2-(1-adamantyl)-5-(4-bromophenyl)-1,3,4-oxadiazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(1-adamantyl)-5-(4-bromophenyl)-1,3,4-oxadiazole
• 英文别名: 2-(4-Bromophenyl)-5-(tricyclo[3.3.1.1~3,7~]dec-1-yl)-1,3,4-oxadiazole
• 化学式: C₁₈H₁₉BrN₂O
• 分子量: 359.266
• InChiKey: OWSODSGJSXHARF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对溴苯甲酰肼 在 吡啶 、 三氯氧磷 作用下， 反应 1.5h， 生成 2-(1-adamantyl)-5-(4-bromophenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  新型2-（1-金刚烷基）-5-取代-1,3,4-恶二唑和2-（1-金刚烷基氨基）-5-取代-1,3,4-噻二唑的合成，抗菌和抗炎活性。

  摘要：

  1-金刚烷羰基氯与某些羧酸酰肼在吡啶中反应，生成相应的N-酰基金刚烷-1-碳酰肼衍生物3a-j，将其环化为相应的2-（1-金刚烷基）-5-取代的-1,3 ，4-恶二唑4a-j通过与三氯氧化磷一起加热。用乙醇中的某些羧酸酰肼处理1-金刚烷基异硫氰酸酯产生相应的1-酰基-4-（1-金刚烷基）-3-硫代半氨基叠氮化物7a-g，将其环化为相应的2-（1-金刚烷基氨基）-5-取代的1,3,4-噻二唑衍生物8a-g。测试了化合物4a-j，7a-g和8a-g对一组革兰氏阳性和革兰氏阴性细菌以及酵母样致病真菌白色念珠菌的体外活性。几种衍生物产生了良好或中等的活性，特别是针对被测革兰氏阳性细菌枯草芽孢杆菌。同时，化合物4i和8g显示出对白色念珠菌的显着抗真菌活性。另外，使用角叉菜胶诱导的爪水肿方法在大鼠中测定了合成化合物的体内抗炎活性。恶二唑衍生物4c，4g，4i和4j产生了良好的剂量依赖性抗炎活性。

  DOI：

  10.1016/j.ejmech.2006.10.003

文献信息

• Synthesis, Crystal Structure and Anti-HIV Activity of 2- Adamantyl/adamantylmethyl-5-aryl-1,3,4-oxadiazoles
  作者：Mahmood-ul-Hassan Khan、Tashfeen Akhtar、Najim A. Al-Masoudi、Helen Stoeckli-Evans、Shahid Hameed

  DOI：10.2174/1573406411208061190

  日期：2012.9.1

  Two series of 2-adamantyl/adamantylmethyl-5-aryl-1,3,4-oxadiazoles (4a-l and 5a-l) were synthesized by cyclodehydration of adamantan-1-carboxylic acid/adamantylacetic acid with various aryl hydrazides (3a-l) in the presence of POCl3. The synthesis was supported by spectroanalytical techniques and verified further by crystal structure determination of compounds 4e and 5k. The synthesized compounds were screened for their inhibitory activity against HIV-1 and HIV-2 in MT-4 cells. Compound 5b exhibited a moderate activity in vitro for the replication of both virus types, suggesting for further structural modification as a new lead in the development of an antiviral agent.

  合成了两系列的2-氨基-邻氨基-5-芳基-1,3,4-噁二唑（4a-l和5a-l），通过在POCl3的存在下，将亚甲基氨基-1-羧酸/亚甲基氨基乙酸与各种芳基肼（3a-l）进行环脱水反应。合成过程得到了光谱分析技术的支持，并通过化合物4e和5k的晶体结构测定进一步验证。合成的化合物在MT-4细胞中筛选其对HIV-1和HIV-2的抑制活性。化合物5b在体外对两种病毒类型的复制表现出适度活性，建议对其进行进一步的结构修饰，以作为开发抗病毒药物的新线索。
• 2-Substituted thiazolidinone and oxazolidinone derivatives for the inhibition of phosphatases and the treatment of cancer
  申请人：——

  公开号：US20040097566A1

  公开（公告）日：2004-05-20

  The present invention relates to certain substituted heterocycles, including 2-substituted thiazolidinone and 2-substituted oxazolidinone compounds. These compounds are useful in the treatment of diseases related to uncontrolled cellular proliferation, such as cancer or precancerous conditions. The compounds are also useful for modulating lipid and/or carbohydrate metabolism, and treating Type II diabetes, hyperglycemia or obesity, and for treating inflammatory diseases such as arthritis. Some disclosed embodiments of the invention relate to compounds having the structures indicated below, or a pharmaceutically acceptable salt thereof. 1

  本发明涉及某些取代杂环化合物，包括2-取代噻唑烷酮和2-取代噁唑烷酮化合物。这些化合物在治疗与细胞无法控制增殖相关的疾病，如癌症或癌前病变方面非常有用。这些化合物还可用于调节脂质和/或碳水化合物代谢，治疗II型糖尿病、高血糖或肥胖症，以及治疗炎症性疾病，如关节炎。本发明的某些实施例涉及具有下面所示结构的化合物或其药学上可接受的盐。1
• Khan, Mahmood-Ul-Hassan; Akhtar, Tashfeen; Al-Masoudi, Najim A., Medicinal Chemistry, 2012, vol. 8, # 6, p. 1190 - 1197
  作者：Khan, Mahmood-Ul-Hassan、Akhtar, Tashfeen、Al-Masoudi, Najim A.、Stoeckli-Evans, Helen、Hameed, Shahid

  DOI：——

  日期：——
• 2-SUBSTITUTED THIAZOLIDINONE AND OXAZOLIDINONE DERIVATIVES FOR THE INHIBITION OF PHOSPHATASES AND THE TREATMENT OF CANCER
  申请人：Incyte San Diego Incorporated

  公开号：EP1463718A1

  公开（公告）日：2004-10-06
• [EN] 2-SUBSTITUTED THIAZOLIDINONE AND OXAZOLIDINONE DERIVATIVES FOR THE INHIBITION OF PHOSPHATASES AND THE TREATMENT OF CANCER<br/>[FR] DERIVES THIAZOLIDINONE ET OXAZOLIDINONE 2-SUBSTITUES POUR L'INHIBITION DES PHOSPHATASES ET LE TRAITEMENT DU CANCER
  申请人：MAXIA PHARMACEUTICALS INC

  公开号：WO2003050098A1

  公开（公告）日：2003-06-19

  The present invention relates to certain substituted heterocycles, including 2-substituted thiazolidinone and 2-substituted oxazolidinone compounds. These compounds are useful in the treatment of diseases related to uncontrolled cellular proliferation, such as cancer or precancerous conditions. The compounds are also useful for modulating lipid and/or carbohydrate metabolism, and treating Type lI diabetes, hyperglycemia or obesity, and for treating inflammatory diseases such as arthritis. Some disclosed embodiments of the invention relate to compounds having the structures indicated below, or a pharmaceutically acceptable salt thereof, Formula (I) or (II).