2-(benzo[d]thiazol-5-yl)benzo[d]oxazole

• 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-(benzo[d]thiazol-5-yl)benzo[d]oxazole
• 英文别名: 2-(benzo[d]thiazol-6-yl)benzo[d]oxazole；2-(1,3-Benzothiazol-6-yl)-1,3-benzoxazole
• 化学式: C₁₄H₈N₂OS
• 分子量: 252.296
• InChiKey: AMRQYLZDLOEZMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-hydroxyphenyl)-1,3-benzothiazole-6-carboxamide 在 Al³⁺ exchanged K₁₀ clay 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 16.0h， 以90%的产率得到2-(benzo[d]thiazol-5-yl)benzo[d]oxazole
  参考文献：
  名称：

  A green route for the synthesis of 2-substituted benzoxazole derivatives catalyzed by Al3+-exchanged K10 clay

  摘要：

  A new, simple, and efficient protocol is developed for the synthesis of 2-substituted benzoxazole derivatives through N-C-O bond formation using Al3+-exchanged K10 clay (Al3+-K10) as catalyst. A wide range of benzoxazole derivatives are synthesized in high yields without affecting many functional groups. Hot filtration experiments showed the absence of metal leaching and catalyst can be reused for five times with only a slight decrease in yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.039

文献信息

• A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates
  作者：Kai Kang、Nathan L. Loud、Tarah A. DiBenedetto、Daniel J. Weix

  DOI：10.1021/jacs.1c10907

  日期：2021.12.29

  medicine and materials science, the synthesis of biheteroaryls by cross-coupling remains challenging. We describe here a new, general approach to biheteroaryls: the Ni- and Pd-catalyzed multimetallic cross-Ullmann coupling of heteroaryl halides with triflates. An array of 5-membered, 6-membered, and fused heteroaryl bromides and chlorides, as well as aryl triflates derived from heterocyclic phenols,

  尽管它们对医学和材料科学很重要，但通过交叉偶联合成双杂芳基仍然具有挑战性。我们在这里描述了一种新的、通用的双杂芳基方法：杂芳基卤化物与三氟甲磺酸酯的 Ni 和 Pd 催化的多金属交叉 Ullmann 偶联。一系列 5 元、6 元和稠合杂芳基溴化物和氯化物，以及衍生自杂环酚的芳基三氟甲磺酸酯，被证明是该反应中可行的底物（62 个示例，平均产率为 63 ± 17%）。这种方法对双杂芳基的普遍性在 10 μmol 规模的 96 孔板格式中得到进一步证明。一组 96 种可能的产品在一组条件下提供了 >90% 的命中率。此外，可以使用配体、添加剂和还原剂的单个“工具箱板”快速优化低产率组合。
• Substituted azetidinyl compounds as GlyT1 inhibitors
  申请人：DART NEUROSCIENCE (CAYMAN) LTD.

  公开号：US10040759B2

  公开（公告）日：2018-08-07

  The invention provides a chemical entity of Formula (I) wherein R1, R2, R3, R4, X, and Y have any of the values described herein, and compositions comprising such chemical entities; methods of making them; and their use in a wide range of methods, including metabolic and reaction kinetic studies; detection and imaging techniques; radioactive treatments; modulating and treating disorders mediated by GlyT1 activity; treating neurological disorders, CNS disorders, dementia, neurodegenerative diseases, and trauma-dependent losses of function; treating stroke, including cognitive and motor deficits during stroke rehabilitation; facilitating neuroprotection and neurorecovery; enhancing the efficiency of cognitive and motor training, including animal skill training; and treating other disorders, including pain and alcohol-dependence.

  本发明提供了式(I)的化学实体，其中 R1、R2、R3、R4、X 和 Y 具有本文所述的任一值，还提供了包含这种化学实体的组合物；制造它们的方法；以及它们在多种方法中的用途，包括代谢和反应动力学研究；检测和成像技术；放射性治疗；调节和治疗由 GlyT1 活性介导的疾病；治疗神经系统疾病、中枢神经系统疾病、痴呆症、神经退行性疾病和创伤依赖性功能丧失；治疗中风，包括中风康复期间的认知和运动障碍；促进神经保护和神经恢复；提高认知和运动训练的效率，包括动物技能训练；以及治疗其他疾病，包括疼痛和酒精依赖。
• Gamma-diketones for treatment and prevention of aging skin and wrinkles
  申请人：Samumed, LLC

  公开号：US10434052B2

  公开（公告）日：2019-10-08

  The present disclosure relates to compounds having the following structure: or a dermatologically acceptable salt thereof, and cosmetic or dermopharmaceutical compositions comprising the same, and methods for using the compounds or compositions for treating, protecting, and/or improving the condition and/or aesthetic appearance of skin, for example, treating, preventing, ameliorating, reducing and/or eliminating fine lines and/or wrinkles of skin, or improving the appearance of fine lines and/or or wrinkles of skin comprising application of the compounds or compositions disclosed.

  本公开涉及具有以下结构的化合物： 或其皮肤学上可接受的盐，以及包含这些化合物的化妆品或皮肤药物组合物，以及使用这些化合物或组合物治疗、保护和/或改善皮肤状况和/或美学外观的方法，例如，治疗、预防、改善、减少和/或消除皮肤细纹和/或皱纹，或改善皮肤细纹和/或或皱纹的外观，包括应用所公开的化合物或组合物。
• Discovery of 2-(2-aminobenzo[d]thiazol-6-yl) benzo[d]oxazol-5-amine derivatives that regulated HPV relevant cellular pathway and prevented cervical cancer from abnormal proliferation
  作者：Peili Jiao、Yuxi Wang、Beibei Mao、Bingding Wang、Yi Zhong、Hongwei Jin、Lihe Zhang、Liangren Zhang、Zhenming Liu

  DOI：10.1016/j.ejmech.2020.112556

  日期：2020.10

  Human papillomavirus (HPV) is a well-established etiological factor for cervical cancer, and the expression of oncogenic protein E7 is crucial for carcinogenesis. Herein, virtual screening was performed and 2-(2-aminobenzo[d]thiazol-6-yl) benzo[d]oxazol-5-amine derivatives were designed, synthesized as antineoplastic agents, and evaluated for their anti-tumor activities. Among them, the most promising compound H1 showed specific anti-proliferation ability against HeLa cells (IC50 = 380 nM) as well as excellent inhibition of tumor growth in the HeLa xenograft model without inducing obvious side effects. It is interesting that compound H1 displayed significant inhibition against HPV18-positive cervical cell lines (HeLa) but not for HPV16-positive cervical cell lines (SiHa). Further study demonstrated that a low concentration of compound H1 could lead to a cell cycle blockage at the G1 phase and promote cell apoptosis slightly (8.77%). Compound H1 also exhibited transcription repression, especially those associated with the oncoprotein E7 cellular pathway like E7/Rb/E2F-1/DNMT1, which were essential in tumorigenesis. Proteomics analysis revealed that E7 might be degraded through E3 ubiquitin ligases, which aligned with decreasing expression of E7 following the treatment of compound H1. Taken together, it indicated that compound H1 could be a promising potential agent for cervical cancer treatment. (C) 2020 Elsevier Masson SAS. All rights reserved.
• SUBSTITUTED AZETIDINYL COMPOUNDS AS GLYT1 INHIBITORS
  申请人：DART NEUROSCIENCE (CAYMAN) LTD.

  公开号：US20170334846A1

  公开（公告）日：2017-11-23

  The invention provides a chemical entity of Formula (I) wherein R 1 , R 2 , R 3 , R 4 , X, and Y have any of the values described herein, and compositions comprising such chemical entities; methods of making them; and their use in a wide range of methods, including metabolic and reaction kinetic studies; detection and imaging techniques; radioactive treatments; modulating and treating disorders mediated by GlyT1 activity; treating neurological disorders, CNS disorders, dementia, neurodegenerative diseases, and trauma-dependent losses of function; treating stroke, including cognitive and motor deficits during stroke rehabilitation; facilitating neuroprotection and neurorecovery; enhancing the efficiency of cognitive and motor training, including animal skill training; and treating other disorders, including pain and alcohol-dependence.