N-(2-氯-4-硝基苯基)苯甲酰胺 | 64160-38-9

• 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: N-(2-氯-4-硝基苯基)苯甲酰胺
• 英文名称: N-(2-chloro-4-nitrophenyl)benzamide
• CAS: 64160-38-9
• 化学式: C₁₃H₉ClN₂O₃
• mdl: MFCD00569246
• 分子量: 276.679
• InChiKey: BCTFYSXVHAFEGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-氯-4-硝基苯基)苯甲酰胺 在 palladium on activated charcoal 、 氢气 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 N-(4-benzamido-3-chlorophenyl)-3-methylfuran-2-carboxamide
  参考文献：
  名称：

  Lead optimization of the VU0486321 series of mGlu1 PAMs. Part 3. Engineering plasma stability by discovery and optimization of isoindolinone analogs

  摘要：

  This Letter describes the further lead optimization of the VU0486321 series of mGlu(1) positive allosteric modulators (PAMs), focused on addressing the recurrent issue of plasma instability of the phthalimide moiety. Here, we evaluated a number of phthalimide bioisosteres, and ultimately identified isoindolinones as the ideal replacement that effectively address plasma instability, while maintaining acceptable mGlu(1) PAM potency, DMPK profile, CNS penetration and mGluR selectivity. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.03.031
• 作为产物：
  描述：

  苯甲酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(2-氯-4-硝基苯基)苯甲酰胺
  参考文献：
  名称：

  针对 SARS-CoV-2 的氯硝柳胺类似物的设计、合成和生物学评价

  摘要：

  氯硝柳胺是一种广泛使用的驱虫药，通过TMEM16F抑制和自噬诱导复制来抑制SARS-CoV-2病毒进入，但相对较高的细胞毒性和较差的口服生物利用度限制了其应用。我们合成了 22 种氯硝柳胺类似物，其中发现化合物5具有最佳的抗 SARS-CoV-2 功效（IC 50  = 0.057 μM)和化合物6、10和11（IC 50 = 0.39、0.38 和 0.49 μM，分别）显示出与氯硝柳胺相当的功效。另一方面，化合物5、6、11在人血浆和肝脏S9酶测定中比氯硝柳胺具有更高的稳定性，口服给药时可以提高生物利用度和半衰期。荧光显微镜显示，与氯硝柳胺相比，化合物5在减少磷脂酰丝氨酸外化方面表现出更好的活性，这与 TMEM16F 抑制有关。应用人工智能预测的人TMEM16F蛋白结构进行分子对接，揭示5的4′-NO 2与Arg809形成氢键，而氯硝柳胺则被2′-Cl阻断。

  DOI：

  10.1016/j.ejmech.2022.114295

文献信息

• Brine-Mediated Efficient Benzoylation of Primary Amines and Amino Acids
  作者：Gautam Chattopadhyay、Suchandra Chakraborty、Chandan Saha

  DOI：10.1080/00397910802250929

  日期：2008.11.3

  Abstract Benzoylation of primary amines and amino acids is efficiently carried out in a brine solution using a stoichiometric amount of benzoyl chloride followed by trituration with aqueous saturated bicarbonate solution.

  摘要 伯胺和氨基酸的苯甲酰化在盐水溶液中使用化学计量的苯甲酰氯有效地进行，然后用饱和碳酸氢盐水溶液研磨。
• A catalytic and tert-butoxide ion-mediated amidation of aldehydes with para-nitro azides
  作者：Giorgio Carbone、James Burnley、John E. Moses

  DOI：10.1039/c3cc40452h

  日期：——

  We report here a new catalytic reaction in which, para-nitro azides are acylated by aldehydes to produce amides and molecular nitrogen in a single step. The transformation is believed to proceed via an electron transfer process mediated by the tert-butoxide ion, and catalysed by a thiazolium salt derived species.

  我们在此报告一种新的催化反应，其中对硝基叠氮化合物通过醛的酰基化作用，一步生成酰胺和分子氮。该转化过程被认为是由叔丁醇盐离子介导的电子转移过程，并经由噻唩盐衍生物催化完成。
• Mild, Efficient and Selective Nitration of Anilides, Non-Activated and Moderately Activated Aromatic Compounds with Ammonium Molybdate and Nitric Acid as a New Nitrating Agent
  作者：Sariah Sana、K. C. Rajanna、Mir Moazzam Ali、P. K. Saiprakash

  DOI：10.1246/cl.2000.48

  日期：2000.1

  inexpensive reagent. Regioselective nitration of anilides, non-activated and moderately activated aromatic compounds could be afforded by employing ammonium molybdate and nitric acid as mild and effective nitrating agent. This procedure works efficiently under reflux conditions to prepare mononitroderivatives of anilides, non-activated and moderately activated aromatic compounds in good to excellent yield with

  钼酸铵 [Mo(VI)] 是一种操作简单、环境安全且价格低廉的试剂。使用钼酸铵和硝酸作为温和有效的硝化剂，可以对苯胺、未活化和中等活化的芳香族化合物进行区域选择性硝化。该程序在回流条件下有效地制备了苯胺、未活化和中等活化的芳族化合物的单硝基衍生物，收率良好，具有高区域选择性。
• ZnCl2/PhI=O Mediated Selective ortho-Chlorination of Amides
  作者：Haixuan Liu、Qiang Sha

  DOI：10.2174/1570178618666210624115748

  日期：2022.3

  A new ortho-chlorination system consisting of zinc(II) and hypervalent iodine(III) reagent was developed for ortho-chlorination of amides, and the desired products were obtained in moderate to good yields (38-85%). This highly facile and convenient methodology is tolerant of aromatic amide and alkyl amide with diverse substituted groups. A plausible mechanism has been illustrated, in which carbocation rearrangement and metal salt coordinate facilitated orthochlorination are involved.

  摘要：开发了一种新的由锌(II)和高价碘(III)试剂组成的正氯化体系，用于酰胺的正氯化反应，并以中等至良好的收率（38-85%）获得所需产物。这种高度简便和方便的方法对具有不同取代基的芳香酰胺和烷基酰胺具有耐受性。已经阐明了一个合理的机理，其中包括离子重排和金属盐协助的正氯化反应。
• Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
  申请人：American Home Products Corporation

  公开号：US20010039348A1

  公开（公告）日：2001-11-08

  Compounds having the formula: 1 wherein R 1 -R 5 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 carbon members, aryl, heteroaryl, halogen, —CN, —NO 2 , —CO 2 R 6 , —COR 6 , —OR 6 , —SR 6 , —SOR 6 , —SO 2 R 6 , —CONR 7 R 8 , —NR 6 N(R 7 R 8 ), —N(R 7 R 8 ) or W-Y-(CH 2 ) n -Z provided that at least one of R 1 -R 5 is not hydrogen; or R 1 and R 2 or R 3 and R 4 , taken together form a 3 to 7 membered heterocycloalkyl or 3 to 7 membered heteroaryl; R 6 and R 7 are independently hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, or aryl; R 8 is hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 members, aryl or heteroaryl, or R 7 and R 8 , taken together may form a 3 to 7 membered heterocycloalkyl; W is O, NR 6 , or is absent; Y is —(CO)— or —(CO 2 )—, or is absent; Z is alkyl of 1 to 4 carbon atoms, —CN, —CO 2 R 6 , COR 6 , —CONR 7 R 8 , —OCOR 6 , —NR 6 COR 7 , —OCONR 6 , —OR 6 , —SR 6 , —SOR 6 , —SO 2 R 6 , SR6N(R7R8), —N(R 7 R 8 ) or phenyl; G is aryl or fused bicyclic heteroaryl; X is a bond, —NH, alkyl of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, alkylamino of 1 to 6 carbon atoms, or (CH)J; J is alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, phenyl or benzyl; and n is an integer from 1 to 6; useful in the treatment of diseases associated with herpes viruses including human cytomegalovirus, herpes simplex viruses, Epstein-Barr virus, varicella-zoster virus, human herpesviruses-6 and -7, and Kaposi herpesvirus.

  化合物的化学式为1，其中R1-R5独立选择自氢、1到6个碳原子的烷基、2到6个碳原子的烯基、2到6个碳原子的炔基、1到6个碳原子的全卤烷基、3到10个碳原子的环烷基、3到10个碳成员的杂环烷基、芳基、杂芳基、卤素、-CN、-NO2、-CO2R6、-COR6、-OR6、-SR6、-SOR6、-SO2R6、-CONR7R8、-NR6N（R7R8）、-N（R7R8）或W-Y-（CH2）n-Z，其中至少一个R1-R5不是氢；或R1和R2或R3和R4，一起形成3到7个成员的杂环烷基或3到7个成员的杂芳基；R6和R7独立地为氢、1到6个碳原子的烷基、1到6个碳原子的全卤烷基或芳基；R8为氢、1到6个碳原子的烷基、1到6个碳原子的全卤烷基、3到10个碳原子的环烷基、3到10个成员的杂环烷基、芳基或杂芳基，或R7和R8一起形成3到7个成员的杂环烷基；W为O、NR6或不存在；Y为-CO-或-CO2-，或不存在；Z为1到4个碳原子的烷基、-CN、-CO2R6、COR6、-CONR7R8、-OCOR6、-NR6COR7、-OCONR6、-OR6、-SR6、-SOR6、-SO2R6、SR6N（R7R8）、-N（R7R8）或苯基；G为芳基或融合的双环杂芳基；X为键、-NH、1到6个碳原子的烷基、1到6个碳原子的烯基、1到6个碳原子的烷氧基、1到6个碳原子的硫代烷基、1到6个碳原子的烷基氨基或（CH）J；J为1到6个碳原子的烷基、3到7个碳原子的环烷基、苯基或苄基；n为1到6的整数。该化合物可用于治疗与疱疹病毒相关的疾病，包括人类巨细胞病毒、单纯疱疹病毒、EB病毒、水痘-带状疱疹病毒、人类疱疹病毒-6和-7以及卡波西疱疹病毒。

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