2-硫氧代-1,2-二氢吡啶-3-羧酸甲酯 | 74470-32-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-硫氧代-1,2-二氢吡啶-3-羧酸甲酯
• 英文名称: methyl 2-mercaptonicotinate
• 英文别名: 2-mercaptonicotinic acid methylester；3-methoxycarbonyl-2-mercaptopyridine；methyl 2-sulfanylidene-1H-pyridine-3-carboxylate
• CAS: 74470-32-9
• 化学式: C₇H₇NO₂S
• 分子量: 169.204
• InChiKey: BQQXUGGTSVMBLL-UHFFFAOYSA-N

物化性质

• 熔点：
  204 °C
• 沸点：
  265.8±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  70.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-硫氧代-1,2-二氢吡啶-3-羧酸甲酯 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 生成 2-硫代-1,2-二氢-3-吡啶甲酰肼
  参考文献：
  名称：

  Triazolothiadizepinylquinolines as potential MetAP-2 and NMT inhibitors: Microwave-assisted synthesis, pharmacological evaluation and molecular docking studies

  摘要：

  The enzymes MetAP-2 and NMT play a crucial role in the process of myristoylation of oncoproteins which is deregulated in many types of cancers. Execution of both these enzymes is considered as strategy for the intervention of various cancers and relative fungal infections, and hence the discovery of novel MetAP-2 and NMT inhibitors necessitate their high relevancy. In this investigation, we have synthesized a series of novel seven-membered triazolothiadiazepinyl quinolines 10(a-m) distinctively under microwave irradiation technique and identified as selective MetAP-2 and NMT inhibitors. Amongst the functionalized derivatives when evaluated for the in vitro antifungal assay, compounds 10b, 10c, 10e and 10f were considered promising due to notable inhibitory effects (MIC = 0.2 mg/mL) on Aspergillus fumigatus. Screening of the anticancer activity against NCI-60 Human tumor cell lines portrayed that conjugates 10b, 10c, 10e and 10f were found to be moderately effective against the Renal Cancer cell line UO-31. The data acquired from biological studies was further validated by molecular docking studies and p harmaco kinetic evaluation. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.127445
• 作为产物：
  描述：

  2-羟基烟酸 在 sodium hydrogensulfide 、 乙醇 、 五氯化磷 、 硫酸 、 三氯氧磷 作用下， 生成 2-硫氧代-1,2-二氢吡啶-3-羧酸甲酯
  参考文献：
  名称：

  水杨酸酯的吡啶和吡嗪类似物的合成和研究。

  摘要：

  DOI：

  10.1021/ja01191a113

文献信息

• [EN] PEPTIDE MACROCYCLES AGAINST ACINETOBACTER BAUMANNII<br/>[FR] MACROCYCLES PEPTIDIQUES CONTRE ACINETOBACTER BAUMANNII
  申请人：HOFFMANN LA ROCHE

  公开号：WO2017072062A1

  公开（公告）日：2017-05-04

  The present invention provides compounds of formula (I) wherein X1 to X8 and R1 to R8 are as described herein, as well as pharmaceutically acceptable salts thereof. Further the present invention is concerned with the manufacture of the compounds of formula (I), pharmaceutical compositions comprising them and their use as medicaments for the treatment of diseases and infections caused by Acinetobacter baumannii.

  本发明提供了式（I）的化合物，其中X1至X8和R1至R8如本文所述，以及其药学上可接受的盐。此外，本发明涉及制备式（I）的化合物，包括它们的药物组合物以及它们作为治疗由鲍曼不动杆菌引起的疾病和感染的药物的用途。
• [EN] INDOLES AND THEIR THERAPEUTIC USE<br/>[FR] INDOLES ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：ARGENTA DISCOVERY LTD

  公开号：WO2009077728A1

  公开（公告）日：2009-06-25

  Compound of formula (I) are are ligands of the CRTH2 receptor, useful inter alia for treatment of inflammatory conditions. Wherein X is -SO2- or *-SO2NR3- wherein the bond marked with an asterisk is attached to Ar1; R1 is hydrogen, fluoro, chloro, CN or CF3; R2 is hydrogen, fluoro or chloro; R3 is hydrogen, C1C8alkyl or C3-C7cycloalkyl; Ar1 is phenyl or a 5- or 6-membered heteroaryl group selected from furanyl, thienyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl and pyrazinyl, wherein the phenyl or heteroaryl groups are optionally substituted by one or more substituents independently selected from fluoro, chloro, CN, C3- C7cycloalkyl, -O(C1-C4alkyl) or C1C6alkyl, the latter two groups being optionally substituted by one or more fluoro atoms; and Ar2 is phenyl or 5- or 6-membered heteroaryl group selected from pyrrolyl, furanyl, thienyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl and pyrazinyl, wherein the phenyl or heteroaryl groups are optionally substituted by one or more substituents independently selected from fluoro, chloro, CN, C3- C3- C7cycloalkyl, -O(C1-C4alkyl) or C1C6alkyl, the latter two groups being optionally substituted by one or more fluoro atoms.

  式(I)的化合物是CRTH2受体的配体，尤其适用于治疗炎症性疾病。其中，X为-SO2-或*-SO2NR3-，其中带有星号的键连接到Ar1；R1为氢、氟、氯、氰基或三氟甲基；R2为氢、氟或氯；R3为氢、C1-C8烷基或C3-C7环烷基；Ar1为苯基或选自呋喃基、噻吩基、噁唑基、噻唑基、咪唑基、吡唑基、异噁唑基、异噻唑基、吡啶基、吡嗪基、嘧啶基和哒嗪基的5或6元杂芳基，其中苯基或杂芳基可任选地被一个或多个独立选自氟、氯、氰基、C3-C7环烷基、-O(C1-C4烷基)或C1-C6烷基的取代基取代，后两个基团可任选地被一个或多个氟原子取代；Ar2为苯基或选自吡咯基、呋喃基、噻吩基、噁唑基、噻唑基、咪唑基、吡唑基、异噁唑基、异噻唑基、吡啶基、吡嗪基、嘧啶基和哒嗪基的5或6元杂芳基，其中苯基或杂芳基可任选地被一个或多个独立选自氟、氯、氰基、C3-C7环烷基、-O(C1-C4烷基)或C1-C6烷基的取代基取代，后两个基团可任选地被一个或多个氟原子取代。
• 一种含氮脂肪醇酯钡盐及其制备方法、组合物和应用
  申请人：浙江传化华洋化工有限公司

  公开号：CN110229097A

  公开（公告）日：2019-09-13

  本发明公开了一种含氮脂肪醇酯钡盐及其制备方法、组合物和应用。本发明提供一种含氮脂肪醇酯钡盐，其化学式为Ba(C7H3O2NSR)2，R为C12～20的烷基；该钡盐属于硫醇盐，兼具抗氧剂作用，能显著提高PVC的长效稳定性。本发明的钡盐含有氮原子，其与含氮锌盐及辅助稳定剂组合而成的稳定剂，能明显改善PVC的热稳定性能，且含氮锌的活性大于普通羧酸锌，能更快速吸收烯丙基氯，显著提高初期着色和延长后期锌烧。
• [EN] INDOLE DERIVATIVES AS LIGANDS OF CRTH2 RECEPTORS<br/>[FR] DÉRIVÉS D'INDOLE EN TANT QUE LIGANDS DES RÉCEPTEURS CRTH2
  申请人：PULMAGEN THERAPEUTICS ASTHMA LTD

  公开号：WO2010142934A1

  公开（公告）日：2010-12-16

  The following compounds are CRTH2 antagonists, useful in treatment of respiratory disease: 3-[3-chloro-4-(pyridine-2-sulfonyl)isothiazol-5-ylmethyl]-5-fluoro-2- methylindol-1-yl}acetic acid, [3-(5-benzenesulfonyl-3-methyl-3H-imidazol-4-ylmethyl)-5-fluoro-2- methylindol-1-yl]acetic acid, [3-(5-benzenesulfonyloxazol-4-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid, [3-(3-benzenesulfonyl-4-met ylthiophen-2-ylmethyl)-5-fluoro-2-methylindol-1- yl]acetic acid, 5-fluoro-2-methyl-3-[2-(pyridin-2-ylsulfamoyl)benzyl]indol-1-yl}acetic acid, 5-fluoro-2-methyl-3-[4-methyl-3-(pyridine-2-sulfonyl)thiophen-2- ylmethyl]indol-1-yl}acetic acid, 5-fluoro-2-methyl-3-[3-methyl-5-(pyridine-2-sulfonyl)-3H-imidazol-4- ylmethyl]indol-1-yl}acetic acid, 5-fluoro-3-[2-(3-fluorophenylsulfamoyl)pyridin-3-ylmethyl]-2-methylindol-1- yl}acetic acid, [3-(4-benzenesulfonyloxazol-5-ylmethyl)-5-fluoro-2-methylindol-1- yl]acetic acid, 3-[2-(3-cyanophenylsulfamoyl)benzyl]-5-fluoro-2-methylindol-1-yl}acetic acid, [3-(4-benzenesulfonylthiazol-5-ylmethyl)-5-chloro-2-methyl-indol-1-yl]acetic acid, [3-(4-benzenesulfonyl-2-methylthiazol-5-ylmethyl)-5-fluoro-2-methylindol-1- yl]acetic acid, and [3-(4-benzenesulfonyl-3-methylisothiazol-5-ylmethyl)-5-fluoro-2- methylindol-1-yl]acetic acid.

  以下化合物是CRTH2拮抗剂，可用于治疗呼吸道疾病：3-[3-氯-4-(吡啶-2-磺酰基)异噻唑-5-基甲基]-5-氟-2-甲基吲哚-1-基}乙酸，[3-(5-苯磺酰基-3-甲基-3H-咪唑-4-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸，[3-(5-苯磺酰氧咪唑-4-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸，[3-(3-苯磺酰基-4-甲硫代吡啶-2-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸，5-氟-2-甲基-3-[2-(吡啶-2-基磺酰胺基)苯基]吲哚-1-基}乙酸，5-氟-2-甲基-3-[4-甲基-3-(吡啶-2-磺酰基)噻吩-2-基甲基]吲哚-1-基}乙酸，5-氟-2-甲基-3-[3-甲基-5-(吡啶-2-磺酰基)-3H-咪唑-4-基甲基]吲哚-1-基}乙酸，5-氟-3-[2-(3-氟苯基磺酰胺基)吡啶-3-基甲基]-2-甲基吲哚-1-基}乙酸，[3-(4-苯磺酰氧咪唑-5-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸，3-[2-(3-氰苯基磺酰胺基)苯基]-5-氟-2-甲基吲哚-1-基}乙酸，[3-(4-苯磺酰基噻唑-5-基甲基)-5-氯-2-甲基吲哚-1-基]乙酸，[3-(4-苯磺酰基-2-甲基噻唑-5-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸，和[3-(4-苯磺酰基-3-甲基异噻唑-5-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸。
• A Convenient Preparation of Heteroaryl Sulfonamides and Sulfonyl Fluorides from Heteroaryl Thiols
  作者：Stephen W. Wright、Kelly N. Hallstrom

  DOI：10.1021/jo052164+

  日期：2006.2.1

  thiols may be oxidized to the sulfonyl chloride at low temperature (−25 °C) by using 3.3 equiv of aqueous sodium hypochlorite. The reaction is rapid, avoids the use of chlorine gas, and succeeds with substrates that have previously been found to afford little or none of the sulfonamide product with other procedures. The method allows the preparation of the sulfonyl fluorides, which are stable enough to

  杂芳族硫醇可通过使用3.3当量的次氯酸钠水溶液在低温（−25°C）下氧化为磺酰氯。该反应是快速的，避免了使用氯气，并且成功地使用了以前发现的底物，该底物在其他方法下几乎没有或根本没有提供磺酰胺产物。该方法允许制备磺酰氟，该磺酰氟足够稳定以被纯化和储存，从而使其成为潜在的有用的单体，可用于平行化学研究中。