2-氰基-6-甲氧基苯并噻唑 | 129058-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-氰基-6-甲氧基苯并噻唑
• 英文名称: 6-hydroxybenzo[d]thiazole-2-carboxylic acid
• 英文别名: 6-hydroxybenzothiazole-2-carboxylic acid；6-Hydroxy-1,3-benzothiazole-2-carboxylic acid
• CAS: 129058-50-0
• 化学式: C₈H₅NO₃S
• 分子量: 195.199
• InChiKey: XHWLNNUYRRZHSM-UHFFFAOYSA-N

物化性质

• 熔点：
  128-132 °C(Solv: water (7732-18-5))
• 沸点：
  465.3±37.0 °C(Predicted)
• 密度：
  1.665±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氰基-6-甲氧基苯并噻唑 在 sodium hydroxide 作用下， 以0.7 g的产率得到6-羟基苯并噻唑
  参考文献：
  名称：

  由1,4-苯醌合成脱氢荧光素[2-（6'-羟基-2'-苯并噻唑基）-噻唑-4-羧酸]的新方法

  摘要：

  萤光素的氧化产物脱氢萤光素[2-（6'-羟基-2'-苯并噻唑基）-噻唑-4-羧酸]的新合成是从1,4-苯醌开始的。该化合物与1-半胱氨酸乙酯反应，然后进行氧化-环化步骤，得到2-羧乙氧基-6-羟基苯并噻唑，将其原位水解并脱羧成6-羟基苯并噻唑。对该关键中间体的叔丁基（二甲基）甲硅烷基醚进行α-锂化，然后用DMF进行甲酰化，并将所得醛与1-半胱氨酸乙酯缩合。中间体噻唑烷脱氢，然后脱保护，得到脱氢萤光素，其从1,4-苯醌的总产率为35％（从6-羟基苯并噻唑的产率为69％）。

  DOI：

  10.1016/j.tet.2013.05.019
• 作为产物：
  描述：

  Methyl 2-methoxy-7-hydroxy-2H-benzo[1,4]thiazine-3-carboxylate 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 24.25h， 生成 2-氰基-6-甲氧基苯并噻唑
  参考文献：
  名称：

  Loewik, Dennis W. P. M.; Tisi, Lawrence C.; Murray, James A. H., Synthesis, 2001, # 12, p. 1780 - 1783

  摘要：

  DOI：

文献信息

• A fluorescent probe for rapid aqueous fluoride detection and cell imaging
  作者：Bowen Ke、Weixuan Chen、Nanting Ni、Yunfeng Cheng、Chaofeng Dai、Hieu Dinh、Binghe Wang

  DOI：10.1039/c2cc37270c

  日期：——

  A stable and highly selective fluorescent probe has been designed and synthesized for the rapid detection of fluoride ions (F−) in aqueous solution and living cells. The design was based on the high reactivity of F− toward a silyl group.

  一种稳定且高选择性的荧光探针已被设计和合成，用于在水溶液和活细胞中快速检测氟离子（F−）。设计基于F−对硅基团的高反应性。
• Selective NR1/2B <i>N</i>-Methyl-<scp>d</scp>-aspartate Receptor Antagonists among Indole-2-carboxamides and Benzimidazole-2-carboxamides
  作者：István Borza、Éva Bozó、Gizella Barta-Szalai、Csilla Kiss、Gábor Tárkányi、Ádám Demeter、Tamás Gáti、Viktor Háda、Sándor Kolok、Anikó Gere、László Fodor、József Nagy、Kornél Galgóczy、Ildikó Magdó、Béla Ágai、József Fetter、Ferenc Bertha、György M. Keserü、Csilla Horváth、Sándor Farkas、István Greiner、György Domány

  DOI：10.1021/jm060420k

  日期：2007.3.1

  (4-Benzylpiperidine-1-yl)-(6-hydroxy-1H-indole-2-yl)-methanone (6a) derived from (E)-1-(4-benzylpiperidin-1-yl)-3-(4-hydroxy-phenyl)-propenone (5) was identified as a potent NR2B subunit-selective antagonist of the NMDA receptor. To establish the structure-activity relationship (SAR) and to attempt the improvement of the ADME properties of the lead, a series of compounds were prepared and tested. Several derivatives showed low nanomolar activity both in the binding and in the functional assay. In a formalin-induced hyperalgesia model in mice, 6a and (4-benzylpiperidine-1-yl)-[5(6)-hydroxy-1H-benzimidazol-2-yl]-methanone (60a) were as active as besonprodil (2) after oral administration. A CoMSIA model was developed based on binding data of a series of indole- and benzimidazole-2-carboxamides.

  (4-苄基哌啶-1-基)-(6-羟基-1H-吲哚-2-基)-甲酮(6a)是从(E)-1-(4-苄基哌啶-1-基)-3-(4-羟基苯基)丙烯酮(5)中鉴定出的一种强效的NMDA受体NR2B亚基选择性拮抗剂。为了建立结构-活性关系(SAR)并尝试改善先导化合物的ADME性质，制备并测试了一系列化合物。多种衍生物在结合和功能性测定中均显示出低纳摩尔的活性。在环磷酰胺诱导的小鼠痛觉过敏模型中，6a和(4-苄基哌啶-1-基)-[5(6)-羟基-1H-联吡啶-2-基]-甲酮(60a)在口服给药后与Besonprodil(2)具有相同的活性。基于一系列吲哚-和联吡啶-2-羧酰胺的结合数据，开发了一种CoMSIA模型。
• Quaternary Ammonium Promoted Ultra Selective and Sensitive Fluorescence Detection of Fluoride Ion in Water and Living Cells
  作者：Long Li、Yuzhuo Ji、Xinjing Tang

  DOI：10.1021/ac503177n

  日期：2014.10.21

  Highly selective and sensitive fluorescent probes with a quaternary ammonium moiety have been rationally designed and developed for fast and sensitive fluorescence detection of fluoride ion (F– from NaF, not TBAF) in aqueous solution and living cells. With the sequestration effect of quaternary ammonium, the detection time was less than 2 min and the detection limit of fluoride ion was as low as 0

  合理设计和开发了具有季铵部分的高选择性和灵敏的荧光探针，用于快速，灵敏的荧光检测水溶液和活细胞中的氟离子（来自NaF的F –而不是TBAF）。由于具有季铵盐的螯合作用，检测时间少于2分钟，氟离子的检出限低至0.57 ppm，这是文献中许多氟化物荧光探针在水溶液中的最低检出限。
• [EN] AMIDE DERIVATIVES AS NMDA RECEPTOR ANTAGONISTS<br/>[FR] DERIVES AMIDIQUES COMME ANTAGONISTES DU RECEPTEUR NMDA
  申请人：RICHTER GEDEON VEGYESZET

  公开号：WO2002034718A1

  公开（公告）日：2002-05-02

  The invention relates to new NR2B selective NMDA receptor antagonist carboxylic acid amide derivatives of formula (I) as well as the recemates, optical antipodes and the salts thereof formed with acids and bases. Fruthermore objets of the present invention are the pharmaceutical compositions containing compounds of formula (I) or the salts thereof as active ingredients, as well as the synthesis of compounds of formula (I), and the chemical and pharmaceutical manufacture of medicaments containing these compounds, as well as the method of treatments with these compounds, which means administering to a mammal to be treated - including human - effective amount/amounts of compounds of formula (I) of the present invention as such or as medicament. The new carboxylic acid amide derivatives of formula (I) of the present invention are highly effective and selective antagonists of NMDA receptor, and moreover most of the compounds are selective antagonist of NR2B subtype of NMDA receptor.

  本发明涉及公式（I）的新型NR2B选择性NMDA受体拮抗剂羧酸酰胺衍生物，以及与酸和碱形成的外消旋体，光学对映体和其盐。此外，本发明的目标是含有公式（I）化合物或其盐作为活性成分的制药组合物，以及公式（I）化合物的合成，以及含有这些化合物的药物的化学和制药制造，以及使用这些化合物的治疗方法，即向待治疗的哺乳动物（包括人类）施用本发明的化合物的有效量/量，作为药物或单独使用。本发明的新型羧酸酰胺衍生物的公式（I）是高效和选择性的NMDA受体拮抗剂，而且大多数化合物是NMDA受体NR2B亚型的选择性拮抗剂。
• Carboxamide Compounds and Methods for Using The Same
  申请人：Yu Jiaxin

  公开号：US20090275609A1

  公开（公告）日：2009-11-05

  Disclosed are carboxamide compounds, as well as pharmaceutical compositions and methods of use. One embodiment is a compound having the structure in which R 1 , R 2 , R 3 , R 4 , D, J, Z, T, p, q, w and x are as described herein. In certain embodiments, a compound disclosed herein activates the AMPK pathway, and can be used to treat metabolism-related disorders and conditions.

  本发明涉及羧酰胺化合物、以及制备该化合物的药物组合物和使用方法。其中一种实施例是具有以下结构的化合物，其中R1、R2、R3、R4、D、J、Z、T、p、q、w和x如本文所述。在某些实施例中，本文所述的化合物可激活AMPK途径，并可用于治疗代谢相关的疾病和状况。