2-mercapto-5,7-dimethylbenzoxazole | 89227-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-mercapto-5,7-dimethylbenzoxazole
• 英文别名: 5,7-dimethylbenzoxazole-2-thiol；5,7-dimethyl-2-mercaptobenzoxazole；2(3H)-Benzoxazolethione, 5,7-dimethyl-；5,7-dimethyl-3H-1,3-benzoxazole-2-thione
• CAS: 89227-88-3
• 化学式: C₉H₉NOS
• 分子量: 179.243
• InChiKey: HJZZWSFFYPMYOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-mercapto-5,7-dimethylbenzoxazole 在 sodium hydroxide 、 五氯化磷 、 一水合肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 苯 为溶剂， 反应 3.0h， 生成 3-[Amino-(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]propanenitrile
  参考文献：
  名称：

  3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives: inhibitors of immune complex induced inflammation

  摘要：

  3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives were evaluated in the dermal and pleural reverse passive Arthus reactions in the rat. In the pleural test these compounds were effective in reducing exudate volume and accumulation of white blood cells. This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin. The structural requirements for inhibiting the Arthus reactions were studied by systematic chemical modification of 1. These structure-activity relationship studies revealed that nitrogen 1' of the hydrazino group is essential for activity and must be electron rich, whereas chemical modifications of other sites of 1 had only a modest effect on activity.

  DOI：

  10.1021/jm00117a010
• 作为产物：
  描述：

  2,4-二甲基-6-硝基苯酚 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 2-mercapto-5,7-dimethylbenzoxazole
  参考文献：
  名称：

  Benzoxazole Derivatives as Novel 5-HT₃ Receptor Partial Agonists in the Gut

  摘要：

  A series of benzoxazoles with a nitrogen-containing heterocyclic substituent at the 2-position was prepared and evaluated for 5-HT3 partial agonist activity on isolated guinea pig ileum. The nature of the substituent at the 5-position of the benzoxazole ring affected the potency for the 5-HT3 receptor, and the 5-chloro derivatives showed increased potency and lowered intrinsic activity. 5-Chloro-7-methyl-2-(4-methyl-1-homopiperazinyl)benzoxazole (6v) exhibited a high binding affinity in the same range as that of the 5-HT3 antagonist granisetron, and its intrinsic activity was 12% of that of 5-HT. Compound 6v inhibited 5-HT-evoked diarrhea but did not prolong the transition time of glass beads in the normal distal colon even at a dose of 100 times the ED50 for diarrhea inhibition in mice. Compounds of this type are expected to be effective for the treatment of irritable bowel syndrome without the side effect of constipation.

  DOI：

  10.1021/jm9801004

文献信息

• Synthesis of new carbon-11 labeled benzoxazole derivatives for PET imaging of 5-HT3 receptor
  作者：Mingzhang Gao、Min Wang、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.ejmech.2007.10.017

  日期：2008.7

  in brain, heart and cancer diseases, and imaging agents for use in biomedical imaging technique PET. Benzoxazole derivatives are a novel class of 5-HT(3) receptor partial agonists with high binding affinity. Carbon-11 labeled benzoxazole derivatives have been synthesized as new potential PET radioligands for imaging 5-HT(3) receptor. The target tracers were prepared by N-[(11)C]methylation of their

  5-HT（3）受体是开发用于脑，心脏病和癌症疾病的治疗剂以及用于生物医学成像技术PET的成像剂的有吸引力的靶标。苯并恶唑衍生物是一类新型的具有高结合亲和力的5-HT（3）受体部分激动剂。碳11标记的苯并恶唑衍生物已被合成为用于成像5-HT（3）受体的新的潜在PET放射性配体。目标示踪剂是通过使用[（11）C] CH（3）OTf通过其相应前体的N-[（11）C]甲基化制备的，并通过HPLC纯化程序以40-50％的放射化学收率分离，将其衰减校正为基于[（11）C] CO（2）的轰炸（EOB）结束。从EOB开始，总的合成时间为20-25分钟。放射化学纯度> 99％，
• Serotonin 5-HT, receptor partial activator
  申请人：——

  公开号：US20010016579A1

  公开（公告）日：2001-08-23

  This invention provides a serotonin 5-HT 3 receptor partial activator which has a serotonin 5-HT 3 receptor activating action, in addition to its serotonin 5-HT 3 receptor antagonism, and does not cause constipation as a side effect. Particularly, based on the finding that newly synthesized benzoxazole derivatives typified by the compounds of the following formula (2) have strong serotonin 5-HT 3 receptor antagonism and serotonin 5-HT 3 receptor activating action, this invention provides these benzoxazole derivatives as serotonin 5-HT 3 receptor partial activators. 1 In the above formula, R 1 to R 4 may be the same or different from one another and each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted lower alkenyl group or a substituted or unsubstituted amino group, or two groups of R 1 and R 2 may be linked together to form a ring structure, namely benzene ring; R 5 represents a hydrogen atom, a substituted or unsubstituted lower alkyl group or a substituted or unsubstituted lower alkenyl group; and m is an integer of 1 to 4.

  本发明提供了一种5-HT3受体部分激动剂，该激动剂具有5-HT3受体激活作用，除了其5-HT3受体拮抗作用外，不会引起便秘等副作用。特别是，基于新合成的苯并咪唑衍生物发现，该衍生物以以下式子（2）的化合物为代表具有强烈的5-HT3受体拮抗作用和5-HT3受体激活作用，本发明提供这些苯并咪唑衍生物作为5-HT3受体部分激动剂。在上述公式中，R1到R4可以相同也可以不同，每个表示氢原子、卤素原子、取代或未取代的低级烷基、取代或未取代的低级烯基或取代或未取代的氨基；或R1和R2的两个基团可以连接在一起形成环结构，即苯环；R5表示氢原子、取代或未取代的低级烷基或取代或未取代的低级烯基；m是1到4的整数。
• Serotonin 5-HT3 receptor partial activator
  申请人：MEIJI SEIKA KAISHA, LTD.

  公开号：US20030013730A1

  公开（公告）日：2003-01-16

  This invention provides a serotonin 5-HT 3 receptor partial activator which has a serotonin 5-HT 3 receptor activating action, in addition to its serotonin 5-HT 3 receptor antagonism, and does not cause constipation as a side effect. Particularly, based on the finding that newly synthesized benzoxazole derivatives typified by the compounds of the following formula (2) have strong serotonin 5-HT 3 receptor antagonism and serotonin 5-HT 3 receptor activating action, this invention provides these benzoxazole derivatives as serotonin 5-HT 3 receptor partial activators. 1 In the above formula, R 1 to R 4 may be the same or different from one another and each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted lower alkenyl group or a substituted or unsubstituted amino group, or two groups of R 1 and R 2 may be linked together to form a ring structure, namely benzene ring; R 5 represents a hydrogen atom, a substituted or unsubstituted lower alkyl group or a substituted or unsubstituted lower alkenyl group; and m is an integer of 1 to 4.

  该发明提供了一种5-HT3受体部分激动剂，具有5-HT3受体激活作用，除了5-HT3受体拮抗作用外，不会引起便秘等副作用。特别地，基于新合成的苯并噁唑衍生物的发现，该衍生物以以下公式（2）的化合物为代表，具有强烈的5-HT3受体拮抗作用和5-HT3受体激活作用，该发明提供这些苯并噁唑衍生物作为5-HT3受体部分激动剂。在上述公式中，R1至R4可以相同或不同，每个代表氢原子、卤素原子、取代或未取代的低级烷基、取代或未取代的低级烯基或取代或未取代的氨基，或R1和R2的两个基团可以连接在一起形成环结构，即苯环；R5代表氢原子、取代或未取代的低级烷基或取代或未取代的低级烯基；m是1到4的整数。
• Serotonin 5-HT3, receptor partial activator
  申请人：Meiji Seika Kaisha Ltd.

  公开号：US06297246B1

  公开（公告）日：2001-10-02

  This invention provides a serotonin 5-HT3 receptor partial activator which has a serotonin 5-HT3 receptor activating action, in addition to its serotonin 5-HT3 receptor antagonism, and does not cause constipation as a side effect. Particularly, based on the finding that newly synthesized benzoxazole derivatives typified by the compounds of the following formula (2) have strong serotonin 5-HT3 receptor antagonism and serotonin 5-HT3 receptor activating action, this invention provides these benzoxazole derivatives as serotonin 5-HT3 receptor partial activators. In the above formula, R1 to R4 may be the same or different from one another and each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted lower alkenyl group or a substituted or unsubstituted amino group, or two groups of R1 and R2 may be linked together to form a ring structure, namely benzene ring; R5 represents a hydrogen atom, a substituted or unsubstituted lower alkyl group or a substituted or unsubstituted lower alkenyl group; and m is an integer of 1 to 4.

  本发明提供了一种5-HT3受体部分激动剂，其具有5-HT3受体激活作用，除了其5-HT3受体拮抗作用外，并不会引起便秘等副作用。特别地，基于新合成的苯并噁唑衍生物的发现，这些苯并噁唑衍生物具有强烈的5-HT3受体拮抗作用和5-HT3受体激活作用，本发明提供这些苯并噁唑衍生物作为5-HT3受体部分激动剂。在上述公式中，R1至R4可以相同或不同，每个代表氢原子、卤素原子、取代或未取代的低碳基、取代或未取代的低烯基或取代或未取代的氨基，或者R1和R2的两个基团可以连接在一起形成一个环结构，即苯环；R5代表氢原子、取代或未取代的低碳基或取代或未取代的低烯基；m为1到4的整数。
• Benzoxazole derivatives as serotonin 5-HT3 receptor partial activator
  申请人：MEIJI SEIKA KAISHA LTD.

  公开号：EP0806419A1

  公开（公告）日：1997-11-12

  This invention provides a serotonin 5-HT3 receptor partial activator which has a serotonin 5-HT3 receptor activating action, in addition to its serotonin 5-HT3 receptor antagonism, and does not cause constipation as a side effect. Particularly, based on the finding that newly synthesized benzoxazole derivatives typified by the compounds of the following formula (2) have strong serotonin 5-HT3 receptor antagonism and serotonin 5-HT3 receptor activating action, this invention provides these benzoxazole derivatives as serotonin 5-HT3 receptor partial activators. In the above formula, R1 to R4 may be the same or different from one another and each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted lower alkenyl group or a substituted or unsubstituted amino group, or two groups of R1 and R2 may be linked together to form a ring structure, namely benzene ring; R5 represents a hydrogen atom, a substituted or unsubstituted lower alkyl group or a substituted or unsubstituted lower alkenyl group; and m is an integer of 1 to 4.

  本发明提供了一种5-羟色胺5-HT3受体部分激活剂，它除了具有5-羟色胺5-HT3受体拮抗作用外，还具有5-羟色胺5-HT3受体激活作用，并且不会引起便秘副作用。 特别是，基于新合成的以下式（2）化合物为典型代表的苯并恶唑衍生物具有很强的血清素 5-HT3 受体拮抗作用和血清素 5-HT3 受体激活作用，本发明提供了这些苯并恶唑衍生物作为血清素 5-HT3 受体部分激活剂。 上式中，R1～R4可以相同或互不相同，各自代表氢原子、卤素原子、取代或未取代的低级烷基、取代或未取代的低级烯基或取代或未取代的氨基，也可以将R1和R2的两个基团连接在一起形成环状结构，即苯环；R5代表氢原子、取代或未取代的低级烷基或取代或未取代的低级烯基；m为1～4的整数。