2,2'-dithiobis(5-methylbenzoic acid) | 13616-79-0

• 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: 2,2'-dithiobis(5-methylbenzoic acid)
• 英文别名: NSC 633231；2-[(2-Carboxy-4-methyl-phenyl)disulfanyl]-5-methyl-benzoic acid；2-[(2-carboxy-4-methylphenyl)disulfanyl]-5-methylbenzoic acid
• CAS: 13616-79-0
• 化学式: C₁₆H₁₄O₄S₂
• 分子量: 334.417
• InChiKey: VKTJWKGPIVTERS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2'-dithiobis(5-methylbenzoic acid) 在 sodium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 (R)-3-(2-Mercapto-5-methyl-benzoyl)-thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Thiazolothiazepine Inhibitors of HIV-1 Integrase

  摘要：

  A series of thiazolothiazepines were prepared and tested against purified human immunodeficiency virus type-1 integrase (HIV-1 IN) and viral replication. Structure-activity studies reveal that the compounds possessing the pentatomic moiety SC(O)CNC(O) with two carbonyl groups are in general more potent against purified IN than those containing only one carbonyl group. Substitution with electron-donating or -withdrawing groups did not enhance nor abolish potency against purified IN. By contrast, compounds with a naphthalene ring system showed enhanced potency, suggesting that a hydrophobic pocket in the IN active site might accommodate an aromatic system rather than a halogen. The position of sulfur in the thiazole ring appears important for potency against IN, as its replacement with an oxygen or carbon abolished activity. Further extension of the thiazole ring diminished potency. Compounds 1, 19, and 20 showed antiviral activity and inhibited IN within similar concentrations. These compounds inhibited IN when Mn2+ or Mg2+ was used as cofactor. None of these compounds showed detectable activities against HIV-1 reverse transcriptase, protease, virus attachment, or nucleocapsid protein zinc fingers. Therefore, thiazolothiazepines are potentially important lead compounds for development as inhibitors of IN and HIV replication.

  DOI：

  10.1021/jm990047z
• 作为产物：
  描述：

  2-氨基-5-甲基苯甲酸 在 盐酸 、 sodium nitrite 、 sodiumsulfide nonahydrate 、 sulfur 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 2,2'-dithiobis(5-methylbenzoic acid)
  参考文献：
  名称：

  卡宾催化获得硫色烯衍生物：通过从二硫化物中缓慢释放硫醇来控制反应途径

  摘要：

  含有二硫键的底物更稳定、气味更小，可用作有机合成中的苯硫酚前体。在此，开发了 α-溴烯醛和 2,2'-二硫代二苯甲醛之间的 N-杂环卡宾 (NHC) 催化反应。通过缓释策略，可以有效抑制副反应，获得收率高、光学纯度高的手性硫色烯衍生物。当探索所需产品在农药开发中的抗菌效用时，应用研究显示出令人鼓舞的结果。

  DOI：

  10.1021/acs.orglett.3c01414

文献信息

• 2,2'-Dithiodibenzamides as inhibitors of blood platelet aggregation.
  作者：KOJI YAMADA、HIDEKI NIINO、TAMOTSU HASHIMOTO、KATSUICHI SHUTO、NOBUHIRO NAKAMIZO、KAZUHIRO KUBO、TAKESHI ONO、AKIO NAKAMIZO、YO MURAYAMA

  DOI：10.1248/cpb.33.1214

  日期：——

  New and known analogues of 2, 2'-dithiodibenzamide were synthesized and tested for various pharmacological actions. This series of compounds was found to inhibit collagen-and adenosine 5'-diphosphate-induced aggregations of blood platelets. 2, 2'-Dithiobis (N-(2-hydroxypropyl) benzamide) (3, KF4939) was one of the most potent compounds in in vitro aggregometry studies. Compound 3 after oral administration also potently inhibited pulmonary thrombosis induced by arachidonic acid injection in mice and platelet aggregation ex vivo in rats. This compound may have clinical value as a new orally active inhibitor of platelet aggregation.

  新合成了已知的2,2'-二硫代二苯甲酰胺类似物，并测试了它们的多种药理作用。发现这一系列化合物能抑制胶原和5'-二磷酸腺苷诱导的血小板聚集。2,2'-二硫代双（N-(2-羟丙基)苯甲酰胺）（3，KF4939）是在体外聚集实验中活性最强的化合物之一。3号化合物经口服给药后，也能强效抑制小鼠由花生四烯酸注射引起的肺血栓形成和大鼠离体血小板聚集。该化合物可能具有临床价值，是一种新型口服活性血小板聚集抑制剂。
• Directed lithiation of arenethiols
  作者：Keith Smith、Charles M. Lindsay、Gareth J. Pritchard

  DOI：10.1021/ja00184a040

  日期：1989.1

  treatment with electrophiles provides a convenient approach to ortho-substituted arenethiol derivatives. The reactions with tetraisopropylthiuram disulfide provide direct access to the corresponding o-phenylene trithiocarbonates. Double lithiation of 4-methoxybenzenethiol results in C-lithiation adjacent to the methoxy group rather than the thiolate residue, indicating that methoxy is a more powerfully ortho-directing

  苯硫醇、甲苯-4-硫醇和 3,5-二甲基苯硫醇在四甲基乙二胺中被正丁基锂双重锂化（在硫和碳上）。C-锂化发生在硫醇基团的邻位，随后用亲电试剂处理为邻位取代的芳硫醇衍生物提供了方便的方法。与四异丙基秋兰姆二硫化物的反应可直接获得相应的邻亚苯基三硫代碳酸酯。4-甲氧基苯硫醇的双锂化导致与甲氧基相邻的 C-锂化而不是硫醇盐残基，表明甲氧基是此类金属化反应中更强大的邻位取代基。3-甲氧基苯硫醇在甲氧基和硫醇盐基团之间锂化。
• [EN] THIAZEPINE INHIBITORS OF HIV-1 INTEGRASE<br/>[FR] INHIBITEURS DE L'INTEGRASE DU VIH-1 A BASE DE THIAZEPINE
  申请人：US HEALTH

  公开号：WO2000068235A1

  公开（公告）日：2000-11-16

  The present invention discloses non-catechol compounds, such as thiazolothiazepines, and analogs and derivatives thereof, which are anti-integrase inhibitors. The compounds, which are useful as treatments for HIV disease, include compounds (I), (II), (III), or pharmaceutically acceptable salts thereof wherein A is thiazole, benzene, naphthalene, pyridine, pyrimidine, pyrazine, or quinoline; R is one or more of H, halogen, lower alkyl, lower alkoxy, NO2, lower ester or carboxylic acid; X-Y is CH2-S, S-CH2, CH2-O, CH2-S(O), S(O)-CH2, CH2-CH2, CH2-CH2-CH2, or CH2-CH2-CH2-CH2; R4 is H or hydroxy; R5 is H, phenyl, or alkylamine; W is S or O; and R6 is H, substituted or unsubstituted alkyl or amine; and Z is S, O, CH2, CH2CH2, or C=O.

  本发明揭示了非儿茶酚化合物，例如噻唑噻唑烷以及其类似物和衍生物，它们是抗整合酶抑制剂。这些化合物可用作治疗艾滋病的药物，包括化合物（I）、（II）、（III）或其药学上可接受的盐，其中A是噻唑，苯，萘，吡啶，嘧啶，吡嗪或喹啉；R是H，卤素，低碳基，低氧基，NO2，低酯或羧酸之一或多个；X-Y是CH2-S，S-CH2，CH2-O，CH2-S（O），S（O）-CH2，CH2-CH2，CH2-CH2-CH2或CH2-CH2-CH2-CH2；R4是H或羟基；R5是H，苯基或烷基胺；W是S或O；R6是H，取代或未取代的烷基或胺基；Z是S，O，CH2，CH2CH2或C=O。
• Compounds And Methods For Modulating Activity Of Calcium Release Channels
  申请人：Abramson Jonathan J.

  公开号：US20120101085A1

  公开（公告）日：2012-04-26

  The present teachings provide compounds of Formulae I and II: and pharmaceutically acceptable salts, hydrates, complexes, esters, and prodrugs thereof, wherein R 1 , R 1′ , R 2 , R 2′ , R 3 , R 3′ , and X are as defined herein. The present teachings also provide methods of making the compounds of formulae I and II, and methods of treating RyR-associated conditions, disorders, and diseases that include administering a therapeutically effective amount of a compound of formula I or II to a subject in need thereof. In addition, the present teachings relate to methods of reducing the open probability of a ryanodine receptor, and methods of reducing Ca 2+ release across a ryanodine receptor (e.g., into the cytoplasm of a cell), by contacting a compound of formula I or II with a ryanodine receptor.

  本发明提供了公式I和II的化合物：以及其药学上可接受的盐，水合物，配合物，酯和前药，其中R1，R1'，R2，R2'，R3，R3'和X如本文所定义。本发明还提供了制备公式I和II化合物的方法，以及治疗与RyR相关的疾病和疾病的方法，包括向需要的受体中投与公式I或II的化合物的治疗有效量。此外，本发明涉及通过将公式I或II的化合物与Ryanodine受体接触，以降低Ryanodine受体的开放概率和减少Ca2+释放（例如进入细胞质）的方法。
• The Preparation of Some 1-Alkylamino- and Dialkylaminoalkylaminothiaxanthones¹
  作者：S. Archer、C. M. Suter

  DOI：10.1021/ja01137a017

  日期：1952.9