2,4-dichloro-5-(morpholinosulfonyl)benzoic acid | 292644-05-4

• 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: 2,4-dichloro-5-(morpholinosulfonyl)benzoic acid
• 英文别名: 2,4-Dichloro-5-(morpholin-4-ylsulfonyl)benzoic acid；2,4-dichloro-5-morpholin-4-ylsulfonylbenzoic acid
• CAS: 292644-05-4
• 化学式: C₁₁H₁₁Cl₂NO₅S
• mdl: MFCD00739271
• 分子量: 340.184
• InChiKey: WMSHTRGJCJVTQA-UHFFFAOYSA-N

物化性质

• 沸点：
  535.6±60.0 °C(Predicted)
• 密度：
  1.602±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-5-(morpholinosulfonyl)benzoic acid 在 吡啶 、 草酰氯 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 4-((3-cyano-2-(2,4-dichloro-5-(morpholinosulfonyl)benzamido)-4,5-dihydrothieno[2,3-c]pyridin-6(7H)-yl)methyl)benzoic acid
  参考文献：
  名称：

  Structure–activity relationships of new cyanothiophene inhibitors of the essential peptidoglycan biosynthesis enzyme MurF

  摘要：

  Peptidoglycan is an essential component of the bacterial cell wall, and enzymes involved in its biosynthesis represent validated targets for antibacterial drug discovery. MurF catalyzes the final intracellular peptidoglycan biosynthesis step: the addition of D-Ala-D-Ala to the nucleotide precursor UDP-MurNAc-L-Ala-gamma-D-Glu-meso-DAP (or L-Lys). As MurF has no human counterpart, it represents an attractive target for the development of new antibacterial drugs. Using recently published cyanothiophene inhibitors of MurF from Streptococcus pneumoniae as a starting point, we designed and synthesized a series of structurally related derivatives and investigated their inhibition of MurF enzymes from different bacterial species. Systematic structural modifications of the parent compounds resulted in a series of nanomolar inhibitors of MurF from S. pneumoniae and micromolar inhibitors of MurF from Escherichia coli and Staphylococcus aureus. Some of the inhibitors also show antibacterial activity against S. pneumoniae R6. These findings, together with two new co-crystal structures, represent an excellent starting point for further optimization toward effective novel antibacterials. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.013
• 作为产物：
  描述：

  2,4-二氯苯甲酸 在 氯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 2,4-dichloro-5-(morpholinosulfonyl)benzoic acid
  参考文献：
  名称：

  高效非羧酸自分泌运动因子抑制剂可减少黑色素瘤转移和乳腺癌干细胞的化疗耐药性

  摘要：

  自分泌运动因子（ATX，又名 ENPP2）是生物体液中脂质介质溶血磷脂酸 (LPA) 的主要来源。本研究报告了通过对计算机命中化合物3中的苯磺酰胺先导优化而衍生的 ATX 抑制剂。新的类似物提供了苯磺酰胺支架的全面构效关系，从而产生了一系列高效的 ATX 抑制剂。三种最有效的类似物（ 3a ，IC 50 ∼ 32 nM； 3b ，IC 50 ∼ 9 nM； 14 ，IC 50 ∼ 35 nM）在体外抑制 A2058 人黑色素瘤细胞的 ATX 依赖性侵袭。两种最有效的化合物3b和3f (IC 50 ∼ 84 nM) 对 ENPP6 和 ENPP7 缺乏抑制作用，但对 LPA 1 G 蛋白偶联受体具有弱拮抗作用。特别是，化合物3b可有效降低4T1乳腺癌干细胞样细胞对紫杉醇的体外化疗耐药性，并显着降低体内B16黑色素瘤转移。

  DOI：

  10.1021/acs.jmedchem.6b01270

文献信息

• Autotaxin inhibitors
  申请人：UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION

  公开号：US11124490B2

  公开（公告）日：2021-09-21

  The present disclosure provides novel ATX inhibitors, and pharmaceutical compositions comprising said inhibitors, as well as methods of treatment comprising administration of said inhibitors.

  本公开提供了新型 ATX 抑制剂和包含所述抑制剂的药物组合物，以及包括施用所述抑制剂的治疗方法。
• 2-Halobenzoyl chlorides in the synthesis of [1,3,4]thiadiazolo[3,2-a]quinazolin-5-one derivatives
  作者：R. M. Shlenev、A. V. Tarasov、S. I. Filimonov、P. A. Agat’ev、A. S. Danilova、K. Yu. Suponitskii

  DOI：10.1134/s1070428017120156

  日期：2017.12

  New nitro and sulfonamide derivatives of [1,3,4]thiadiazolo[3,2-a]quinazolin-5-one have been synthesized by cyclocondensation of 1,3,4-thiadiazol-2-amines with 2-halobenzoyl chlorides containing electronwithdrawing substituents in positions 3, 4, and 5. An improved procedure has been proposed for the preparation of intermediate 2-fluoro-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzamides containing a sulfamoyl group in the 5-position via selective acylation of 5-methyl-1,3,4-thiadiazol-2-amine with 5-chlorosulfonyl-2-fluorobenzoyl chloride, followed by sulfonylation of amines.
• [EN] AUTOTAXIN INHIBITORS<br/>[FR] INHIBITEURS DE L'AUTOTAXINE
  申请人：UNIV TENNESSEE RES FOUND

  公开号：WO2017210527A8

  公开（公告）日：2018-05-24
• SUBSTITUTED BENZOSULPHONAMIDES AS POTENTIATORS OF GLUTAMATE RECEPTORS
  申请人：AstraZeneca AB

  公开号：EP1615904B1

  公开（公告）日：2008-02-27
• AUTOTAXIN INHIBITORS
  申请人：UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION

  公开号：US20200317626A1

  公开（公告）日：2020-10-08

  The present disclosure provides novel ATX inhibitors, and pharmaceutical compositions comprising said inhibitors, as well as methods of treatment comprising administration of said inhibitors.