5-(溴甲基)-3-(4-硝基苯基)异恶唑 | 927188-96-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(溴甲基)-3-(4-硝基苯基)异恶唑
• 英文名称: 5-(bromomethyl)-3-(4-nitrophenyl)isoxazole
• 英文别名: 5-(Bromomethyl)-3-(4-nitrophenyl)-1,2-oxazole；5-(bromomethyl)-3-(4-nitrophenyl)-1,2-oxazole
• CAS: 927188-96-3
• 化学式: C₁₀H₇BrN₂O₃
• 分子量: 283.081
• InChiKey: FXHSJOKOEXARQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(溴甲基)-3-(4-硝基苯基)异恶唑 在 铁粉 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 2,6-difluoro-N-(4-(5-((2,2,2-trifluoroethoxy)methyl)-isoxazol-3-yl)phenylcarbamoyl)benzamide
  参考文献：
  名称：

  Design, Synthesis, and Insecticidal Evaluation of New Benzoylureas Containing Isoxazoline and Isoxazole Group

  摘要：

  Twenty-two new benzoylphenylureas containing isoxazoline and the isoxazole group were designed and synthesized, and their structures were characterized by (1)H NMR and elemental analysis (or FIRMS). The larvicidal activities against Oriental armyworm, mosquito, and diamondback moth of the new compounds were evaluated. Compounds I-1 and III-1 showed nearly the same level of insecticidal activity against Oriental armyworm as commercial insecticide Flucycloxuron and surprisingly exhibited much higher larvicidal activities against diamondback moth than Flucycloxuron.

  DOI：

  10.1021/jf200395g
• 作为产物：
  描述：

  3-(4-nitrophenyl)-5-hydroxymethylisoxazole 在 三溴化磷 作用下， 以 二氯甲烷 为溶剂， 生成 5-(溴甲基)-3-(4-硝基苯基)异恶唑
  参考文献：
  名称：

  新型异恶唑查尔酮衍生物的合成及其对小鼠B16细胞酪氨酸酶和黑色素合成的生物活性，用于治疗白癜风

  摘要：

  一系列新的查耳酮衍生物的1 - 18，轴承异恶唑基部分，设计并合成，和生物学评价其活性对蘑菇酪氨酸酶和鼠B16细胞的黑色素合成。结果表明，大多数制备的化合物的1 - 18对酪氨酸强效的激活作用，特别是对于1 - 2，4，6 - 7，9和15。其中，化合物2，4和9显示出最好的活性，EC 50  = 1.3，2.5和3.0μmol·L-1分别比阳性对照8-甲氧基补骨脂蛋白（8-MOP，EC 50  = 14.8μmol·L -1）好得多；在B16细胞中，所有测试的化合物对黑素生成的活性均强于8-MOP（值为115％）。有趣的是用卤素（取代的衍生物1，2，4，5，7，9）一般是更有效。与8-MOP相比，分别具有3倍和4倍效力的化合物2（463％）和18（438％）被公认为是进一步抗玻璃体药理研究的最有希望的候选药物。

  DOI：

  10.1016/j.bmc.2016.08.066

文献信息

• Safe and Scaleable Oxidation of Benzaldoximes to Benzohydroximinoyl Chlorides^†
  作者：Eric C. Hansen、Mahmut Levent、Terrence J. Connolly

  DOI：10.1021/op100013m

  日期：2010.5.21

  Benzohydroximinoyl chlorides are useful precursors to nitrile oxides used in the preparation of various heterocycles via 1,3-dipolar cycloadditions. These intermediates are typically accessed by oxidation of aldoximes using N-chlorosuccinimide. This simple and efficient reaction is highly exothermic and a significant induction period can be observed. The potential for a sudden and significant heat

  苯氢氧亚甲基酰氯是通过1，3-偶极环加成制备各种杂环中所用的腈氧化物的有用前体。这些中间体通常通过使用N-氯代琥珀酰亚胺氧化醛肟来获得。这种简单而有效的反应是高度放热的，可以观察到明显的诱导期。突然大量释放热量的可能性使大规模反应难以控制，并且具有潜在危险。在本文中，我们描述了此反应的热分析，以确定在常见添加剂存在下的热流，以确定安全放大的最有效方法。在筛选出的添加剂中，HCl水溶液始终避免了诱导期，并使剂量控制过程得以开发。
• A metal-free approach for in situ regioselective synthesis of isoxazoles via 1,3 dipolar cycloaddition reaction of nitrile oxide with propargyl bromide
  作者：Rajeshwar Reddy Aleti、Srinivasulu Cherukupalli、Sanjeev Dhawan、Vishal Kumar、Pankaj S. Girase、Sachin Mohite、Rajshekhar Karpoormath

  DOI：10.1007/s11696-021-02009-8

  日期：2022.5

  Herein, we report a multi-component reaction (MCRs) to synthesise a range of 3-phenyl-5-(bromomethyl)isoxazoles analogues using DMF/water mixture as solvent, providing desired products in good to excellent yields. The reaction efficiently involves the 1,3-dipolar cycloaddition reaction between propargyl bromide and in situ-generated α-chloro aldoximes. The protocol proceeded well under mild metal-free

  在此，我们报告了使用 DMF/水混合物作为溶剂合成一系列 3-苯基-5-(溴甲基)异恶唑类似物的多组分反应 (MCR)，以良好至优异的收率提供所需的产品。该反应有效地涉及炔丙基溴和原位生成的 α-氯醛肟之间的 1,3-偶极环加成反应。该协议在温和的无金属条件下进行得很好，并显示出对多种取代基的耐受性。 图形概要
• 一种查尔酮衍生物的制备方法和用途
  申请人：中国科学院新疆理化技术研究所

  公开号：CN105801509B

  公开（公告）日：2018-01-05

  本发明涉及一种含苯基异噁唑查尔酮衍生物的制备方法和用途，该类化合物以4'‑羟基查尔酮为原料，在碳酸钾的催化下，与不同的3‑取代‑5‑溴甲基异噁唑反应得到。并研究了新化合物对非细胞体系中酪氨酸酶活性及细胞体系中黑素合成的作用。实验结果表明：化合物1、2、4、6、9、15表现出较好的酪氨酸酶激动活性，优于阳性对照8‑甲氧基补骨脂素(8‑MOP)；化合物1、2、4、5、7、9、11、15、16、17、18能够促进B16小鼠细胞中黑素的合成，它们的活性亦优于阳性对照8‑MOP。该方法反应条件温和，实验步骤简捷。通过本发明所述方法获得的含苯基异噁唑的查尔酮衍生物1、2、4、5、6、7、9、11、15、16、17、18均可用于临床上制备治疗白癜风的药物。
• Synthesis of new secretory phospholipase A2-inhibitory indole containing isoxazole derivatives as anti-inflammatory and anticancer agents
  作者：Srinivasa Rao Pedada、Nagendra Sastry Yarla、Pawan J. Tambade、Bhadrapura Lakkappa Dhananjaya、Anupam Bishayee、Kalle M. Arunasree、Gundala Harold Philip、Gangappa Dharmapuri、Gjumrach Aliev、Swathi Putta、Gururaja Rangaiah

  DOI：10.1016/j.ejmech.2016.02.025

  日期：2016.4

  Secretory phospholipase A(2) (sPLA(2)) is an important enzyme that plays a key role in various inflammatory diseases including cancer and its inhibitors have been developed as preventive or therapeutic agents. In the present study, a series of new indole containing isoxazole derivatives (10a-10o) is synthesized and evaluated for their sPLA(2) inhibitory activities. All compounds (10a-10o) showed significant sPLA(2) inhibition activities both in vitro and in vivo studies which is substantiated in in silico studies. Among all the tested compounds, 100 showed potent sPLA(2) inhibition activity, that is comparable or more to ursolic acid (positive control). Further studies demonstrated that 100 showed in vitro antiproliferative activity when tested against MCF-7 breast and DU145 prostate cancer cells. Furthermore, compounds 10a-10o obeyed lipinsky's rule of 5 and suggesting druggable properties. The in vitro, in vivo and in silico results are encouraging and warrant pre-clinical studies to develop sPLA(2)-inhibitory compound 10o as novel therapeutic agent for various inflammatory disorders and several malignancies. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Synthesis and characterization of 2-alkyl -5-{4-[(3-nitrophenyl-5-isoxazolyl)methoxy]phenyl}-2H-tetrazoles
  作者：Y. R. Mirzaei、L. Edjlali

  DOI：10.1007/bf03246058

  日期：2010.9

  Heteroaryl substituted analogs of antirhnoviral (A), was prepared by a convergent approach. 3-Nitrophenyl-5-bromooromethylisoxazoles 5a-b were synthesized by [3+2] cycloaddition of 3-(benzoyloxy)-propyne 2 to in situ generated arylnitrile oxides followed by deprotection of cycloadducts 3a-b and bromination of the resulting alcohols 4a-b. Coupling of 3-nitrophenyl-5-bromooromethylisoxazoles (5a-b) with 4-[5-(2-alkyl-2H-tetrazolyl)]phenols (6a-d) in N-methylpyrrolidinone under mild conditions afforded a new series of 2-alkyl-5-4-[1-(3-nitrophenyl-5-isoxazoly)methyloxy]pheny}-2H-tetrazoles (7a-h) in high yields. The structures of the synthesized compounds were confirmed by their (1)H NMR, Mass spectral, and Elemental Analysis data.