5-chloro-2-phenyloxazolo[5,4-b]pyridine | 1422198-81-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloro-2-phenyloxazolo[5,4-b]pyridine
• 英文别名: 5-chloro-2-phenyl-[1,3]oxazolo[5,4-b]pyridine
• CAS: 1422198-81-9
• 化学式: C₁₂H₇ClN₂O
• 分子量: 230.653
• InChiKey: CRLBMZLNWGKQII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-2-phenyloxazolo[5,4-b]pyridine 在 bis(η3-allyl-μ-chloropalladium(II)) 、 1-deuteriodiphenylmethanol 、 3-(2,6-dibenzhydryl-4-methylphenyl)-4,5-dimethyl-1-(2,4,6-trimethylbenzyl)imidazolium chloride 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以74%的产率得到5-deuterio-2-phenyloxazolo[5,4-b]pyridine
  参考文献：
  名称：

  钯/不对称NHC体系催化的芳基/杂芳基氯化物的氘代脱氯

  摘要：

  利用钯/不对称NHC体系开发了对芳基/杂芳基氯化物的催化氘代脱氯反应，并以高水平的效率，选择性和氘化度实现了将氘精确控制引入各种芳基/杂芳基化合物中的方法。即使在克级合成中，该方法也成功地应用于生物活性剂的转化。Pd-NHC配合物的晶体结构分析导致观察到Pd-芳烃相互作用。

  DOI：

  10.1021/acs.joc.6b01609
• 作为产物：
  描述：

  2,6-二氯-3-氨基吡啶 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 30.0h， 生成 5-chloro-2-phenyloxazolo[5,4-b]pyridine
  参考文献：
  名称：

  Oxazolopyridines and thiazolopyridines as monoamine oxidase B inhibitors for the treatment of Parkinson’s disease

  摘要：

  In Parkinson's disease, the motor impairments are mainly caused by the death of dopaminergic neurons. Among the enzymes which are involved in the biosynthesis and catabolism of dopamine, monoamine oxidase B (MAO-B) has been a therapeutic target of Parkinson's disease. However, due to the undesirable adverse effects, development of alternative MAO-B inhibitors with greater optimal therapeutic potential towards Parkinson's disease is urgently required. In this study, we designed and synthesized the oxazolopyridine and thiazolopyridine derivatives, and biologically evaluated their inhibitory activities against MAO-B. Structure-activity relationship study revealed that the piperidino group was the best choice for the R-1 amino substituent to the oxazolopyridine core structure and the activities of the oxazolopyridines with various phenyl rings were between 267.1 and 889.5 nM in IC50 values. Interestingly, by replacement of the core structure from oxazolopyrine to thiazolopyridine, the activities were significantly improved and the compound in with the thiazolopyridine core structure showed the most potent activity with the IC50 value of 26.5 nM. Molecular docking study showed that van der Waals interaction in the human MAO-B active site could explain the enhanced inhibitory activities of thiazolopyridine derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.066

文献信息

• Anti-inflammatory oxazole[4,5-b]pyridines
  申请人：Merck & Co., Inc.

  公开号：US04038396A1

  公开（公告）日：1977-07-26

  The various isomers of oxazolo- and thiazolopyridines having utility as antiinflammatory, antipyretic and analgesic agents are prepared by condensation of an appropriate amino-hydroxypyridine or amino-mercaptopyridine with a carboxylic acid, halide or anhydride.

  氧唑和噻唑吡啶的各种异构体，具有抗炎、退热和镇痛作用，通过将适当的氨基-羟基吡啶或氨基-巯基吡啶与羧酸、卤化物或酐进行缩合制备。
• PHARMACEUTICAL COMPOSITIONS FOR PREVENTING OR TREATING DEGENERATIVE BRAIN DISEASE AND METHOD OF SCREENING THE SAME
  申请人：LEE Changjoon Justin

  公开号：US20130046093A1

  公开（公告）日：2013-02-21

  A pharmaceutical composition for preventing or treating a degenerative brain disease, and a method of screening a material for preventing or treating a degenerative brain disease. The method may effectively screen a prophylactic or therapeutic candidate material for preventing or treating a degenerative brain disease. A variety of degenerative brain diseases may be effectively prevented or treated using the pharmaceutical composition including a screened material for preventing or treating a degenerative brain disease.

  一种用于预防或治疗退行性脑疾病的药物组合物，以及一种筛选预防或治疗退行性脑疾病材料的方法。该方法可以有效地筛选预防或治疗退行性脑疾病的预防性或治疗性候选材料。使用该药物组合物，包括筛选用于预防或治疗退行性脑疾病的材料，可以有效预防或治疗各种退行性脑疾病。
• Anti-inflammatory oxazolo [5,4-b]pyridines
  申请人：Merck & Co., Inc.

  公开号：US04131677A1

  公开（公告）日：1978-12-26

  The various isomers of oxazolo- and thiazolopyridines having utility as antiinflammatory, antipyretic and analgesic agents are prepared by condensation of an appropriate amino-hydroxypyridine or amino-mercaptopyridine with a carboxylic acid, halide or anhydride.

  具有抗炎、退热和镇痛作用的氧唑烷和噻唑烷吡啶的各种异构体是通过将适当的氨基-羟基吡啶或氨基-巯基吡啶与羧酸、卤化物或酐缩合制备而成。
• Pharmaceutical compositions for preventing or treating degenerative brain disease and method of screening the same
  申请人：Korea Institute of Science and Technology

  公开号：EP2560008A2

  公开（公告）日：2013-02-20

  A pharmaceutical composition for preventing or treating a degenerative brain disease, and a method of screening a material for preventing or treating a degenerative brain disease. The method may effectively screen a prophylactic or therapeutic candidate material for preventing or treating a degenerative brain disease. A variety of degenerative brain diseases may be effectively prevented or treated using the pharmaceutical composition including a screened material for preventing or treating a degenerative brain disease.

  一种用于预防或治疗退行性脑病的药物组合物，以及一种用于预防或治疗退行性脑病的材料筛选方法。 该方法可有效筛选出预防或治疗变性脑病的候选材料。 使用包括经筛选的用于预防或治疗退行性脑病的材料的药物组合物，可有效预防或治疗各种退行性脑病。
• US4038396A
  申请人：——

  公开号：US4038396A

  公开（公告）日：1977-07-26