4-allylthiobenzoic acid | 16195-39-4

• 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: 4-allylthiobenzoic acid
• 英文别名: 4-Prop-2-enylsulfanylbenzoic acid
• CAS: 16195-39-4
• 化学式: C₁₀H₁₀O₂S
• 分子量: 194.254
• InChiKey: IYCJGNRIKLNMRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-allylthiobenzoic acid 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以77%的产率得到4-allylsulfonylbenzoic acid
  参考文献：
  名称：

  Synthesis of (bis)Sulfonic acid, (bis)Benzamides as follicle-Stimulating hormone (FSH) antagonists

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(01)00324-8
• 作为产物：
  描述：

  二烯丙基二硫 、 4-巯基苯甲酸 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以61%的产率得到4-allylthiobenzoic acid
  参考文献：
  名称：

  二烯丙基硫化物对生物相关亲核试剂的烯丙基化和烷基化作用

  摘要：

  烯丙基硫是大蒜，洋葱和葱属其他成员中发现的具有生物活性的植物化学物质。在这里，我们表明二烯丙基二硫化物和二烯丙基三硫化物可以将烯丙基侧链转移至低分子量硫醇。关于该烯丙基转移反应，二烯丙基单硫化物是惰性的。另一方面，二烯丙基单硫醚的已知代谢物二烯丙基砜在生理相关条件下，通过异构化为亲电子乙烯基砜，将胺和硫醇烷基化。

  DOI：

  10.1021/acs.joc.6b02517

文献信息

• NEW NO-DONOR ASPIRIN DERIVATIVES
  申请人：Fruttero Roberta

  公开号：US20100210694A1

  公开（公告）日：2010-08-19

  The present invention refers to new NO-donors aspirin derivatives, a process for their preparation and pharmaceutical compositions containing them.

  本发明涉及一种新的NO供体阿司匹林衍生物，其制备方法和包含它们的药物组合物。
• [EN] NEW NO-DONOR ASPIRIN DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'ASPIRINE DONNEURS NO
  申请人：NICOX SA

  公开号：WO2009049961A3

  公开（公告）日：2009-06-25
• (Nitrooxyacyloxy)methyl Esters of Aspirin as Novel Nitric Oxide Releasing Aspirins
  作者：Loretta Lazzarato、Monica Donnola、Barbara Rolando、Konstantin Chegaev、Elisabetta Marini、Clara Cena、Antonella Di Stilo、Roberta Fruttero、Stefano Biondi、Ennio Ongini、Alberto Gasco

  DOI：10.1021/jm900587h

  日期：2009.8.27

  A series of (nitrooxyacyloxy)methyl esters of aspirin were synthesized and evaluated as new NO-donor aspirins. Different amounts of aspirin were released in serum from these products according to the nature of nitrooxyacyloxy moiety present, In the aromatic series, there is a rather good linear correlation between the amount of aspirin released and the potencies of the products in inhibiting platelet aggregation induced by collagen. Both the native compounds and the related nitrooxy-substituted acid metabolites were able to relax rat aorta strips precontracted with phenylephrine, in keeping with a NO-induced activation or the sGC as a mechanism that underlies the vasodilator effect. The products here described are new improved examples of NO-donor aspirins containing nitrooxy groups. They could represent all alternative to the use of aspirin ill a variety of clinical applications.
• 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.
• Allylation and Alkylation of Biologically Relevant Nucleophiles by Diallyl Sulfides
  作者：Kasi Viswanatharaju Ruddraraju、Zachary D. Parsons、Calvin D. Lewis、Kent S. Gates

  DOI：10.1021/acs.joc.6b02517

  日期：2017.1.6

  Allyl sulfides are bioactive phytochemicals found in garlic, onion, and other members of the genus Allium. Here we showed that diallyl disulfide and diallyl trisulfide can transfer allyl side chains to low molecular weight thiols. Diallyl monosulfide is inert with respect to this allyl transfer reaction. On the other hand, diallyl sulfone, a known metabolite of diallyl monosulfide, alkylates both amines

  烯丙基硫是大蒜，洋葱和葱属其他成员中发现的具有生物活性的植物化学物质。在这里，我们表明二烯丙基二硫化物和二烯丙基三硫化物可以将烯丙基侧链转移至低分子量硫醇。关于该烯丙基转移反应，二烯丙基单硫化物是惰性的。另一方面，二烯丙基单硫醚的已知代谢物二烯丙基砜在生理相关条件下，通过异构化为亲电子乙烯基砜，将胺和硫醇烷基化。