2-(azidomethyl)-5-phenyl-1,3,4-oxadiazole | 934638-47-8

• 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-(azidomethyl)-5-phenyl-1,3,4-oxadiazole
• CAS: 934638-47-8
• 化学式: C₉H₇N₅O
• 分子量: 201.187
• InChiKey: ZKCXVAOHCKWKTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(azidomethyl)-5-phenyl-1,3,4-oxadiazole 在 盐酸 、 三苯基膦 作用下， 以 乙醚 、 水 、 乙酸乙酯 为溶剂， 反应 25.0h， 以73%的产率得到1-(5-苯基-1,3,4-恶二唑-2-基)甲胺盐酸盐(1:1)
  参考文献：
  名称：

  从可用的氯甲基-1,3,4 / 1,2开始，一锅CuAAC合成（1H-1,2,3-三唑-1-基）甲基-1,3,4 / 1,2,4-恶二唑， 4-恶二唑

  摘要：

  一锅法CuAAC合成（1 H -1,2,3-三唑-1基）甲基-1,3,4-恶二唑和（1 H -1,2,3-三唑-1基）甲基研究了通过与叠氮化物的随后亲核取代氯反应的三组分反应制得的1,2,4-恶二唑衍生物，以及在CuI存在下与炔烃进行的进一步“点击”反应。探索了新合成的2-（叠氮甲基）-1,3,4 / 1,2,4-恶二唑和氯甲基-1,3,4 / 1,2,4-恶二唑衍生物的效用，并确定了它们的局限性。新型5-（[[4-芳基-1 H -1,2,3-三唑-1-基]甲基] -3-（芳基）-1,2,4-恶二唑，2-（[4-芳基-1以高收率获得了H -1,2,3-三唑-1-甲基] -5-（芳基）-1,3,4-恶二唑。

  DOI：

  10.1002/jhet.4008
• 作为产物：
  描述：

  5-苯基四氮唑 在 sodium azide 、 苄基三乙基氯化铵 作用下， 以 水 、 甲苯 为溶剂， 生成 2-(azidomethyl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Polynuclear nonfused tetrazole-, 1,3,4-oxadiazole-, and 1,2,3-triazole-containing systems

  摘要：

  Polynuclear nonfused blocks containing 1,2,3-triazole, 1,3,4-oxadiazole, and tetrazole rings were synthesized by reaction of C-substituted tetrazoles with carboxylic acid chlorides, as well as by cycloaddition of 2-azidomethyl-1,3,4-oxadiazoles at the triple bond of acetylenic compounds.

  DOI：

  10.1134/s1070428006060170

文献信息

• Regioselective Approach to 5-Carboxy-1,2,3-triazoles Based on Palladium-Catalyzed Carbonylation
  作者：Gennadij Latyshev、Yury Kotovshchikov、Irina Beletskaya、Nikolay Lukashev

  DOI：10.1055/s-0036-1591896

  日期：2018.5

  3-triazoles based on palladium-catalyzed carbonylation has been developed. The protocol utilizes readily available 5-iodotriazoles as starting materials. The obtained products were used in the syntheses of fused heterocycles as well as derivatization of the steroidal hormone cortexolone­. A regioselective two-step approach to 5-carboxy-1,2,3-triazoles based on palladium-catalyzed carbonylation has been developed

  摘要 已经开发了基于钯催化的羰基化的5-羧基-1,2,3-三唑的区域选择性两步法。该方案利用容易获得的5-碘三唑作为起始原料。所得产物用于稠合杂环的合成以及甾体激素皮质酮的衍生化。 已经开发了基于钯催化的羰基化的5-羧基-1,2,3-三唑的区域选择性两步法。该方案利用容易获得的5-碘三唑作为起始原料。所得产物用于稠合杂环的合成以及甾体激素皮质酮的衍生化。
• Selective Synthesis of Functionally Substituted 1,2,3-Triazoles
  作者：T. V. Golobokova、A. G. Proidakov、V. N. Kizhnyaev

  DOI：10.1134/s1070428020030136

  日期：2020.3

  AbstractDifferent conditions were used to achieve selective formation of 4.5-disubstituted 1-aryl(hetaryl)-1,2,3-triazoles via cycloaddition of the corresponding enolates and aryl or hetaryl azides. Optimal conditions were found for the bromination of 1-(5-methyl-1-phenyl-1,2,3-triazol-4-yl)ethanone to obtain 2-bromo-1-(5-methyl-1-phenyl-1,2,3-triazol-4-yl)ethanone.

  摘要通过相应的烯醇化物和芳基或杂芳基叠氮化物的环加成反应，使用不同的条件来实现4.5-二取代的1-芳基（杂芳基）-1,2,3-三唑的选择性形成。找到了最佳的条件来溴化1-（5-甲基-1-苯基-1,2,3-三唑-4-基）乙酮以获得2-溴-1-（5-甲基-1-苯基-1） ，2,3-三唑-4-基）乙酮。
• Synthesis and cytotoxicity of hybrids of 1,3,4- or 1,2,5-oxadiazoles tethered from ursane and lupane core with 1,2,3-triazole
  作者：Sergey A. Popov、Marya D. Semenova、Dmitry S. Baev、Tatiana S. Frolova、Michael A. Shestopalov、Chengzhang Wang、Zhiwen Qi、Elvira E. Shults、Māris Turks

  DOI：10.1016/j.steroids.2020.108698

  日期：2020.10

  linked to C-28 position of triterpene backbone demonstrated marked cytotoxic activity towards MCF-7 and HepG2 cells. The most active ester of ursolic acid with (1-((4-methyl-2-oxido-1,2,5-oxadiazol-3-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl substituent and 3-O-acetyl group was superior in activity and selectivity over doxorubicin and ursolic acid on MCF-7 cells. The length of the carbon spacer group may be

  Ursane 和 lupane 型（1-（（5-芳基-1,3,4-恶二唑-2-基）甲基）-1H-1,2,3-三唑-4-基）甲基和（1-（（4 -methyl-2-oxido-1,2,5-oxadiazol-3-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl 杂化物是通过 1,3-环加成反应制备的 唑-衍生的叠氮化物具有连接到三萜核心的 C-3 和 C-28 位的炔酯，并测试了细胞毒性。1,3,4-恶二唑的杂合化合物连接在三萜骨架的 3-和 28- 位上通过三唑间隔基和 1,2,5-恶二唑或 1,3,4-恶二唑的组合，与琥珀酸酯接头和 1,2 相连， 3-三唑在乌苏烷骨架的位置3-，是相对于所有测试的癌细胞不活动的。最终，呋喃烷片段和连接到三萜骨架 C-28 位置的 1,2,3-三唑的组合显示出对 MCF-7 和 HepG2 细胞的显着细胞毒活性。熊果酸与 (
• Discovery of novel heteroarylmethylcarbamodithioates as potent anticancer agents: Synthesis, structure-activity relationship analysis and biological evaluation
  作者：Ying-Bo Li、Xu Yan、Ri-Dong Li、Peng Liu、Shao-Qian Sun、Xin Wang、Jing-Rong Cui、De-Min Zhou、Ze-Mei Ge、Run-Tao Li

  DOI：10.1016/j.ejmech.2016.02.015

  日期：2016.4

  further mechanistic study showed that it induced apoptosis and cell cycle arrest through disrupting spindle assembly in mitotic progression, indicating these synthesized dithiocarbamates represented a novel series of anti-cancer compounds targeting mitosis.

  设计，合成和评估了一系列基于铅化合物10结构的新类似物，它们针对四种选定的人类癌细胞系（HL-60，Bel-7402，SK-BR-3和MDA）的体外抗癌活性-MB-468）。与铅化合物10相比，几种合成的化合物表现出改善的抗癌活性。其中，1,3,4-恶二唑类似物17o对Bel-7402，SK-BR-3和MDA-MB-468细胞表现出最高的生物活性，IC 50值分别为1.23、0.58和4.29μM。值得注意的是17o具有对癌细胞的有效抗增殖活性，对非恶性细胞的细胞毒性相对较小。进一步的机理研究表明，它通过破坏有丝分裂进程中的纺锤体组装诱导细胞凋亡和细胞周期停滞，表明这些合成的二硫代氨基甲酸酯代表了一系列针对有丝分裂的新型抗癌化合物。
• Synthesis of variously coupled conjugates of d-glucose, 1,3,4-oxadiazole, and 1,2,3-triazole for inhibition of glycogen phosphorylase
  作者：Sándor Kun、Gergő Z. Nagy、Marietta Tóth、Laura Czecze、Albert Nguyen Van Nhien、Tibor Docsa、Pál Gergely、Maria-Despoina Charavgi、Paraskevi V. Skourti、Evangelia D. Chrysina、Tamás Patonay、László Somsák

  DOI：10.1016/j.carres.2011.03.004

  日期：2011.9

  5-(O-Perbenzoylated-beta-D-glucopyranosyl)tetrazole was obtained from O-perbenzoylated-beta-D-glucopyranosyl cyanide by Bu3SnN3 or Me3SiN3-Bu2SnO. This tetrazole was transformed into 5-ethynyl- as well as 5-chloromethyl-2-(O-perbenzoylated-beta-D-glucopyranosyl)-1,3,4-oxadiazoles by acylation with propiolic acid-DCC or chloroacetyl chloride, respectively. The chloromethyl oxadiazole gave the corresponding azidomethyl derivative on treatment with NaN3. These compounds were reacted with several alkynes and asides under Cu(I) catalysed cycloaddition conditions to give, after removal of the protecting groups by the Zemplen protocol, beta-D-glucopyranosyl-1,3,4-oxadiazolyl-1,2,3-triazole, beta-D-glucopyranosyl-1,2,3-triazolyl-1,3,4-oxadiazole, and beta-D-glucopyranosyl-1,3,4-oxadiazolylmethyl-1,2,3-triazole type compounds. 5-Phenyltetrazole was also transformed under the above conditions into a series of aryl-1,3,4-oxadiazolyl-1,2,3-triazoles, aryl-1,2,3-triazolyl-1,3,4-oxadiazoles, and aryl-1,3,4-oxadiazolylmethyl-1,2,3-triazoles. The new compounds were assayed against rabbit muscle glycogen phosphorylase b and the best inhibitors had inhibition constants in the upper micromolar range (2-phenyl-5-[1-(beta-D-glucopyranosyl)-1,2,3-triazol-4-yl]-1,3,4-oxadiazole 36: K-i = 854 mu M, 2-(beta-D-glucopyranosyl)-5-[1-(naphthalen-2-yl)-1,2,3-triazol-4-yl]-1,3,4-oxadiazole 47: K-i = 745 mu M). (C) 2011 Elsevier Ltd. All rights reserved.