N-hydroxy-4-{[2-(3-methoxyphenyl)acetamido]methyl}benzamide

• 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-hydroxy-4-{[2-(3-methoxyphenyl)acetamido]methyl}benzamide
• 英文别名: N-hydroxy-4-[[[2-(3-methoxyphenyl)acetyl]amino]methyl]benzamide
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: QVSVBEZHVVAIBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲氧基苯基乙酰氯 在 N-甲基吗啉 、 氯甲酸乙酯 、 三乙胺 、 lithium hydroxide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 N-hydroxy-4-{[2-(3-methoxyphenyl)acetamido]methyl}benzamide
  参考文献：
  名称：

  Synthesis of aminophenylhydroxamate and aminobenzylhydroxamate derivatives and in vitro screening for antiparasitic and histone deacetylase inhibitory activity

  摘要：

  A series of aminophenylhydroxamates and aminobenzylhydroxamates were synthesized and screened for their antiparasitic activity against Leishmania, Trypanosoma, and Toxoplasma. Their anti-histone deacetylase (HDAC) potency was determined. Moderate to no antileishmanial or antitrypanosomal activity was found (IC50 > 10 mu M) that contrast with the highly efficient anti-Toxoplasma activity (IC50 < 1.0 mu M) of these compounds. The antiparasitic activity of the synthetized compounds correlates well with their HDAC inhibitory activity. The best-performing compound (named 363) express a high anti-HDAC6 inhibitory activity (IC50 of 0.045 +/- 0.015 mu M) a moderate cytotoxicity and a high anti-Toxoplasma activity in the range of known anti-Toxoplasma compounds (IC50 of 0.35-2.25 mu M). The calculated selectivity index (10-300 using different human cell lines) of the compound 363 makes it a lead compound for the future development of anti-Toxoplasma molecules.

  DOI：

  10.1016/j.ijpddr.2018.01.002

文献信息

• [EN] NEW COMPOUNDS FOR THE TREATMENT AND/OR PREVENTION OF PARASITIC DISEASES AND METHOD OF PRODUCTION OF THEREOF<br/>[FR] NOUVEAUX COMPOSÉS POUR LE TRAITEMENT ET/OU LA PRÉVENTION DE MALADIES PARASITAIRES ET LEUR PROCÉDÉ DE PRODUCTION
  申请人：INST RECH DEVELOPPEMENT IRD

  公开号：WO2015007870A1

  公开（公告）日：2015-01-22

  The present invention relates to new compounds for treating, preventing or inhibiting a parasitic disease, preferably toxoplasmosis in a subject, the method for preparing thereof.

  本发明涉及用于治疗、预防或抑制寄生虫病的新化合物，优选用于治疗弓形虫病。同时，本发明还涉及该化合物的制备方法。
• Compounds for the treatment and/or prevention of parasitic diseases and method of production thereof
  申请人：Institut de Recherche pour le Développement ( IRD)

  公开号：EP2826769A1

  公开（公告）日：2015-01-21

  The present invention relates to new compounds for treating, preventing or inhibiting a parasitic disease, preferably toxoplasmosis in a subject, the method for preparing thereof.

  本发明涉及治疗、预防或抑制寄生虫病的新化合物，优选用于治疗猫传播性弓形虫病，以及其制备方法。
• COMPOUNDS FOR THE TREATMENT AND/OR PREVENTION OF PARASITIC DISEASES AND METHOD OF PRODUCTION THEREOF
  申请人：Institut de Recherche pour le Developpement (I.R.D.)

  公开号：EP3022173B1

  公开（公告）日：2019-02-20
• NEW COMPOUNDS FOR THE TREATMENT AND/OR PREVENTION OF PARASITIC DISEASES AND METHOD OF PRODUCTION OF THEREOF
  申请人：INSTITUT DE RECHERCHE POUR LE DEVELOPPEMENT (I.R.D.)

  公开号：US20160168084A1

  公开（公告）日：2016-06-16

  Disclosed are new compounds for treating, preventing or inhibiting a parasitic disease, preferably toxoplasmosis in a subject, the method for preparing thereof.
• Synthesis of aminophenylhydroxamate and aminobenzylhydroxamate derivatives and in vitro screening for antiparasitic and histone deacetylase inhibitory activity
  作者：C. Loeuillet、B. Touquet、B. Oury、N. Eddaikra、J.L. Pons、J.F. Guichou、G. Labesse、D. Sereno

  DOI：10.1016/j.ijpddr.2018.01.002

  日期：2018.4

  A series of aminophenylhydroxamates and aminobenzylhydroxamates were synthesized and screened for their antiparasitic activity against Leishmania, Trypanosoma, and Toxoplasma. Their anti-histone deacetylase (HDAC) potency was determined. Moderate to no antileishmanial or antitrypanosomal activity was found (IC50 > 10 mu M) that contrast with the highly efficient anti-Toxoplasma activity (IC50 < 1.0 mu M) of these compounds. The antiparasitic activity of the synthetized compounds correlates well with their HDAC inhibitory activity. The best-performing compound (named 363) express a high anti-HDAC6 inhibitory activity (IC50 of 0.045 +/- 0.015 mu M) a moderate cytotoxicity and a high anti-Toxoplasma activity in the range of known anti-Toxoplasma compounds (IC50 of 0.35-2.25 mu M). The calculated selectivity index (10-300 using different human cell lines) of the compound 363 makes it a lead compound for the future development of anti-Toxoplasma molecules.