4-氯甲基-N-苯基苯甲酰胺 | 226250-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯甲基-N-苯基苯甲酰胺
• 英文名称: 4-(chloromethyl)-N-phenylbenzamide
• 英文别名: 4-chloromethyl-N-phenylbenzamide；4-(N-phenylcarbamoyl)benzyl chloride；4-chloromethyl-N-phenyl-benzamide
• CAS: 226250-00-6
• 化学式: C₁₄H₁₂ClNO
• mdl: MFCD08444337
• 分子量: 245.708
• InChiKey: HFNFRLAPRHDADV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-氯甲基-N-苯基苯甲酰胺 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 以49.6%的产率得到4-(hydroxymethyl)-N-phenyl benzamide
  参考文献：
  名称：

  New microtubule polymerization inhibitors comprising a nitrooxymethylphenyl group

  摘要：

  We have designed cancer antiproliferative compounds, starting from aniline or phenol derivative, which comprise one or two nitrooxymethylphenyl groups as do the hybrid drugs NCX4040 and NCX530. Compound 2a with p-nitrooxymethylbenzoyl-oxy and -amino groups as well as 8a with a p-nitrooxymethylbenzoylamino group showed more promising effects than NCX4040 against human colon and breast cancer cells. Since 2a and 8a, but not NCX4040, arrested human colon carcinoma HCT116 cells in the M phase, the former two compounds may inhibit cell growth differently from NCX4040. Merged images of immunofluorescence-stained a-tubulin and Hoechst-stained nuclei in human fibrosarcoma HT1080 cells showed that 2a and 8a disrupted microtubule formation just as did vincristine, the tubulin polymerization inhibitor. In experiments in vivo, the intraperitoneal administration of 8a at 80 mg/kg/day reduced the growth of HCT116 xenografts in nude mice to T/C 55%. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.031
• 作为产物：
  描述：

  对醛基苯甲酸 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.5h， 生成 4-氯甲基-N-苯基苯甲酰胺
  参考文献：
  名称：

  带有 4-(芳基氨基甲酰基)苄基的新型氟喹诺酮类似物：设计、合成和抗菌评估

  摘要：

  全球细菌对氟喹诺酮的耐药性正在以惊人的速度增加。为了寻找更有效的抗菌剂，我们采用了一种高效、简单的方案来获得与 4-(芳基氨基甲酰基)苄基7a-ab缀合的新型环丙沙星和沙拉沙星类似物的大底物范围。所有制备的化合物均针对三种革兰氏阳性菌株（耐甲氧西林金黄色葡萄球菌（MRSA）、金黄色葡萄球菌和粪肠球菌）以及三种革兰氏阴性菌株（铜绿假单胞菌、肺炎克雷伯菌和埃希氏菌）进行了抗菌活性评估。大肠杆菌）通过三种标准方法，包括肉汤微量稀释、琼脂盘扩散和琼脂井扩散测定。大多数化合物对 MRSA 和金黄色葡萄球菌表现出极好的抗菌效力。在目标化合物中，衍生物7n表现出很强的抗菌效力，明显比母体环丙沙星更有效。随后，对该化合物进行了分子对接研究，以找出其与金黄色葡萄球菌DNA 旋转酶（PDB ID：2XCT）活性位点可能的结合模式。

  DOI：

  10.1007/s11030-023-10676-w

文献信息

• ANTI-VIRAL COMPOUNDS, COMPOSITIONS, AND METHODS OF USE
  申请人：Leivers Martin Robert

  公开号：US20090226398A1

  公开（公告）日：2009-09-10

  Disclosed are compounds and compositions of Formula (I), pharmaceutically acceptable salts and solvates thereof, and their preparation and uses for treating viral infections mediated at least in part by a virus in the Flaviviridae family of viruses.

  披露了公式(I)的化合物和组合物、药物可接受的盐和溶剂化物，以及它们的制备和使用，用于治疗至少部分由黄病毒科病毒家族中的病毒介导的病毒感染。
• Cyclic amine derivatives and their use as drugs
  申请人：Teijin Limited

  公开号：US06362177B1

  公开（公告）日：2002-03-26

  A compound represented by the general formula (I), a pharmaceutically acceptable acid addition salt thereof or a pharmaceutically acceptable C1-C6 alkyl addition salt thereof, and their medical applications. These compounds inhibit the action of chemokines such as MIP-1&agr; and/or MCP-1 on target cells, and are useful as therapeutic and/or preventative drugs in diseases, such as atheroclerosis, rheumatoid arthritis, and the like where blood monocytes and lymphocytes infiltrate into tissues.

  一种由通式（I）表示的化合物，其药学上可接受的酸盐或药学上可接受的C1-C6烷基盐，以及它们的医药应用。这些化合物抑制趋化因子如MIP-1α和/或MCP-1对靶细胞的作用，并可用作治疗和/或预防药物，用于动脉粥样硬化、类风湿性关节炎等疾病，其中血液单核细胞和淋巴细胞浸润到组织中。
• [EN] THIOPHENE HETEROARYL AMINES<br/>[FR] HETEROARYLAMINES DE TIOPHENE
  申请人：SUGEN INC

  公开号：WO2005113548A1

  公开（公告）日：2005-12-01

  The present invention relates to thiophene heteroaryl amines and their pharmaceutically acceptable salts that modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer. Formula (I).

  本发明涉及噻吩杂环芳基胺及其药用可接受盐，能调节蛋白激酶的活性，因此预计在预防和治疗蛋白激酶相关的细胞疾病，如癌症方面具有用处。化学式（I）。
• Synthesis and Biological Evaluation of 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives as Potential Cytotoxic Agents
  作者：Yao-Jie Shi、Xue-Jiao Song、Xiao Li、Ting-Hong Ye、Ying Xiong、Luo-Ting Yu

  DOI：10.1248/cpb.c13-00242

  日期：——

  A series of new 3-amino-5-sulfanyl-1,2,4-triazole and 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives have been synthesized and their cytotoxicities were evaluated on a panel of human cancer cell lines (BxPC-3, H1975, SKOV-3, A875, HCT116, etc.). The best one (compound 5m) exhibited activities with IC50 values ranging from 0.04 to 23.6 µM against nine human cancer cell lines. Further biological evaluation indicated that DNA replication was blocked by treatment with compound 5m in HCT116 cells.

  一系列新的3-氨基-5-硫氨基-1,2,4-噻唑和2-氨基-5-硫氨基-1,3,4-噻二唑衍生物已经合成，并对一系列人癌细胞系（BxPC-3、H1975、SKOV-3、A875、HCT116等）进行了细胞毒性评估。最佳化合物（5m）的活性在九种人癌细胞系中展现出IC50值范围为0.04至23.6 µM。进一步的生物学评估显示，HCT116细胞中用化合物5m处理后，DNA复制被阻断。
• Synthesis and &lt;i&gt;in Vitro&lt;/i&gt; Antiproliferative Evaluation of Novel Hybrids from 1,3,4-Thiadiazole and Benzisoselenazolone
  作者：Fen Jing、Xiaoyun Fu、Sha Li、Baolin Li、Jijun Zhao、Xuefeng Wang、Yuming Liu、Baoquan Chen

  DOI：10.1248/cpb.c15-00014

  日期：——

  Novel hybrids from 1,3,4-thiadiazole and benzisoselenazolone were designed, synthesized and evaluated for their in vitro antiproliferative activities by CCK-8 assay against three types of human cancer cell lines, SMMC-7721, MCF-7 and A549 cells. The preliminary bioassay results demonstrated that all tested compounds 4a–p showed potent antiproliferative activities, and some compounds exhibited better effects than positive control ethaselen and 5-fluorouracil (5-FU) against various cancer cell lines. Furthermore, compound 4g showed significant antiproliferative activities against SMMC-7721 cells with an IC50 value of 2.08 µM. Compounds 4b and 4m displayed highly effective biological activities against MCF-7 cells with an IC50 values of 2.03 and 2.06 µM, respectively. Compound 4i exhibited the best inhibitory effect against A549 cells with an IC50 value of 1.03 µM.

  设计、合成并评估了由1,3,4-噻二唑和苯异硒氮唑组成的新型杂化物的体外抗增殖活性，通过CCK-8法对三种人癌细胞系SMMC-7721、MCF-7和A549进行测试。初步生物测定结果表明，所有检测的化合物4a–p均表现出强效的抗增殖活性，并且某些化合物在不同癌细胞系中表现出优于阳性对照药物乙硒醇和5-氟尿嘧啶（5-FU）的效果。此外，化合物4g对SMMC-7721细胞表现出显著的抗增殖活性，IC50值为2.08 µM。化合物4b和4m对MCF-7细胞表现出非常有效的生物活性，IC50值分别为2.03和2.06 µM。化合物4i对A549细胞的抑制效果最佳，IC50值为1.03 µM。