5-ethoxycarbonyl-2-mercaptobenzoxazole | 162959-44-6

• 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: 5-ethoxycarbonyl-2-mercaptobenzoxazole
• 英文别名: ethyl 2-sulfanylidene-3H-1,3-benzoxazole-5-carboxylate
• CAS: 162959-44-6
• 化学式: C₁₀H₉NO₃S
• 分子量: 223.252
• InChiKey: QQZZZWFZFUQPBS-UHFFFAOYSA-N

物化性质

• 沸点：
  342.5±44.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-ethoxycarbonyl-2-mercaptobenzoxazole 在 五氯化磷 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 Ethyl 2-[[2-(4-fluorophenyl)-1-pyridin-2-ylethyl]amino]-1,3-benzoxazole-5-carboxylate
  参考文献：
  名称：

  苯并恶唑胺和苯并噻唑胺：白三烯生物合成的有效，对映选择性抑制剂，具有新颖的作用机理。

  摘要：

  描述了一系列抑制白三烯（LT）生物合成的苯并恶唑胺和苯并噻唑胺类似物。最初的铅（S）-N-（苯并噻唑-2-基）苯丙氨酸乙酯（5a）在筛选程序中被发现，该程序可抑制Ca-离子载体-A23187诱导的人多形核白细胞释放LTB4（IC50 0.23 microM ）。通过结构修饰，确定了5-位上的疏水取代基以及苯丙氨酸的苯环被环己基取代极大地增强了效能。描述了几种保留效力和对映异构体选择性的酯类生物甾体。铅优化最终达到（S）-N- [2-环己基-1-（2-吡啶基）乙基] -5-甲基-2-苯并恶唑胺+ ++（43b），IC50 0.001 microM。所述化合物不是5-脂氧合酶的抑制剂，而是

  DOI：

  10.1021/jm00033a008
• 作为产物：
  描述：

  4-羟基-3-硝基苯甲酸乙酯 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 乙醇 为溶剂， 生成 5-ethoxycarbonyl-2-mercaptobenzoxazole
  参考文献：
  名称：

  Regulatory molecules for the 5-HT3 receptor ion channel gating system

  摘要：

  Substituted benzoxazole derivatives which possess a nitrogen containing heterocycle at C2 are selective partial agonists of the 5-HT3 receptor. Alteration of substituents on the benzoxazole nucleus affords both agonist-like and antagonist-like compounds, and uniquely modifies the function of the 5-HT3 receptor ion channel gating system. SAR and corroborative computational docking study for these partial agonists successfully explained structure and function of the 5-HT3 receptor. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.054

文献信息

• Amide compounds and use of the same
  申请人：Japan Tobacco Inc.

  公开号：US06174887B1

  公开（公告）日：2001-01-16

  An amide compound of the formula (I): wherein R is amino and the like, A is alkylene and the like, X is O, S and the like, M is arylene and the like, R1, R2, R3 and R4 are H, hydroxy and the like, R5 is H, alkyl and the like, m is an integer of 0-6, R6 is an optionally substituted aryl and the like, and R7 is H, an optionally substituted alkyl and the like, a pharmaceutically acceptable acid addition salt thereof and a pharmaceutical containing same as an active ingredient. The amide compounds exhibit superior suppressive effects on cytokines directly or indirectly involved in inflammations, such as IL-8, IL-1, IL-6, TNF-&agr;, GM-CSF and the like, and are useful for the prophylaxis and treatment of rheumatic diseases, arthritis due to gout and the like.

  化合物的结构式（I）如下： 其中R为氨基等，A为烷基等，X为O、S等，M为芳基等，R1、R2、R3和R4为H、羟基等，R5为H、烷基等，m为0-6的整数，R6为可选择取代的芳基等，R7为H、可选择取代的烷基等，其药学上可接受的酸盐和含有其作为活性成分的药物。这些酰胺化合物对直接或间接参与炎症的细胞因子，如IL-8、IL-1、IL-6、TNF-α、GM-CSF等，表现出优越的抑制作用，并可用于预防和治疗风湿病、痛风性关节炎等。
• Amide compounds and use thereof
  申请人：Japan Tobacco Inc.

  公开号：US06420561B1

  公开（公告）日：2002-07-16

  An amide compound of the formula (I): wherein R is amino and the like, A is alkylene and the like, X is O, S and the like, M is arylene and the like, R1, R2, R3 and R4 are H, hydroxy and the like, R5 is H, alkyl and the like, m is an integer of 0-6, R6 is an optionally substituted aryl and the like, and R7 is H, an optionally substituted alkyl and the like, a pharmaceutically acceptable acid addition salt thereof and a pharmaceutical containing same as an active ingredient. The amide compounds exhibit superior suppressive effects on cytokines directly or indirectly involved in inflammations, such as IL-8, IL-1, IL-6, TNF-&agr;, GM-CSF and the like, and are useful for the prophylaxis and treatment of rheumatic diseases, arthritis due to gout and the like.

  式(I)的酰胺化合物：其中R为氨基或类似物，A为亚烷基或类似物，X为O、S或类似物，M为芳烃基或类似物，R1、R2、R3和R4为H、羟基或类似物，R5为H、烷基或类似物，m为0-6的整数，R6为可选取代的芳基或类似物，R7为H、可选取代的烷基或类似物，其药学上可接受的酸盐和含有其作为活性成分的药物。这些酰胺化合物表现出优越的抑制作用，直接或间接地涉及炎症的细胞因子，如IL-8、IL-1、IL-6、TNF-α、GM-CSF等，可用于预防和治疗风湿性疾病、痛风性关节炎等。
• Electrochemical Desulfurizative Amination of Heteroaromatic Thiols by Iodine Catalysis
  作者：Tingting Ran、Wei Jiang、Xin Fu、Jinguo Long、Jie Liu

  DOI：10.1002/cctc.202301750

  日期：——

  We report that anodic oxidation of 2-iodobenzoic acid enables a hypervalent iodine (III) electrocatalysis of desulfurizative amination of heteroaromatic thiols. This protocol features broad substrate scope and wide functional group tolerance, delivering the target N-heterocyclic amines with good to excellent yields.

  我们报道，2-碘苯甲酸的阳极氧化能够实现杂芳族硫醇脱硫胺化的高价碘（III）电催化。该方案具有广泛的底物范围和广泛的官能团耐受性，以良好至优异的产率提供目标N -杂环胺。
• Carboxylic acid compound and use thereof
  申请人：Japan Tobacco Inc.

  公开号：EP1304322A2

  公开（公告）日：2003-04-23

  A carboxylic acid compound of the formula (I-a) wherein R is amino and the like, A is alkylene and the like, X is O, S and the like, M is arylene and the like, R1, R2, R3 and R4 are H, hydroxy and the like. The carboxylic acid compound of the formula (I-a) can be used for making an amide compound of the formula (I): wherein R, A, X, R1, R2, R3 and R4 are as described above and R5 is H, alkyl and the like, m is an integer of 0-6, R6 is an optionally substituted aryl and the like, and R7 is H, an optionally substituted alkyl and the like, a pharmaceutically acceptable acid addition salt thereof and a pharmaceutical containing same as an active ingredient. The amide compounds exhibit superior suppressive effects on cytokines directly or indirectly involved in inflammations, such as IL-8, IL-1, IL-6, TNF-α, GM-CSF and the like, and are useful for the prophylaxis and treatment of rheumatic diseases, arthritis due to gout and the like.

  式（I-a）的羧酸化合物 其中 R 是氨基等，A 是亚烷基等，X 是 O、S 等，M 是芳基等，R1、R2、R3 和 R4 是 H、羟基等。 式（I-a）的羧酸化合物可用于制造式（I）的酰胺化合物： 其中 R、A、X、R1、R2、R3 和 R4 如上所述，R5 为 H、烷基等，m 为 0-6 的整数，R6 为任选取代的芳基等，R7 为 H、任选取代的烷基等。这些酰胺化合物对直接或间接参与炎症的细胞因子，如 IL-8、IL-1、IL-6、TNF-α、GM-CSF 等具有卓越的抑制作用，可用于预防和治疗风湿性疾病、痛风引起的关节炎等。
• 3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives: inhibitors of immune complex induced inflammation
  作者：Fortuna Haviv、James D. Ratajczyk、Robert W. DeNet、Francis A. Kerdesky、Roland L. Walters、Steven P. Schmidt、James H. Holms、Patrick R. Young、George W. Carter

  DOI：10.1021/jm00117a010

  日期：1988.9

  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.