalin-2-mercapto-acetyl-urea analogs and evaluated them for their ability to inhibit viral egress in our Marburg and Ebola VP40 VLP budding assays in HEK293T cells. We also evaluated selected compounds in our bimolecular complementation assay (BiMC) to detect and visualize a Marburg mVP40-Nedd4 interaction in live mammalian cells. Antiviral activity was assessed for selected compounds using a live recombinant vesicular stomatitis virus (VSV) (M40 virus) that expresses the EBOV VP40 PPxY L-domain. Finally selected compounds were evaluated in several ADME assays to have an early assessment of their drug properties. Our compounds had low nM potency in these assays (e.g., compounds 21, 24, 26, 39), and had good human liver microsome stability, as well as little or no inhibition of P450 3A4. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.06.053

文献信息

• Design, Synthesis, and Antitumor Activity Evaluation of Trifluoromethyl-Substituted Pyrimidine Derivatives Containing Urea Moiety
  作者：Liu Limin、Wang Zhengjie、Liu Xiujuan、Gao Chao、Dai Honglin、Wang Tao、Li Na、Yan Heyi、Zhang Yang、Zhang Luye、Zheng Jiaxin、Shan Lihong、Liu Hongmin、Zhang Qiurong

  DOI：10.1134/s1068162021060157

  日期：2021.11

  Abstract In order to find efficient new antitumor drugs, a series of novel pyrimidine derivatives containing urea moiety were designed and synthesized, and the antitumor activity of four human tumor cells was evaluated by MTT analysis. The results showed that most of the target compounds exhibited moderate antitumor activity. In particular, the IC50 (concentration required to achieve 50% inhibition

  摘要 为了寻找有效的新型抗肿瘤药物，设计合成了一系列含有尿素部分的新型嘧啶衍生物，并通过MTT分析评估了四种人肿瘤细胞的抗肿瘤活性。结果表明，大多数目标化合物表现出中等的抗肿瘤活性。特别地，化合物2-((4-(4-乙基苯氧基)-6-(三氟甲基)嘧啶-2-基)硫代) -N的IC 50 (实现50%抑制肿瘤细胞增殖所需的浓度)值-((4-乙基苯基)carba-moyl)乙酰胺对于 MGC-803（人胃癌细胞系）为 2.51 ± 0.17 µmol L –1，抗增殖活性明显优于阳性对照药物5-氟尿嘧啶。分子对接表明，该化合物可以与表皮生长因子受体（EGFR）的活性位点结合良好，有可能成为潜在的抗肿瘤药物。
• Discovery of 1,3,4-oxadiazole derivatives containing a bisamide moiety as a novel class of potential cardioprotective agents
  作者：Fei-Fei Yang、Jin-Zhu Zhou、Xue-Li Xu、Ting Hu、Jian-Quan Liu、Ya-Xi Wu、Bo Wei、Li-Ying Ma

  DOI：10.1016/j.ejmech.2022.114526

  日期：2022.9

  a lead compound 12a containing 1,3,4-oxadiazole by extensive screening of anticancer derivatives containing nitrogen-heterocycle, which exhibited potential protective activity against oxidative stress in cardiomyocytes. Follow-up structure-activity relationship (SAR) studies also highlighted the role of substitution sites and bisamide moiety in enhancing the protective activity against oxidative stress

  心肌损伤是心血管疾病和癌症治疗中不可忽视的问题。含氮杂环化合物在心血管领域的功能特性近年来备受关注。在此，我们通过广泛筛选含有氮杂环的抗癌衍生物发现了一种含有 1,3,4-恶二唑的先导化合物12a ，该化合物对心肌细胞的氧化应激表现出潜在的保护活性。后续的构效关系 (SAR) 研究还强调了取代位点和双酰胺部分在增强抗氧化应激保护活性中的作用。具体来说，化合物12d在高浓度下表现出低细胞毒性，并在 H9c2 细胞中表现出对氧化应激的有效心肌保护作用。初步机制研究表明，化合物12d可降低心肌肥大和氧化应激相关蛋白/基因的表达，减少线粒体介导的细胞凋亡，从而增强受损心肌细胞的细胞活力。在本研究中，1,3,4-恶二唑可能代表了一种具有潜在心肌保护作用的新型药效团，为未来心血管药物的优化提供了更多选择，特别是用于治疗肿瘤心脏病学。
• Soni; Bhalla; Gupta, European Journal of Medicinal Chemistry, 1985, vol. 20, # 2, p. 190 - 192
  作者：Soni、Bhalla、Gupta、et al.

  DOI：——

  日期：——
• Mehrotra, Suman; Barthwal, J. P.; Saxena, A. K., Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1157 - 1159
  作者：Mehrotra, Suman、Barthwal, J. P.、Saxena, A. K.、Bhargava, K. P.、Parmar, S. S.

  DOI：——

  日期：——
• Gupta, Anil K. Sen; Rastogi, Anita; Hajela, Kanchan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 10, p. 1074 - 1075
  作者：Gupta, Anil K. Sen、Rastogi, Anita、Hajela, Kanchan

  DOI：——

  日期：——