4-chloro-trans-cinnamic acid-(2-chloro-anilide) | 110179-64-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-chloro-trans-cinnamic acid-(2-chloro-anilide)
• 英文别名: 4-Chlor-trans-zimtsaeure-(2-chlor-anilid)；(E)-N-(2-chlorophenyl)-3-(4-chlorophenyl)prop-2-enamide
• CAS: 110179-64-1
• 化学式: C₁₅H₁₁Cl₂NO
• 分子量: 292.164
• InChiKey: OIWLZTDNOLCJAV-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  丙酸,3-[(2-氯苯基)氨基]-3-羰基- 、 4-氯苯甲醛 生成 4-chloro-trans-cinnamic acid-(2-chloro-anilide)
  参考文献：
  名称：

  School Nurses Identify Barriers and Solutions to Implementing a School-Based Hepatitis B Immunization Program

  摘要：

  DOI：

  10.1111/j.1746-1561.2002.tb06531.x

文献信息

• Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides
  作者：Tomas Strharsky、Dominika Pindjakova、Jiri Kos、Lucia Vrablova、Hana Michnova、Jan Hosek、Nicol Strakova、Veronika Lelakova、Lenka Leva、Lenka Kavanova、Michal Oravec、Alois Cizek、Josef Jampilek

  DOI：10.3390/ijms23063159

  日期：——

  A series of eighteen 4-chlorocinnamanilides and eighteen 3,4-dichlorocinnamanilides were designed, prepared and characterized. All compounds were evaluated for their activity against gram-positive bacteria and against two mycobacterial strains. Viability on both cancer and primary mammalian cell lines was also assessed. The lipophilicity of the compounds was experimentally determined and correlated together with other physicochemical properties of the prepared derivatives with biological activity. 3,4-Dichlorocinnamanilides showed a broader spectrum of action and higher antibacterial efficacy than 4-chlorocinnamanilides; however, all compounds were more effective or comparable to clinically used drugs (ampicillin, isoniazid, rifampicin). Of the thirty-six compounds, six derivatives showed submicromolar activity against Staphylococcus aureus and clinical isolates of methicillin-resistant S. aureus (MRSA). (2E)-N-[3,5-bis(trifluoromethyl)phenyl]- 3-(4-chlorophenyl)prop-2-enamide was the most potent in series 1. (2E)-N-[3,5-bis(Trifluoromethyl)phenyl]-3-(3,4-dichlorophenyl)prop-2-enamide, (2E)-3-(3,4-dichlorophenyl)-N-[3-(trifluoromethyl)phenyl]prop-2-enamide, (2E)-3-(3,4-dichloro- phenyl)-N-[4-(trifluoromethyl)phenyl]prop-2-enamide and (2E)-3-(3,4-dichlorophenyl)- N-[4-(trifluoromethoxy)phenyl]prop-2-enamide were the most active in series 2 and in addition to activity against S. aureus and MRSA were highly active against Enterococcus faecalis and vancomycin-resistant E. faecalis isolates and against fast-growing Mycobacterium smegmatis and against slow-growing M. marinum, M. tuberculosis non-hazardous test models. In addition, the last three compounds of the above-mentioned showed insignificant cytotoxicity to primary porcine monocyte-derived macrophages.

  设计、制备并表征了18种4-氯肉桂酰胺和18种3,4-二氯肉桂酰胺。评估了所有化合物对革兰氏阳性菌和两种分枝杆菌菌株的活性。还评估了化合物在癌细胞和原代哺乳动物细胞系上的存活率。实验测定了化合物的亲脂性，并将其与所制备衍生物的其他物理化学性质相关联，以探究其生物活性。3,4-二氯肉桂酰胺表现出更广泛的作用谱和更高的抗菌效力，而所有化合物都比临床使用的药物（氨苄青霉素、异烟肼、利福平）更有效或相当。在36种化合物中，有6种衍生物对金黄色葡萄球菌和甲氧西林耐药金黄色葡萄球菌（MRSA）表现出亚微米级的活性。在第一系列中，(2E)-N-[3,5-双(三氟甲基)苯基]-3-(4-氯苯基)丙-2-烯酰胺是最有效的。在第二系列中，(2E)-N-[3,5-双(三氟甲基)苯基]-3-(3,4-二氯苯基)丙-2-烯酰胺、(2E)-3-(3,4-二氯苯基)-N-[3-(三氟甲基)苯基]丙-2-烯酰胺、(2E)-3-(3,4-二氯苯基)-N-[4-(三氟甲基)苯基]丙-2-烯酰胺和(2E)-3-(3,4-二氯苯基)-N-[4-(三氟甲氧基)苯基]丙-2-烯酰胺是最活跃的，并且除了对S. aureus和MRSA的活性外，还高度活跃于肠球菌和万古霉素耐药肠球菌分离株以及快速生长的结核分枝杆菌和缓慢生长的海水分枝杆菌等非危险性试验模型。此外，上述最后三种化合物对初代猪单核细胞衍生的巨噬细胞具有极小的细胞毒性。
• [EN] PREPARATION METHOD OF QUINOLINE DERIVATIVE COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS DÉRIVÉS DE QUINOLÉINE
  申请人：ABIVAX

  公开号：WO2022200426A1

  公开（公告）日：2022-09-29

  The present invention relates to a method for preparing a compound of formula (I) comprising the following steps: (i) reacting a compound of formula (II) with a compound of formula (III), to form the hydrochloride salt of the compound of formula (I), wherein the molar ratio of the compound of formula (II) vs. the compound of formula (III) is from 1.00:0.80 to 1.00:1.20, and no metal catalyst is present, and (ii) recovering the compound of formula (I) in the form of a free base through addition of a base. The present invention also relates to a powder obtained by said method and a powder comprising a compound of formula (I) which is characterized by a particle size distribution with specific D50, D90 and/or D10 values, and a pharmaceutical composition comprising said powders and at least one pharmaceutically acceptable excipient.

  本发明涉及一种制备式(I)化合物的方法，包括以下步骤：(i)将式(II)化合物与式(III)化合物反应，形成式(I)化合物的盐酸盐，其中式(II)化合物与式(III)化合物的摩尔比为1.00:0.80至1.00:1.20，且无金属催化剂存在；(ii)通过加入碱，以自由碱的形式回收式(I)化合物。本发明还涉及通过该方法获得的粉末以及具有特定D50、D90和/或D10值的式(I)化合物的粉末，以及包含该粉末和至少一种药用辅料的制药组合物。
• School Nurses Identify Barriers and Solutions to Implementing a School-Based Hepatitis B Immunization Program
  作者：Andrea D. Guajardo、Amy B. Middleman、Kim M. Sansaricq

  DOI：10.1111/j.1746-1561.2002.tb06531.x

  日期：2002.3