3-carbomethoxy-4-thiochromanone | 6125-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: 3-carbomethoxy-4-thiochromanone
• 英文别名: 3-methoxycarbonylchroman-4-one；methyl 4-oxothiochroman-3-carboxylate；methyl 4-oxothiochromane-3-carboxylate；4-oxo-thiochroman-3-carboxylic acid methyl ester；methyl-3,4-dihydro-4-oxo-2H-1-benzothiopyran-3-carboxylate；4Oxo-3-thiochromancarboxylic acid methyl ester；methyl 4-oxo-2,3-dihydrothiochromene-3-carboxylate
• CAS: 6125-48-0
• 化学式: C₁₁H₁₀O₃S
• 分子量: 222.265
• InChiKey: XBZZDZFHFUDIQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  158-160 °C
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-carbomethoxy-4-thiochromanone 在 溶剂黄146 、 肼 作用下， 反应 10.0h， 以42%的产率得到1,4-Dihydro-2H-thiochromeno[4,3-c]pyrazol-3-one
  参考文献：
  名称：

  Novel immunosuppressive agents. Potent immunological activity of some benzothiopyrano[4,3-c]pyrazol-3-ones

  摘要：

  A unique class of immunosuppressive agents has been found be the use of a mouse model of immunity. A number of bensothiopyrano[4,3-c]pyrazol-3-ones are potent inhibitors of both the humoral and cellular immune response developed in mice in response to El4 tumor cells. These compounds exhibit a selectivity for inhibiting the humoral response. Structure-activity relationships and Hansch analyses of data from the mouse model are discussed. One of the most potent compounds, 2-(4'-chlorophenyl)bensothiopyrano[4,3-c]pyrazol-3-one (1, CP-17 193), exhibits ED50 values for inhibiting the humoral and cellular responses in the range of 0.5-2 mg/kg, po, in the mouse model and also inhibits antibody production to several other antigens and prolongs skin graft survival in mice. These compounds are shown in several ways to be distinct from the lymphocytotoxic drugs cyclophosphamide and azathioprine.

  DOI：

  10.1021/jm00139a012
• 作为产物：
  描述：

  硫代色满-4-酮 、 氰基甲酸甲酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 3-carbomethoxy-4-thiochromanone
  参考文献：
  名称：

  Novel immunomodulating compounds

  摘要：

  本发明涉及一种新颖的杂环化合物，一种包含该化合物的药物组合物，以及该化合物在临床治疗可能受益于免疫调节的医疗状况的方法和用途，例如类风湿关节炎、多发性硬化症、糖尿病、哮喘、移植、系统性红斑狼疮和牛皮癣。更具体地，本发明涉及一种新颖的杂环化合物，这些化合物是CD80拮抗剂，能够抑制CD80和CD28之间的相互作用。描述了一种筛选化合物的方法，用于评估它们抑制免疫能力的能力，即抑制免疫能力的人类细胞内的配体诱导的共刺激受体内化途径。在至少一种试验化合物存在的条件下，孵育这些免疫能力的人类细胞，能够诱导共刺激受体内化，并确定抑制配体诱导的共刺激受体内化。还描述了一种用于此类方法的试剂盒，以及一种能够阻断配体诱导受体下调的免疫调节药物。

  公开号：

  US20030022913A1

文献信息

• Air- and Light-Stable <i>S</i>-(Difluoromethyl)sulfonium Salts: <i>C</i>-Selective Electrophilic Difluoromethylation of β-Ketoesters and Malonates
  作者：Sheng-Le Lu、Xin Li、Wen-Bing Qin、Jian-Jian Liu、Yi-Yong Huang、Henry N. C. Wong、Guo-Kai Liu

  DOI：10.1021/acs.orglett.8b03067

  日期：2018.11.2

  Air- and light-stable electrophilic difluoromethylating reagents, S-(difluoromethyl)-S-phenyl-S-(2,4,6-trialkoxyphenyl) sulfonium salts were successfully developed, and the introduction of intramolecular hydrogen bonds plays a crucial role for the stabilities and reactivities of these reagents. C-selective difluoromethylation of a broad range of β-ketoesters and malonates proceeded smoothly under mild

  空气和光稳定的亲电子二氟甲基化试剂，S-（二氟甲基）-S-苯基-S-（2,4,6-三烷氧基苯基）salts盐已成功开发，并且分子内氢键的引入对于该化合物起着至关重要的作用。这些试剂的稳定性和反应性。在温和的反应条件下，各种β-酮酸酯和丙二酸酯的C选择性二氟甲基化反应平稳进行，从而以良好的C / O区域选择性提供了良好至优异的收率。
• Bench‐Stable <i>S</i> ‐(Monofluoromethyl)sulfonium Salts: Highly Efficient <i>C</i> ‐ and <i>O</i> ‐Regioselective Monofluoromethylation of 1,3‐Dicarbonyl Compounds
  作者：Wen‐Bing Qin、Jian‐Jian Liu、Zhongyan Huang、Xin Li、Wei Xiong、Jia‐Yi Chen、Guo‐Kai Liu

  DOI：10.1002/ejoc.202000998

  日期：2020.9.30

  Novel bench‐stable S‐(monofluoromethyl)‐S‐phenyl‐S‐(2,4,6‐trialkoxyphenyl)sulfonium salts were readily prepared for C‐ and O‐regioselective monofluoromethylation of 1,3‐dicarbonyl compounds in good to excellent yields under mild reaction conditions.

  新型稳定的S-（单氟甲基）-S-苯基-S-（2,4,6-三烷氧基苯基）ulf盐易于制备，可用于1,3-二羰基化合物的C和O区域选择性单氟甲基化在温和的反应条件下。
• Synthesis and Evaluation of Antileishmanial and Cytotoxic Activity of Benzothiopyrane Derivatives
  作者：Cristian Ortiz、Fernando Echeverri、Sara Robledo、Daniela Lanari、Massimo Curini、Wiston Quiñones、Esteban Vargas

  DOI：10.3390/molecules25040800

  日期：——

  In continuation of our efforts to identify promising antileishmanial agents based on the chroman scaffold, we synthesized several substituted 2H-thiochroman derivatives, including thiochromenes, thichromanones and hydrazones substituted in C-2 or C-3 with carbonyl or carboxyl groups. Thirty-two compounds were thus obtained, characterized, and evaluated against intracellular amastigotes of Leishmania

  为了继续努力确定基于色满支架的有希望的抗利什曼试剂，我们合成了几种取代的 2H-硫色满衍生物，包括在 C-2 或 C-3 中被羰基或羧基取代的硫色烯、硫色满酮和腙。因此获得、表征和评估了 32 种化合物，并针对 Leishmania (V) panamensis 的细胞内无鞭毛体进行了评估。12 种化合物具有活性，EC50 值低于 40 µM，但只有四种化合物显示出最高的抗利什曼原虫活性，EC50 值低于 10 µM；这些所有化合物都具有良好的选择性指数 > 2.6。尽管两种活性化合物是硫色素，但由于每种活性化合物具有不同的取代模式，因此未检测到明确的构效关系。
• Immunomodulatory compounds
  申请人：ACTIVE BIOTECH AB

  公开号：US20040116461A1

  公开（公告）日：2004-06-17

  The present invention relates to novel heterocyclic compounds, to methods for their preparation, to compositions containing them, and to methods and use for clinical treatment of medical conditions which may benefit from immunomodulation, including rheumatoid arthritis, multiple sclerosis, diabetes, asthma, transplantation, systemic lupus erythematosis and psoriasis. More particularly the present invention relates to novel heterocyclic compounds, which are CD80 antagonists capable of inhibiting the interactions between CD80 and CD28.

  本发明涉及新颖的杂环化合物，其制备方法，含有它们的组合物，以及用于临床治疗可能受益于免疫调节的医疗状况的方法和用途，包括类风湿关节炎、多发性硬化症、糖尿病、哮喘、移植、系统性红斑狼疮和牛皮癣。更具体地，本发明涉及新颖的杂环化合物，它们是CD80拮抗剂，能够抑制CD80和CD28之间的相互作用。
• Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of β-ketoesters: An Unusual Counterion Effect
  作者：Barry M. Trost、Benjamin Schäffner、Maksim Osipov、Donna A. A. Wilton

  DOI：10.1002/anie.201007803

  日期：2011.4.4

  allyl chloroformate and their β‐ketoesters by using the same catalyst system (see scheme; dba=dibenzylideneacetone, 1,2‐DCE=1,2‐dichloroethane, THF=tetrahydrofuran). The details of this remarkable effect were investigated by performing scavenging experiments and a variety of substrates were successfully used in the procedure.

  买一送一：在相同的催化剂体系下，氯甲酸烯丙酯及其β-酮酸酯可以通过一锅法获得四氢萘酮和茚满酮衍生物的对映异构体（请参阅方案； dba =二苄叉基丙酮，1,2-DCE = 1,2-二氯乙烷，THF =四氢呋喃）。通过执行清除实验研究了这种显着效果的细节，并成功地在该过程中使用了多种基材。