3-(morpholinosulfonyl)benzoyl chloride | 854166-21-5

• 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: 3-(morpholinosulfonyl)benzoyl chloride
• 英文别名: 3-morpholin-4-ylsulfonylbenzoyl chloride
• CAS: 854166-21-5
• 化学式: C₁₁H₁₂ClNO₄S
• 分子量: 289.74
• InChiKey: FYSJSMVLMHWTOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(morpholinosulfonyl)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-(morpholinosulfonyl)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：

  3-(吗啉-4-基磺酰基)苯甲酸 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 3-(morpholinosulfonyl)benzoyl chloride
  参考文献：
  名称：

  具有抗血小板活性的新型嘌呤

  摘要：

  四种嘌呤 - 2,6 - 二胺，4a, b, 5a, b，十九种 N-（嘌呤 - 2 - 基）苯甲酰胺 6a - q, 7b 和一种 N-（嘌呤 - 2 - 基） -2 - 呋喃甲酰胺 8首次制备并测试它们对血小板聚集的抑制作用。6a、b、h、m、o、p六种化合物在Born试验中抑制胶原诱导的血小板聚集，IC50值在3～10μmol/L之间。ADP、PAF和肾上腺素被用作特异性聚集诱导剂来检查抗聚集活性的机制。观察到惊人的纳米摩尔级活动模式，6m、7b、8 甚至亚纳摩尔范围（6b）。化合物6b以IC50 = 0.45 nM（6m：3.5 nM；8：30 nM）抑制ADP诱导的血小板聚集。化合物 7b 显示出对诱导剂肾上腺素的拮抗作用，IC 50 = 1.8 nM (6o: 20 nM; 8: 30 nM)。

  DOI：

  10.1002/ardp.200500189

文献信息

• New Purines with Antiplatelet Activity
  作者：Katrin Märschenz、Klaus Rehse

  DOI：10.1002/ardp.200500189

  日期：2006.3

  collagen with IC50 values between 3 and 10 μmol/L in the Born test. ADP, PAF, and adrenaline were used as specific aggregation inducers to examine the mechanism of the anti‐aggregating activity. An astonishing pattern of activities in the nanomolar, with 6m, 7b, 8 and even subnanomolar range, with 6b, was observed. Compound 6b inhibited the platelet aggregation induced by ADP with an IC50 = 0.45 nM (6m: 3

  四种嘌呤 - 2,6 - 二胺，4a, b, 5a, b，十九种 N-（嘌呤 - 2 - 基）苯甲酰胺 6a - q, 7b 和一种 N-（嘌呤 - 2 - 基） -2 - 呋喃甲酰胺 8首次制备并测试它们对血小板聚集的抑制作用。6a、b、h、m、o、p六种化合物在Born试验中抑制胶原诱导的血小板聚集，IC50值在3～10μmol/L之间。ADP、PAF和肾上腺素被用作特异性聚集诱导剂来检查抗聚集活性的机制。观察到惊人的纳米摩尔级活动模式，6m、7b、8 甚至亚纳摩尔范围（6b）。化合物6b以IC50 = 0.45 nM（6m：3.5 nM；8：30 nM）抑制ADP诱导的血小板聚集。化合物 7b 显示出对诱导剂肾上腺素的拮抗作用，IC 50 = 1.8 nM (6o: 20 nM; 8: 30 nM)。
• SUBSTITUTED (E)-N'-(1-PHENYLETHYLIDENE)BENZOHYDRAZIDE ANALOGS AS HISTONE DEMETHYLASE INHIBITORS
  申请人：Vankayalapati Hariprasad

  公开号：US20140163017A1

  公开（公告）日：2014-06-12

  In one aspect, the invention relates to substituted (E)-N′-(1-phenylethylidene)benzohydrazide analogs, derivatives thereof, and related compounds, which are useful as inhibitors of lysine-specific histone demethylase, including LSD1; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds and compositions to treat disorders associated with dysfunction of the LSD1. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在一个方面，本发明涉及取代的(E)-N′-(1-苯乙烯基)苯肼类似物、其衍生物和相关化合物，它们可用作赖氨酸特异性组蛋白去甲基化酶，包括LSD1的抑制剂；制备这些化合物的合成方法；含有这些化合物的制药组合物；以及使用这些化合物和组合物治疗与LSD1功能障碍相关的疾病的方法。本摘要旨在作为搜索特定技术领域的扫描工具，不旨在限制本发明。
• Substituted (E)-N′-(1-phenylethylidene)benzohydrazide analogs as histone demethylase inhibitors
  申请人：Vankayalapati Hariprasad

  公开号：US09266838B2

  公开（公告）日：2016-02-23

  In one aspect, the invention relates to substituted (E)-N′-(1-phenylethylidene)benzohydrazide analogs, derivatives thereof, and related compounds, which are useful as inhibitors of lysine-specific histone demethylase, including LSD1; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds and compositions to treat disorders associated with dysfunction of the LSD1. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在一个方面，本发明涉及取代的(E)-N′-(1-苯乙烯基)苯甲酰肼类似物、其衍生物和相关化合物，它们可用作赖氨酸特异性组蛋白去甲基化酶，包括LSD1的抑制剂；制备这些化合物的合成方法；包含这些化合物的制药组合物；以及使用这些化合物和组合物治疗与LSD1功能障碍相关的疾病的方法。本摘要旨在作为特定领域的搜索工具，不限制本发明。
• Synthesis of (bis)Sulfonic acid, (bis)Benzamides as follicle-Stimulating hormone (FSH) antagonists
  作者：Jay Wrobel、Daniel Green、James Jetter、Wenling Kao、John Rogers、M Claudia Pérez、Jill Hardenburg、Darlene C Deecher、Francisco J López、Brian J Arey、Emily S Shen

  DOI：10.1016/s0968-0896(01)00324-8

  日期：2002.3

  Screening efforts identified (bis)sulfonic acid. (bis)benzamides (1-3) as compounds that interact with the follicle stimulating-hormone receptor (FSHR) and inhibit FSH-stimulated CAMP accumulation with IC50 values in the low micromolar range. Structure-activity relationship studies using novel analogues of 1-3 revealed that two phenylsulfonic acid moieties were necessary for activity and that the carbon-carbon double bond of the stilbene sub-series was the optimum spacer connecting these groups. Selected analogues (2, 14, and 50) were also able to block FSHR-dependent estradiol production in rat primary ovarian granulosa cells and progesterone secretion in a clonal mouse adrenal Y1 cell line. IC50 values for these compounds in these assays were in the low micromolar range. Optimization of the benzoic acid side chains of 1-3 led to gains in selectivity versus activity at the thyroid stimulating hormone (TSH) receptor (TSHR). For instance, while stilbene (bis)sulfonic acid congener 2 was only 10-fold selective for FSHR over TSHR, analogue 50 with an IC50 value of 0.9 muM in the FSHR-cAMP assay was essentially inactive at 30muM in the TSHR-cAMP assay. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Correlation of carboxylic acid pKa to protein binding and antibacterial activity of a novel class of bacterial translation inhibitors
  作者：Cory M. Stiff、Min Zhong、Ronald W. Sarver、Hua Gao、Andrea M. Ho、Michael T. Sweeney、Gary E. Zurenko、Donna L. Romero

  DOI：10.1016/j.bmcl.2007.05.006

  日期：2007.10

  Previously we reported the discovery and initial optimization of a novel anthranilic acid derived class of antibacterial agents which suffered from extensive protein binding. This report describes efforts directed toward understanding the relationship of the acidity of the carboxylic acid with the extent of protein binding. The pK(a) of the acid was modified via the synthesis of a number of anthranilic acid analogs which vary the aromatic ring substituent at the 4-position. The pK(a) and HSA binding constants have been determined for each of the analogs. Our results indicate a correlation between pK(a) and HSA K-d. The physical properties and antibacterial activities will be discussed as well as how these results help address the protein binding issue with this series of compounds. (C) 2007 Published by Elsevier Ltd.