N-(4-fluorophenyl)-2-mercaptobenzamide | 628702-17-0

• 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-(4-fluorophenyl)-2-mercaptobenzamide
• 英文别名: N-(4-Fluorophenyl)-2-sulfanylbenzamide
• CAS: 628702-17-0
• 化学式: C₁₃H₁₀FNOS
• mdl: MFCD18824644
• 分子量: 247.293
• InChiKey: SEJKVQMTTRLJKL-UHFFFAOYSA-N

物化性质

• 熔点：
  129.5-131 °C
• 沸点：
  305.4±27.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-fluorophenyl)-2-mercaptobenzamide 在 molybdenum hexacarbonyl 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以80%的产率得到N-(4-氟苯基)苯甲酰胺
  参考文献：
  名称：

  钼介导的硫醇和二硫化物脱硫

  摘要：

  我们已经成功地实现了六羰基钼 [Mo(CO)6] 介导的硫醇和二硫化物的脱硫。在该反应中，芳基、苄基、伯和仲烷基硫醇的巯基 (SH) 巯基以及二硫化物的 S-S 单键可以被去除。该反应具有高官能团耐受性且不受空间位阻影响。丙酮-d 6 反应的结果表明，硫醇和二硫化物脱硫中的氢源分别是巯基和丙酮（溶剂）的氢原子，脱硫通过形成一种有机钼物种。

  DOI：

  10.1055/s-0034-1378315
• 作为产物：
  描述：

  4-氟苯胺 、 硫代水杨酸甲酯 在 三甲基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 12.5h， 以82%的产率得到N-(4-fluorophenyl)-2-mercaptobenzamide
  参考文献：
  名称：

  氧化脱氢环化形成铜催化的分子内NS键

  摘要：

  描述了铜通过分子内脱氢环化反应合成苯并[ d ]异噻唑-3（2 H）-酮和N-酰基-苯并噻唑烷的方法。在该反应中，通过NH / S-H偶联形成一个新的氮-硫（NS）键。本反应具有较高的官能团耐受性，并得到以克为单位的产物。该方法促进了双环化，从而允许合成药物中间体。

  DOI：

  10.1021/jo401056g

文献信息

• Double 1,4-addition of (thio)salicylamides/thiosalicylic acids with propiolate derivatives: a direct, general synthesis of diverse heterocyclic scaffolds
  作者：Hui-Hong Wang、Tao Shi、Wei-Wei Gao、Hong-Hua Zhang、Yong-Qiang Wang、Jun-Fang Li、Yong-Sheng Hou、Jin-Hong Chen、Xue Peng、Zhen Wang

  DOI：10.1039/c7ob02101a

  日期：——

  ring-closure procedure to prepare a range of diverse heterocycles has been developed. In this transformation, a variety of substituted (thio)salicylamides and thiosalicylic acids occured double 1, 4-additions reaction with propiolate derivatives in the presence of inorganic base (K3PO4), as a result, benzothiazinones, benzoxazinones and benzoxathiinones were prepared in good to excellent yields respectively

  已经开发了一种简单实用的闭环方法来制备一系列不同的杂环。在该转化过程中，在无机碱（K3PO4）存在下，各种取代的（硫代）水杨酰胺和硫代水杨酸与丙酸酯衍生物发生了双1、4加成反应，结果制备了苯并噻嗪酮，苯并恶嗪酮和苯并噻吩并酮即使以克为单位，也具有出色的产量。另外，还成功地进行了向更复杂结构和奥昔康药物类似物的进一步转化。
• Antimycobacterial and Antifungal Isosters of Salicylamides
  作者：Karel Waisser、Milan Pešina、Pavel Holý、Milan Pour、Otakar Bureš、Jiší Kuneš、Všra Klimešová、Vladimír Buchta、Petra Kubanová、Jarmila Kaustová

  DOI：10.1002/ardp.200300725

  日期：2003.8

  Microsporum gypseum. Structure‐activity relationships of antimycobacterial activity and antifungal activity against T. mentagrophytes and M. gypseum were analyzed by the Free‐Wilson method. An increase in antimycobacterial activity was observed only for the sulfanylbenzoic acid derivatives, especially those with the benzyl moiety. The antifungal activity was not significant.

  合成了一组 40 种 3-羟基吡啶甲酸和 2-硫烷基苯甲酸的衍生物，与水杨酰苯胺等排。评估了这些化合物对结核分枝杆菌、堪萨斯分枝杆菌和鸟分枝杆菌、白色念珠菌、热带念珠菌、克柔念珠菌、光滑念珠菌、细孢子菌、烟曲霉、棒状孢霉和毛癣菌的体外活性。采用Free-Wilson法分析了须癣菌和石膏分枝杆菌的抗分枝杆菌活性和抗真菌活性的构效关系。仅观察到硫烷基苯甲酸衍生物的抗分枝杆菌活性增加，尤其是那些具有苄基部分的衍生物。抗真菌活性不显着。
• Copper-Catalyzed Intramolecular N–S Bond Formation by Oxidative Dehydrogenative Cyclization
  作者：Zhen Wang、Yoichiro Kuninobu、Motomu Kanai

  DOI：10.1021/jo401056g

  日期：2013.7.19

  Copper-catalyzed synthesis of benzo[d]isothiazol-3(2H)-ones and N-acyl-benzothiazetidine by intramolecular dehydrogenative cyclization is described. In this reaction, a new nitrogen–sulfur (N–S) bond is formed by N–H/S–H coupling. The present reaction has high functional group tolerance and gives products in gram scale. This method promotes double cyclization, allowing for synthesis of a drug intermediate

  描述了铜通过分子内脱氢环化反应合成苯并[ d ]异噻唑-3（2 H）-酮和N-酰基-苯并噻唑烷的方法。在该反应中，通过NH / S-H偶联形成一个新的氮-硫（NS）键。本反应具有较高的官能团耐受性，并得到以克为单位的产物。该方法促进了双环化，从而允许合成药物中间体。
• Design, synthesis and evaluation of benzoisothiazolones as selective inhibitors of PHOSPHO1
  作者：Yalda Bravo、Peter Teriete、Raveendra-Panickar Dhanya、Russell Dahl、Pooi San Lee、Tina Kiffer-Moreira、Santhi Reddy Ganji、Eduard Sergienko、Layton H. Smith、Colin Farquharson、José Luis Millán、Nicholas D.P. Cosford

  DOI：10.1016/j.bmcl.2014.07.013

  日期：2014.9

  We report the discovery and characterization of a series of benzoisothiazolone inhibitors of PHOSPHO1, a newly identified soluble phosphatase implicated in skeletal mineralization and soft tissue ossification abnormalities. High-throughput screening (HTS) of a small molecule library led to the identification of benzoisothiazolones as potent and selective inhibitors of PHOSPHO1. Critical structural requirements for activity were determined, and the compounds were subsequently derivatized and measured for in vitro activity and ADME parameters including metabolic stability and permeability. On the basis of its overall profile the benzoisothiazolone analogue 2q was selected as MLPCN probe ML086.
• Exploring the Structural Requirements for Inhibition of the Ubiquitin E3 Ligase Breast Cancer Associated Protein 2 (BCA2) as a Treatment for Breast Cancer
  作者：Ghali Brahemi、Fathima R. Kona、Annalisa Fiasella、Daniela Buac、Jitka Soukupová、Andrea Brancale、Angelika M. Burger、Andrew D. Westwell

  DOI：10.1021/jm901757t

  日期：2010.4.8

  The zinc-ejecting aldehyde dehydrogenase (A LDH) inhibitory drug disulfiram (DS F) was found to be a breast cancer-associated protein 2 (BCA2) inhibitor with potent antitumor activity. We herein describe our work in the synthesis and evaluation of new series of zinc-affinic molecules to explore the structural requirements for selective BCA2-inhibitory antitumor activity. An N(C=S)S-S motif was found to be required, based on selective activity in BCA2-expressing breast cancer cell lines and against recombinant BCA2 protein. Notably, the DSF analogs (3a and 3c) and dithio(peroxo)thioate compounds (5d and 5f) were found to have potent activity (submicromolar IC(50)) in BCA2 positive MCF-7 and T47D cells but were inactive (IC(50)> 10 mu M) in BCA2 negative M DA-MB-231 breast cancer cells and the normal breast epithelial cell line MCF10A. Testing in the isogenic BCA2 +ve M DA-MB-231/ER cell line restored antitumor activity for compounds that were inactive in the BCA2 -ve MDA-MB-231 cell line. In contrast, structurally related dithiocarbamates and benzisothiazolones (lacking the disulfide bond) were all inactive. Compounds 5d and 5f were additionally found to lack ALDH-inhibitory activity, suggestive of selective E3 ligase-inhibitory activity and worthy of further development.