5-chloro-2-methoxy-N-(3-nitrophenyl)benzamide | 349428-93-9

• 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: 5-chloro-2-methoxy-N-(3-nitrophenyl)benzamide
• CAS: 349428-93-9
• 化学式: C₁₄H₁₁ClN₂O₄
• 分子量: 306.705
• InChiKey: BEQBFECHHLVDMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-2-methoxy-N-(3-nitrophenyl)benzamide 在 tetraphosphorus decasulfide 作用下， 以 吡啶 为溶剂， 以5.3%的产率得到5-chloro-2-methoxy-N-(3-nitrophenyl)benzenecarbothioamide
  参考文献：
  名称：

  Synthesis and in vitro antimycobacterial activity of 2-methoxybenzanilides and their thioxo analogues

  摘要：

  A new series of N-(3/4-substituted phenyl) 4/5-chloro-2-methoxybenzamides and their thioxo analogues have been synthesised and evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv, as well as the two atypical strains Mycobacterium kansasii and Mycobacterium avium. Five of the most active compounds were evaluated for cytotoxicity and their ability to inhibit mycobacterial isocitrate lyase, which is responsible for latent survival of Mycobacterium. The results showed that benzthioanilides were more active than the corresponding benzanilides. The most active compound, 4-chloro-2-methoxy-N-(3,4-dichlorophenyl)benzothioamide (4e), had a minimal inhibition concentration (MIC) against M. tuberculosis of 2 mu mol L-1, which was better than the activity of the previously published corresponding salicylanilide. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.044
• 作为产物：
  描述：

  5-氯-2-甲氧基苯甲酸 、 间硝基苯胺 在 三氯化磷 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以47.5%的产率得到5-chloro-2-methoxy-N-(3-nitrophenyl)benzamide
  参考文献：
  名称：

  Synthesis and in vitro antimycobacterial activity of 2-methoxybenzanilides and their thioxo analogues

  摘要：

  A new series of N-(3/4-substituted phenyl) 4/5-chloro-2-methoxybenzamides and their thioxo analogues have been synthesised and evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv, as well as the two atypical strains Mycobacterium kansasii and Mycobacterium avium. Five of the most active compounds were evaluated for cytotoxicity and their ability to inhibit mycobacterial isocitrate lyase, which is responsible for latent survival of Mycobacterium. The results showed that benzthioanilides were more active than the corresponding benzanilides. The most active compound, 4-chloro-2-methoxy-N-(3,4-dichlorophenyl)benzothioamide (4e), had a minimal inhibition concentration (MIC) against M. tuberculosis of 2 mu mol L-1, which was better than the activity of the previously published corresponding salicylanilide. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.044

文献信息

• [EN] DI(HETERO)ARYLAMIDES AND SULFONAMIDES, METHODS FOR THEIR PREPARATION AND THERAPEUTIC USES THEREOF<br/>[FR] DI(HÉTÉRO)ARYLAMIDES ET SULFONAMIDES, PROCÉDÉS PERMETTANT LEUR PRÉPARATION ET UTILISATIONS THÉRAPEUTIQUES DE CEUX-CI
  申请人：MINORYX THERAPEUTICS S L

  公开号：WO2015014900A1

  公开（公告）日：2015-02-05

  The present invention refers to compounds of formula (I): as well as to a method for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or prevention of conditions associated with the alteration of the activity of β-galactosidase, specially galactosidase beta-1 or GLB1, including GM1 gangliosidoses and Morquio syndrome, type B.

  本发明涉及公式（I）的化合物，以及它们的制备方法，包含这些化合物的药物组合物，以及用于治疗和/或预防与β-半乳糖苷酶活性改变相关的疾病的用途，特别是β-半乳糖苷酶或GLB1的变异，包括GM1神经节苷脂病和莫奎奥综合征B型。
• DI(HETERO)ARYLAMIDES AND SULFONAMIDES, METHODS FOR THEIR PREPARATION AND THERAPEUTIC USES THEREOF
  申请人：MINORYX THERAPEUTICS S.L.

  公开号：US20160168132A1

  公开（公告）日：2016-06-16

  The present invention refers to compounds of formula (I): as well as to a method for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or prevention of conditions associated with the alteration of the activity of β-galactosidase, specially galactosidase beta-1 or GLB1, including GM1 gangliosidoses and Morquio syndrome, type B.

  本发明涉及公式（I）的化合物，以及它们的制备方法、包含它们的药物组合物，以及将其用于治疗和/或预防与β-半乳糖苷酶活性改变相关的疾病的用途，特别是β-半乳糖苷酶或GLB1，包括GM1神经节病和莫尔基奥综合症B型。
• Synthesis and in vitro antimycobacterial activity of 2-methoxybenzanilides and their thioxo analogues
  作者：Ján Kozic、Eva Novotná、Marie Volková、Jiřina Stolaříková、František Trejtnar、Jarmila Vinšová

  DOI：10.1016/j.ejmech.2012.07.044

  日期：2012.10

  A new series of N-(3/4-substituted phenyl) 4/5-chloro-2-methoxybenzamides and their thioxo analogues have been synthesised and evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv, as well as the two atypical strains Mycobacterium kansasii and Mycobacterium avium. Five of the most active compounds were evaluated for cytotoxicity and their ability to inhibit mycobacterial isocitrate lyase, which is responsible for latent survival of Mycobacterium. The results showed that benzthioanilides were more active than the corresponding benzanilides. The most active compound, 4-chloro-2-methoxy-N-(3,4-dichlorophenyl)benzothioamide (4e), had a minimal inhibition concentration (MIC) against M. tuberculosis of 2 mu mol L-1, which was better than the activity of the previously published corresponding salicylanilide. (C) 2012 Elsevier Masson SAS. All rights reserved.