2-(3-methoxy-4-(oxazol-5-yl)phenylamino)-2-oxoacetic acid | 267406-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-methoxy-4-(oxazol-5-yl)phenylamino)-2-oxoacetic acid
• 英文别名: [[3-Methoxy-4-(5-oxazolyl)phenyl]amino]oxoacetic Acid；N-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamic acid；2-[3-methoxy-4-(1,3-oxazol-5-yl)anilino]-2-oxoacetic acid
• CAS: 267406-36-0
• 化学式: C₁₂H₁₀N₂O₅
• 分子量: 262.222
• InChiKey: YONOWKMQNCUMMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-methoxy-4-(oxazol-5-yl)phenylamino)-2-oxoacetic acid 在 N-甲基吗啉 、 三乙基硅烷 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  [EN] ANTICANCER AGENTS
  [FR] AGENTS ANTICANCÉREUX

  摘要：

  该发明提供了一种该发明的化合物，该化合物为A-X-L-B式的化合物或其盐，以及包含该发明的化合物的组合物，以及包括给予该发明的化合物的治疗方法。该发明的化合物可用作治疗剂，用于治疗癌症等疾病。

  公开号：

  WO2009018344A1
• 作为产物：
  描述：

  (2-甲氧基-4-硝基苯基)二乙酸甲二醇酯 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 2-(3-methoxy-4-(oxazol-5-yl)phenylamino)-2-oxoacetic acid
  参考文献：
  名称：

  Novel diamide-Based inhibitors of IMPDH

  摘要：

  A series of novel amide-based small molecule inhibitors of inosine monophosphate dehydrogenase is described. The synthesis and the structure-activity relationships (SARs) derived front in vitro studies are presented. (C). 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00132-4

文献信息

• Oxamide IMPDH inhibitors
  申请人：——

  公开号：US20020052513A1

  公开（公告）日：2002-05-02

  Disclosed are compounds of the general formula 1 which are oxamide derivatives and inhibitors of the enzyme inosine monophosphate dehydrogenase (IMPDH).

  揭示了一般式1的化合物，这些化合物是羟酰胺衍生物，是肌醇单磷酸脱氢酶（IMPDH）的抑制剂。
• Novel inhibitors of IMPDH enzyme
  申请人：——

  公开号：US20040082562A1

  公开（公告）日：2004-04-29

  The present invention discloses the identification of the novel inhibitors of IMPDH (inosine-5′-monophosphate dehydrogenase). The compounds and pharmaceutical compositions disclosed herein are useful in treating or preventing IMPDH associated disorders, such as transplant rejection and autoimmune diseases.

  本发明揭示了IMPDH（鸟苷-5'-单磷酸脱氢酶）的新型抑制剂的鉴定。本文所披露的化合物和制药组合物在治疗或预防与IMPDH相关的疾病方面具有用途，例如移植排斥和自身免疫疾病。
• Inhibitors of IMPDH enzyme
  申请人：Bristol-Myers Squibb Co.

  公开号：US07060720B2

  公开（公告）日：2006-06-13

  The present invention discloses the identification of the novel inhibitors of IMPDH (inosine-5′-monophosphate dehydrogenase). The compounds and pharmaceutical compositions disclosed herein are useful in treating or preventing IMPDH associated disorders, such as transplant rejection and autoimmune diseases.

  本发明揭示了新型IMPDH（鸟嘌呤-5'-单磷酸脱氢酶）抑制剂的鉴定。本文所披露的化合物和药物组合物在治疗或预防IMPDH相关疾病方面有用，例如移植排斥和自身免疫疾病。
• Oxamides as IMPDH inhibitors
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1127883A2

  公开（公告）日：2001-08-29

  Disclosed are compounds of the general formula wherein R1represents heterocyclyl; R2represents hydrogen, unsubstituted lower alkyl, lower alkoxy, halo, hydroxy or cyano; R3represents hydrogen, unsubstituted lower alkyl, lower alkoxy, halo, or cyano; R4represents hydrogen, lower alkyl, lower cycloalkyl, aryl, or heterocyclyl; R5represents hydrogen, unsubstituted lower alkyl, lower alkoxy, halo, or cyano; R6represents hydrogen, unsubstituted lower alkyl, lower alkoxy, halo, or cyano; R7represents hydrogen, or unsubstituted lower alkyl; R8represents hydrogen, or unsubstituted lower alkyl; or R4 and R8 together with the nitrogen atom to which they are attached represent heterocyclyl; and pharmaceutically acceptable salts thereof. The disclosed oxamide derivatives are inhibitors of the enzyme inosine monophosphate dehydrogenase (IMPDH). They can be used as medicaments, especially for treating immune mediated conditions or diseases, viral diseases, bacterial diseases, parasitic diseases, inflammation, inflammatory diseases, hyperproliferative vascular diseases, tumours, and cancer. They can be used alone, or in combination with other therapeutically active agents, for example, an immunosuppressant, a chemotherapeutic agent, an anti-viral agent, an antibiotic, an antiparasitic agent, an anti-inflammatory agent, an anti-fungal agent and/or an anti-vascular hyperproliferation agent.

  公开了通式如下的化合物 其中 R1 代表杂环基； R2代表氢、未取代的低级烷基、低级烷氧基、卤代、羟基或氰基 R3 代表氢、未取代的低级烷基、低级烷氧基、卤代物或氰基； R4 代表氢、低级烷基、低级环烷基、芳基或杂环基； R5 代表氢、未取代的低级烷基、低级烷氧基、卤代物或氰基； R6 代表氢、未取代的低级烷基、低级烷氧基、卤代物或氰基； R7 代表氢或未取代的低级烷基 R8 代表氢或未取代的低级烷基； 或 R4 和 R8 与它们所连接的氮原子一起代表杂环基；及其药学上可接受的盐。所公开的草酰胺衍生物是单磷酸肌苷脱氢酶（IMPDH）的抑制剂。它们可用作药物，特别是用于治疗免疫介导的病症或疾病、病毒性疾病、细菌性疾病、寄生虫病、炎症、炎性疾病、过度增生性血管疾病、肿瘤和癌症。它们可以单独使用，也可以与其他具有治疗活性的药物结合使用，例如免疫抑制剂、化疗药物、抗病毒药物、抗生素、抗寄生虫药物、抗炎药物、抗真菌药物和/或抗血管过度增生药物。
• Dual inhibitors of inosine monophosphate dehydrogenase and histone deacetylase based on a cinnamic hydroxamic acid core structure
  作者：Liqiang Chen、Riccardo Petrelli、Guangyao Gao、Daniel J. Wilson、Garrett T. McLean、Hiremagalur N. Jayaram、Yuk Y. Sham、Krzysztof W. Pankiewicz

  DOI：10.1016/j.bmc.2010.06.081

  日期：2010.8

  Small molecules that act on multiple biological targets have been proposed to combat the drug resistance commonly observed for cancer chemotherapy. By combining the structural features of known inhibitors of inosine monophosphate dehydrogense (IMPDH) and histone deacetylase (HDAC), dual inhibitors of IMPDH and HDAC based on the scaffold of cinnamic hydroxamic acid (CHA) have been designed, synthesized, and evaluated in biological assays. Key features, including the linker length, linker functionality, substitution position, and interacting groups, have been explored. Their individual contribution to the inhibitory activities against human IMPDH1 and IMPDH2 as well as HDAC has been assessed. (C) 2010 Elsevier Ltd. All rights reserved.