6-methylthiokynurenic acid | 123158-10-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-methylthiokynurenic acid
• 英文别名: 6-methylthio-4-hydroxy-2-carboxyquinoline；6-Methylthio-4-oxo-1,4-dihydroquinoline-2-carboxylic acid；6-methylsulfanyl-4-oxo-1H-quinoline-2-carboxylic acid
• CAS: 123158-10-1
• 化学式: C₁₁H₉NO₃S
• 分子量: 235.263
• InChiKey: OOOBICRIERYUDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氨基茴香硫醚 在 sodium hydroxide 作用下， 生成 6-methylthiokynurenic acid
  参考文献：
  名称：

  Kynurenic acid derivatives useful in the treatment of neurodegenerative

  摘要：

  具有2-酸性基团或可在体内转化为该基团的4-氧代-1,4-二氢喹啉化合物及其药用可接受的盐是N-甲基-D-天冬氨酸（NMDA）受体的有效特异性拮抗剂，因此在治疗神经退行性疾病方面具有用途。具有2-酸性基团或可在体内转化为该基团的4-氧代-1,4-二氢喹啉化合物，除了羧基或C.sub.1-6烷氧羰基之外，是新颖的化合物，公式II的化合物也是新颖的，其中R.sup.2代表羧基或可在体内转化为该基团的基团，R.sup.6为氢，R.sup.5和R.sup.7代表C.sub.1-6烷基或卤素，但要求R.sup.5和R.sup.7不能同时是氯或溴；描述了制备这些新颖化合物的方法，以及含有这些新颖化合物的药物组合物。

  公开号：

  US05270309A1

文献信息

• [EN] 2-AMINOCARBONYL-QUINOLINE COMPOUNDS AS PLATELET ADENOSINE DIPHOSPHATE RECEPTOR ANTAGONISTS<br/>[FR] COMPOSES DE 2-AMINOCARBONYL-QUINOLINE UTILISES EN TANT QU'ANTAGONISTES DU RECEPTEUR DE L'ADENOSINE DIPHOSPHATE DES PLAQUETTES
  申请人：SCHERING AG

  公开号：WO2004052366A1

  公开（公告）日：2004-06-24

  Compounds of formula (I), where m, n, R1, R2, R3, R4 and R6 are described herein, are useful as inhibitors of platelet adenosine diphosphate. Pharmaceutical compositions containing these compounds, methods of using these compounds as antithrombotic agents and processes for synthesizing these compounds are also described herein.

  式（I）中的化合物，其中m、n、R1、R2、R3、R4和R6如本文所述，可用作血小板腺苷二磷酸酶抑制剂。本文还描述了含有这些化合物的药物组合物、使用这些化合物作为抗血栓剂的方法以及合成这些化合物的方法。
• Platelet adenosine diphosphate receptor antagonists
  申请人：Schering Aktiengesellschaft

  公开号：US20030060474A1

  公开（公告）日：2003-03-27

  Compounds of the following formula (I): 1 where a, b, R 1 , R 2 , R 4 and R 6 are described herein, are useful as inhibitors of platelet adenosine diphosphate. Pharmaceutical compositions containing these compounds, methods of using these compounds as antithrombotic agents and processes for synthesizing these compounds are also described herein.

  以下公式（I）的化合物：其中a、b、R1、R2、R4和R6如下所述，可用作抑制血小板腺苷二磷酸的药物。本文还描述了含有这些化合物的药物组合物，使用这些化合物作为抗血栓药物的方法以及合成这些化合物的过程。
• Direct Fluorescence Evaluation of <scp>d</scp>-Amino Acid Oxidase Activity Using a Synthetic <scp>d</scp>-Kynurenine Derivative
  作者：Tatsuya Sakamoto、Keiko Odera、Mayu Onozato、Hiroshi Sugasawa、Ryoya Takahashi、Yasuto Fujimaki、Takeshi Fukushima

  DOI：10.1021/acs.analchem.2c00775

  日期：2022.10.25

  d-Amino acid oxidase (DAO) has been suggested to be associated with the central nervous system diseases, such as schizophrenia. We newly synthesized a nonfluorescent 5-methylthio-d-kynurenine (MeS-d-KYN), which was converted to blue-fluorescent 6-MeS-kynurenic acid (MeS-KYNA, λex = 364 nm, λem = 450 nm) through a one-step reaction by incubation with DAO. It was revealed that fluorescence intensity increased accompanied by commercial porcine kidney DAO activity (unit) with a good correlation (R2 = 0.9972), suggesting that the fluorometric evaluation of DAO activity using MeS-d-KYN is feasible. MeS-d-KYN was applied to fluorescent DAO imaging in cultured LLC-PK1 cells, and the blue fluorescence of MeS-KYNA overlapped considerably with the location of peroxisomes, which was suggested to be the location of DAO in the cells. Because fluorescence was diminished in the presence of 6-chloro-1,2-benzisoxazol-3(2H)-one (CBIO), a DAO inhibitor, it was considered that DAO activity in cells could be directly evaluated using MeS-d-KYN as the substrate.

  d-氨基氧化酶（DAO）被认为与精神分裂症等中枢神经系统疾病有关。我们新合成了非荧光5-甲基硫代-d-喹啉（MeS-d-KYN），通过与DAO孵育一步反应，将其转化为蓝色荧光6-甲基硫代-喹啉酸（MeS-KYNA，λex = 364 nm，λem = 450 nm）。结果表明，荧光强度随商业猪肾DAO活性（单位）的增加而增加，相关性良好（R2 = 0.9972），表明使用MeS-d-KYN对DAO活性进行荧光测定是可行的。MeS-d-KYN被用于培养的LLC-PK1细胞中DAO的荧光成像，MeS-KYNA的蓝色荧光与过氧化物酶体的位置高度重叠，这表明过氧化物酶体是细胞中DAO的所在地。由于在DAO抑制剂6-氯-1,2-苯并异恶唑-3(2H)-酮（CBIO）存在下荧光减弱，因此认为可以使用MeS-d-KYN作为底物直接评估细胞中的DAO活性。
• Kynurenic acid derivatives useful in the treatment of neurodegenerative disorders
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0303387A1

  公开（公告）日：1989-02-15

  4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, and their pharmaceutically acceptable salts, are potent specific antagonists of N-methyl-D-­aspartate (NMDA) receptors and are therefore useful in the treatment of neurodegenerative disorders. 4-Oxo-1,4-dihydroquinoline compounds having a 2-­acidic group or a group convertible thereto in vivo, other than carboxy or C₁₋₆ alkoxycarbonyl, are novel compounds, as also are compounds of formula II wherein R² represents carboxy or a group convertible thereto in vivo, R⁶ is hydrogen and R⁵ and R⁷ represent C₁₋₆ alkyl or halogen, provided that R⁵ and R⁷ are not simultaneously chlorine or simultaneously bromine; a process for preparing the novel compounds is described, as also are pharmaceutical compositions containing the novel compounds.

  具有 2-酸性基团或体内可转化基团的 4-氧代-1,4-二氢喹啉化合物及其药学上可接受的盐类是 N-甲基-D-天冬氨酸（NMDA）受体的强效特异性拮抗剂，因此可用于治疗神经退行性疾病。除羧基或 C₁₋₆ 烷氧羰基外，具有 2-酸性基团或在体内可转化的基团的 4-氧代-1,4-二氢喹啉化合物是新型化合物，如式 II 所示的化合物 其中 R² 代表羧基或体内可转化为羧基的基团，R⁶ 是氢，R⁵ 和 R⁷ 代表 C₁₋₆ 烷基或卤素，但 R⁵ 和 R⁷ 不能同时为氯或同时为溴。
• 2-AMINOCARBONYL-QUINOLINE COMPOUNDS AS PLATELET ADENOSINE DIPHOSPHATE RECEPTOR ANTAGONISTS
  申请人：Schering Aktiengesellschaft

  公开号：EP1578423A1

  公开（公告）日：2005-09-28