m-dimethylamino-sulfonyl-benzoyl chloride | 188674-88-6

• 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: m-dimethylamino-sulfonyl-benzoyl chloride
• 英文别名: 3-(N,N-dimethylsulfamoyl)benzoyl chloride；3-[(dimethylamino)sulfonyl]benzoyl chloride；3-Dimethylsulfamoyl-benzoyl chloride；3-(dimethylsulfamoyl)benzoyl chloride
• CAS: 188674-88-6
• 化学式: C₉H₁₀ClNO₃S
• 分子量: 247.702
• InChiKey: NIGQHLJUFNFGKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  m-dimethylamino-sulfonyl-benzoyl chloride 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 2-(3-(N,N-dimethylsulfamoyl)benzamido)benzoic acid
  参考文献：
  名称：

  Structure Optimization of 2-Benzamidobenzoic Acids as PqsD Inhibitors for Pseudomonas aeruginosa Infections and Elucidation of Binding Mode by SPR, STD NMR, and Molecular Docking

  摘要：

  Pseudomonas aeruginosa employs a characteristic pqs quorum sensing (QS) system that functions via the signal molecules PQS and its precursor HHQ, They control the production of a number of virulence factors and biofilm formation. Recently, we have shown that sulfonamide substituted 2-benzamidobenzoic acids, which are known FabH inhibitors, are also able to inhibit PqsD, the enzyme catalyzing the last and key step in the biosynthesis of HHQ, Here, we describe the further optimization and characterization of this class of compounds as PqsD inhibitors. Structural modifications showed that both the carboxylic acid ortho to the amide and 3'-sulfonamide are essential for binding. Introduction of substituents in the anthranilic part of the molecule resulted in compounds with IC50 values in the low micromolar range. Binding mode investigations by SPR with wild-type and mutated PqsD revealed that this compound class does not bind into the active center of PqsD but in the ACoA channel, preventing the substrate from accessing the active site. This binding mode was further confirmed by docking studies and STD NMR.

  DOI：

  10.1021/jm4006302
• 作为产物：
  描述：

  N,N-二甲基- 3-羧基苯磺酰胺 在 氯化亚砜 作用下， 生成 m-dimethylamino-sulfonyl-benzoyl chloride
  参考文献：
  名称：

  脲-四氢苯并氧杂蒽的羧酸受体

  摘要：

  已经基于顺式四氢苯并氧杂蒽骨架制备了羧酸的氢键受体。这些化合物之一的X射线衍射研究表明，该裂口适合与水分子的氧建立牢固的线性氢键。与客体仅设置三个H键的复合物没有显示出与氨基酸衍生物的手性识别。然而，受体的适当官能化提供了与某些氨基酸衍生物的第四H键，在这种情况下导致显着的对映选择性络合。

  DOI：

  10.1016/j.tet.2004.03.015

文献信息

• Fluoride ion-induced cyclization of o-[bis(trimethylsilyl)methyl]-N-acylbenzamide derivatives. New efficient synthesis of 2,3-differentially substituted 1(2H)-isoquinolones
  作者：Axel Couture、Hélène Cornet、Eric Deniau、Pierre Grandclaudon、Stéphane Lebrun

  DOI：10.1039/a605077h

  日期：——

  A wide variety of 2-alkyl-3-alkyl, -3-aryl and -3-heteroaryl-1(2H)-isoquinolones have been obtained by fluoride ion-induced intramolecular alkenation of o-[bis(trimethylsilyl)methyl]-N -acylbenzamide derivatives.

  已经通过氟离子诱导的烯化反应，获得了多种2-烷基-3-烷基、3-芳基和3-杂芳基-1(2H)-异喹啉酮衍生物，这些衍生物来自于o-[双(三甲基硅基)甲基]-N-酰基苯胺衍生物。
• Urea-tetrahydrobenzoxanthene receptors for carboxylic acids
  作者：Ana I Oliva、Luis Simón、Francisco M Muñiz、Francisca Sanz、Joaquı́n R Morán

  DOI：10.1016/j.tet.2004.03.015

  日期：2004.4

  Hydrogen-bonding receptors for carboxylic acids have been prepared based on a cis tetrahydrobenzoxanthene skeleton. X-ray diffraction study of one of these compounds revealed that the cleft is suitable for establishing strong linear hydrogen bonds with the oxygen of a water molecule. Complexes that set only three H-bonds with the guests showed no chiral recognition with amino acid derivatives. However, suitable

  已经基于顺式四氢苯并氧杂蒽骨架制备了羧酸的氢键受体。这些化合物之一的X射线衍射研究表明，该裂口适合与水分子的氧建立牢固的线性氢键。与客体仅设置三个H键的复合物没有显示出与氨基酸衍生物的手性识别。然而，受体的适当官能化提供了与某些氨基酸衍生物的第四H键，在这种情况下导致显着的对映选择性络合。
• Propane-1,3-dione derivative or salt thereof
  申请人：Astellas Pharma Inc.

  公开号：US07960562B2

  公开（公告）日：2011-06-14

  It is intended to provide a compound useful as a GnRH receptor antagonist. The inventors further investigated propane-1,3-dione derivatives. As a result, they confirmed that a compound having a benzene ring or a thiophene ring substituted with a group represented by —SO2—R3 in a propane-1,3-dione derivative having 2-(1,3-dihydro-2H-benzimidazol-2-ylidene) has an excellent GnRH receptor antagonistic effect and accomplished the present invention. Because the compound of the present invention has a potent GnRH receptor antagonistic effect, it is useful for the treatment of sex hormone-dependent diseases, particularly GnRH-related diseases. Further, because the compound of the present invention has an excellent metabolic stability in human and few drug interactions, therefore it has preferable characteristics as a pharmaceutical used for the above-mentioned diseases.

  本发明旨在提供一种作为GnRH受体拮抗剂有用的复合物。发明人进一步研究了丙酮酸1,3-二酮衍生物。结果，他们确认，在具有2-(1,3-二氢-2H-苯并咪唑-2-基亚胺基)的丙酮酸1,3-二酮衍生物中，苯环或噻吩环取代为—SO2—R3基团的化合物具有出色的GnRH受体拮抗效果，并完成了本发明。由于本发明化合物具有强效的GnRH受体拮抗作用，因此对于治疗性激素依赖性疾病，特别是GnRH相关疾病非常有用。此外，由于本发明化合物在人体内具有出色的代谢稳定性和少量药物相互作用，因此具有作为上述疾病用药物的优良特性。
• Propane-1,3-Dione Derivative or Salt Thereof
  申请人：Hirano Masaaki

  公开号：US20090181964A1

  公开（公告）日：2009-07-16

  It is intended to provide a compound useful as a GnRH receptor antagonist. The inventors further investigated propane-1,3-dione derivatives. As a result, they confirmed that a compound having a benzene ring or a thiophene ring substituted with a group represented by —SO 2 —R 3 in a propane-1,3-dione derivative having 2-(1,3-dihydro-2H-benzimidazol-2-ylidene) has an excellent GnRH receptor antagonistic effect and accomplished the present invention. Because the compound of the present invention has a potent GnRH receptor antagonistic effect, it is useful for the treatment of sex hormone-dependent diseases, particularly GnRH-related diseases. Further, because the compound of the present invention has an excellent metabolic stability in human and few drug interactions, therefore it has preferable characteristics as a pharmaceutical used for the above-mentioned diseases.

  本发明旨在提供一种作为GnRH受体拮抗剂有用的化合物。发明人进一步研究了丙酮酸1,3-二酮衍生物。结果，他们证实，在2-(1,3-二氢-2H-苯并咪唑-2-基亚胺)具有苯环或噻吩环的衍生物中，取代为—SO2—R3基团的化合物具有出色的GnRH受体拮抗作用，并完成了本发明。由于本发明的化合物具有强效的GnRH受体拮抗作用，因此对于治疗性激素依赖性疾病，特别是GnRH相关疾病非常有用。此外，由于本发明的化合物在人体内具有出色的代谢稳定性和较少的药物相互作用，因此作为用于上述疾病的药物具有良好的特性。
• PROPANE-1,3-DION DERIVATIVE OR SALT THEREOF
  申请人：Astellas Pharma Inc.

  公开号：EP1864976B1

  公开（公告）日：2012-10-10