2-Methyl-3-methylthioindol | 40015-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-Methyl-3-methylthioindol
• 英文别名: 2-methyl-3-(methylthio)-1H-indole；2-methyl-3-(methylthio)indole；2-methyl-3-methylsulfanyl-1H-indole
• CAS: 40015-18-7
• 化学式: C₁₀H₁₁NS
• 分子量: 177.27
• InChiKey: QFNVKZVCOACGCV-UHFFFAOYSA-N

物化性质

• 沸点：
  107-110 °C(Press: 0.01 Torr)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Methyl-3-methylthioindol 在 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 0.5h， 以90%的产率得到2-甲基吲哚
  参考文献：
  名称：

  Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

  摘要：

  Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched. Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides. This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.

  DOI：

  10.1021/jo00100a045
• 作为产物：
  描述：

  (2-methyl-1H-indol-3-yl)-dimethylsulfonium chloride 以 水 、 甲苯 为溶剂， 生成 2-Methyl-3-methylthioindol
  参考文献：
  名称：

  Substituted indoles as alpha-1 agonists

  摘要：

  这项发明涉及α-1受体激动剂，优选为α-1A/L受体激动剂，其化学式如下：其中X为—S(O)n—或—C(O)—，A为C1-6烷基，芳基，杂环芳基，羟基烷基，或—(CH2)p—NRaRb，其他取代基如规范中所定义；或其各个异构体，消旋体或非消旋体混合物，或其药用盐或溶剂化合物。该发明还涉及含有这类化合物的药物组合物，以及它们作为治疗剂的使用方法和制备方法。

  公开号：

  US20030220319A1

文献信息

• Facile C–S Bond Cleavage of Aryl Sulfoxides Promoted by Brønsted Acid
  作者：Nuno Maulide、Bogdan R. Brutiu、Immo Klose

  DOI：10.1055/s-0040-1707109

  日期：——

  A method for the Bronsted acid promoted desulfination of aryl sulfoxides is presented. In the presence of a thiol, electron-rich sulfoxides undergo C–S bond cleavage to give the corresponding protodesulfinated arenes and disulfides.

  提出了一种布朗斯台德酸促进芳基亚砜脱硫的方法。在硫醇存在下，富含电子的亚砜会发生 C-S 键断裂，得到相应的原脱硫芳烃和二硫化物。
• Methylthiolation for Electron‐Rich Heteroarenes with DMSO‐TsCl
  作者：Lei‐Yang Zhang、Yue‐Hua Wu、Nai‐Xing Wang、Xue‐Wang Gao、Zhan Yan、Bao‐Cai Xu、Ning Liu、Bo‐Zhou Wang、Yalan Xing

  DOI：10.1002/ejoc.202100001

  日期：2021.3.5

  DMSO‐TsCl is developed for methylthiolation of various heteroarenes including pyrroles, furans, thiophenes and indoles under facile conditions. This protocol features scalable, general applicability of substrates and moderate to excellent yields. An acceptable mechanism is proposed, two of the key intermediates of proposed mechanism are detected by HRMS. Further applications of this method were also

  DMSO-TsCl是为在方便条件下将各种杂芳烃进行甲基硫醇化而开发的，包括吡咯，呋喃，噻吩和吲哚。该协议具有可扩展的基板通用性，并且具有中等至极好的产量。提出了一种可以接受的机制，该机制的两个关键中间体均通过HRMS进行检测。还对该方法进行了进一步的应用。
• [EN] INHIBITORS OF CYCLIN-DEPENDENT KINASE 12 (CDK12) AND USES THEREOF<br/>[FR] INHIBITEURS DE KINASE 12 DÉPENDANTE DES CYCLINES (CDK12) ET LEURS UTILISATIONS
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2018098361A1

  公开（公告）日：2018-05-31

  The present invention provides novel compounds of Formulae (I') and (II), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, prodrugs, and compositions thereof. Also provided are methods and kits involving the inventive compounds or compositions for treating and/or preventing proliferative diseases (e.g., cancers (e.g., leukemia, acute lymphoblastic leukemia, lymphoma, Burkitt's lymphoma, melanoma, multiple myeloma, breast cancer, Ewing's sarcoma, osteosarcoma, brain cancer, ovarian cancer, neuroblastoma, lung cancer, colorectal cancer), benign neoplasms, diseases associated with angiogenesis, inflammatory diseases, autoinflammatory diseases, and autoimmune diseases) in a subject. Treatment of a subject with a proliferative disease using a compound or composition of the invention may inhibit the aberrant activity of a kinase, such as a cyclin-dependent kinase (CDK) (e.g., CDK12), and therefore, induce cellular apoptosis and/or inhibit transcription in the subject.

  本发明提供了式(I')和(II)的新化合物，以及这些化合物的药学可接受的盐、溶剂合物、水合物、多晶形态、共晶体、互变异构体、立体异构体、同位素标记衍生物、前药和其组合物。还提供了涉及这些新颖化合物或组合物的方法和试剂盒，用于治疗和/或预防增生性疾病（例如，癌症（例如，白血病、急性淋巴细胞白血病、淋巴瘤、伯基特淋巴瘤、黑色素瘤、多发性骨髓瘤、乳腺癌、尤因氏肉瘤、骨肉瘤、脑癌、卵巢癌、神经母细胞瘤、肺癌、结肠直肠癌）、良性肿瘤、与血管生成有关的疾病、炎症性疾病、自身炎症性疾病和自身免疫疾病）的主体。使用本发明的化合物或组合物治疗患有增生性疾病的主体可能抑制激酶（例如，细胞周期依赖性激酶（CDK）（例如，CDK12））的异常活性，从而诱导主体内的细胞凋亡和/或抑制转录。
• Efficient Synthesis of 3‐Mercaptoindoles via HI‐Promoted Sulfenylation of Indoles with Sodium Sulfinates
  作者：Shengnan Sun、Hexia Ye、Haibo Liu、Yongbiao Guo、Zhenhua Gao、Li Pan、Junchen Li、Xiaojing Bi

  DOI：10.1002/open.202300002

  日期：2023.3

  A new direct sulfenylation method of indoles by sodium sulfinates and hydroiodic acid was developed giving variety of 3-sulfenylindoles in high yields under mild conditions without using any catalysts or other additives. RS-I species generated in situ are supposed to be mainly responsible for the key electrophilic alkyl- or aryl-thiolation process.

  开发了一种用亚磺酸钠和氢碘酸直接磺基化吲哚的新方法，在不使用任何催化剂或其他添加剂的情况下，在温和条件下高产率地制备各种3-磺基吲哚。原位产生的 RS-I 物种被认为主要负责关键的亲电烷基或芳基硫醇化过程。
• Metal‐Free Regioselective Chlorosulfenylation of Indoles by Dimethylsulfoxide and 1,2‐Dichloroethane
  作者：Kuntal Palit、Niranjan Panda

  DOI：10.1002/ejoc.202400110

  日期：2024.4.22

  Csp2−H difunctionalization of indole was reported. The common solvents dimethyl sulfoxide (DMSO) and dichloroethane (DCE) were used as precursor to generate chlorodimethylsulfonium ion for electrophilic methylthiolation followed by chlorination by enabling 2-chloro-3-methylthioindoles.

  报道了一种简单且经济有效的无金属方法，用于吲哚的邻位 Csp2−H 双官能化。使用常用溶剂二甲亚砜（DMSO）和二氯乙烷（DCE）作为前体，生成氯二甲基锍离子，进行亲电甲硫基化，然后通过生成2-氯-3-甲硫基吲哚进行氯化。