2-azido-1-m-tolylethanone | 215320-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-1-m-tolylethanone
• 英文别名: 2-azido-1-(m-tolyl)ethan-1-one；2-Azido-1-(3-methylphenyl)ethanone；2-azido-1-(3-methylphenyl)ethanone
• CAS: 215320-54-0
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: VLVNLQSEVADFHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethoxy-8-isothiocyanato-1,4-dihydronaphthalene 、 2-azido-1-m-tolylethanone 在 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 N-(7-ethoxy-5,8-dihydronaphthalen-1-yl)-5-(3-methylphenyl)-1,3-oxazol-2-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-substituted and 4,5-disubstituted-2-arylamino oxazole TRPV1 antagonists

  摘要：

  The synthesis and structure-activity relationships of a series of 5-monosubstituted and 4,5-disubstituted 2-arylaminooxazoles as novel antagonists of the transient receptor potential vanilloid 1 (TRPV1) receptor are described. The 7-hydroxy group of the tetrahydronaphthyl moiety on the 2-amino substituent of the oxazole ring was important for obtaining excellent in vitro potency at the human TRPV1 receptor, while a variety of alkyl and phenyl substituents at the 4- and 5-positions of the oxazole ring were well tolerated and yielded potent TRPV1 antagonists. Despite excellent in vitro potency, the 5-monosubstituted compounds suffered from poor pharmacokinetics. It was found that 4,5-disubstitution on the oxazole ring was critical to the improvement of the overall pharmacokinetic profile of these analogues, which led to the discovery of compound (R)-27, a novel TRPV1 antagonist with good oral activity in preclinical animal models of pain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.099
• 作为产物：
  描述：

  2-溴-1-间甲苯-乙酮 在 sodium azide 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 2-azido-1-m-tolylethanone
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-substituted and 4,5-disubstituted-2-arylamino oxazole TRPV1 antagonists

  摘要：

  The synthesis and structure-activity relationships of a series of 5-monosubstituted and 4,5-disubstituted 2-arylaminooxazoles as novel antagonists of the transient receptor potential vanilloid 1 (TRPV1) receptor are described. The 7-hydroxy group of the tetrahydronaphthyl moiety on the 2-amino substituent of the oxazole ring was important for obtaining excellent in vitro potency at the human TRPV1 receptor, while a variety of alkyl and phenyl substituents at the 4- and 5-positions of the oxazole ring were well tolerated and yielded potent TRPV1 antagonists. Despite excellent in vitro potency, the 5-monosubstituted compounds suffered from poor pharmacokinetics. It was found that 4,5-disubstitution on the oxazole ring was critical to the improvement of the overall pharmacokinetic profile of these analogues, which led to the discovery of compound (R)-27, a novel TRPV1 antagonist with good oral activity in preclinical animal models of pain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.099

文献信息

• Visible-light-enabled oxyazidation of alkenes leading to α-azidoketones in air
  作者：Wei Wei、Huanhuan Cui、Huilan Yue、Daoshan Yang

  DOI：10.1039/c8gc01245h

  日期：——

  Visible-light-induced oxyazidation of alkenes for the construction of α-azidoketones has been developed at room temperature in air.

  可见光诱导的烯烃氧化反应可在室温下在空气中进行，用于合成α-叠氮酮。
• 基于光催化的制备ɑ-叠氮酮化合物的方法
  申请人：曲阜师范大学

  公开号：CN108586283B

  公开（公告）日：2021-01-15

  一种基于光催化制备ɑ‑叠氮酮化合物的方法，基于下述反应式：其中R1为任意取代的芳基、杂芳基、1‑12碳烷基；R2为任意取代的芳基、杂芳基、或1‑12碳烷基、氢原子。通式I所示的物设置为烯烃,通式II所示的物设置为叠氮基三甲基硅烷(TMSN3)，通式III所示的物设置为ɑ‑叠氮酮化合物，采用在可见光催化下合成ɑ‑叠氮酮化合物。由于设计了光催化剂，采用在可见光催化下，以空气为氧化剂合成ɑ‑叠氮酮化合物，不再使用当量的无机氧化剂、金属试剂、以及预先制备复杂的原料，因此降低了反应条件，提高了反应的安全性。
• Synthesis and In vitro Evaluation of Dibenzoazepine Triazole Derivatives: A Novel Class of Antileishmanial Agents
  作者：Maria Aqeel Khan、Aliyan Saleem、Nida Ghouri、Abdul Hameed、M. Choudhary、Fatima Basha

  DOI：10.2174/1570180812999150225111959

  日期：2015.6.6

  In the present study, a series of dibenzoazepine triazole derivatives (24-39) were synthesized and evaluated for their in vitro bioactivities including antiglycation, antibacterial, DPPH radical scavenging, urease inhibition, antileishmanial and immunomodulatory activities. The compounds were found to be moderately active only against leishmania. Within this series, compound 26 was found to be the most active antileishaminals with IC50 value 37.4 ± 0.4 µM. Structure-activity relationships for this novel class are discussed.

  在本研究中，合成了一系列二苯并氮杂卓三唑衍生物（24-39），并评估了它们的体外生物活性，包括抗糖基化、抗菌、DPPH自由基清除、尿素酶抑制、抗利什曼和免疫调节活性。这些化合物仅对利什曼原虫表现出适度的活性。在这一系列中，化合物26被发现是活性最强的抗利什曼药物，IC50值为37.4 ± 0.4 µM。对这一新型化合物的构效关系进行了讨论。
• Synthesis of α-Amidoketones through the Cascade Reaction of Carboxylic Acids with Vinyl Azides under Catalyst-Free Conditions
  作者：Cai Gao、Qianting Zhou、Li Yang、Xinying Zhang、Xuesen Fan

  DOI：10.1021/acs.joc.0c01871

  日期：2020.11.6

  An efficient synthesis of α-amidoketone derivatives through the cascade reactions of carboxylic acids with vinyl azides is presented. Compared with literature protocols, notable features of this new method include catalyst-free conditions, broad substrate scope, good tolerance of a wide range of functional groups, and high efficiency. In addition, the synthetic potential of this method as a tool for

  提出了通过羧酸与叠氮化乙烯的级联反应有效合成α-酰胺酮衍生物的方法。与文献方法相比，该新方法的显着特征包括无催化剂条件，广泛的底物范围，对各种官能团的良好耐受性和高效率。另外，该方法作为后期修饰工具的合成潜力通过其在许多羧酸药物分子的结构修饰中的应用而令人信服。
• In vitro α-Glucosidase Inhibition by Non-sugar based Triazoles of Dibenzoazepine, their Structure-Activity Relationship, and Molecular Docking
  作者：Maria A. Khan、Kulsoom Javaid、Abdul Wadood、Alam Jamal、Farhana Batool、Saba Fazal-ur-Rehman、Fatima Z. Basha、Muhammad I. Choudhary

  DOI：10.2174/1573406413666170726142949

  日期：2017.10.17

  Background: α-Glucosidase inhibitors (AGIs) have been reported for their clinical potential against postprandial hyperglycemia, which is responsible for the risks associated with diabetes mellitus 2 and cardiovascular diseases (CVDs). Besides, a number of compounds have been reported as potent AGIs, several side effects are associated with them. Methods: The aim of present work is to explore new and potent molecules as AGIs. Therefore, a library of dibenzoazepine linked triazoles (1-15) was studied for their in vitro α-glucosidase inhibitory activity. The binding modes of potent compounds in the active site of α-glucosidase enzyme were also explored through molecular docking studies. Results and Conclusion: Among the reported triazoles, compounds 3-9, 11, and 13 (IC50 = 6.0 ± 0.03 to 19.8 ± 0.28 µM) were found to be several fold more active than the standard drug acarbose (IC50 = 840 ± 1.73 µM). Compound 5 (IC50 = 6.0 ± 0.03 µM) was the most potent AGIs in the series, about 77- fold more active than acarbose. Therefore, dibenzoazepine linked-triazoles described here can serve as leads for further studies as new non-sugar AGIs.

  背景：α-葡萄糖苷酶抑制剂（AGIs）在对抗餐后高血糖方面显示出临床潜力，而餐后高血糖与2型糖尿病和心血管疾病（CVDs）的风险相关。此外，已经报告有多种化合物作为有效的AGIs，但它们也伴随一些副作用。 方法：本研究的目的是探索新的有效分子作为AGIs。因此，研究了一个含有二苯并氮杂环的三唑化合物库（1-15）对α-葡萄糖苷酶的体外抑制活性。还通过分子对接研究探索了这些有效化合物在α-葡萄糖苷酶酶活性位点的结合方式。 结果与结论：在报告的三唑化合物中，化合物3-9、11和13（IC50 = 6.0 ± 0.03至19.8 ± 0.28 µM）比标准药物阿卡波糖（IC50 = 840 ± 1.73 µM）活性高出数倍。化合物5（IC50 = 6.0 ± 0.03 µM）是系列中最有效的AGIs，大约比阿卡波糖活性高出77倍。因此，这里描述的二苯并氮杂环连接的三唑化合物可以作为新型非糖AGIs进一步研究的先导。