3-(bromomethyl)-4-methyl-1,2,5-oxadiazole-2-oxide | 169614-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(bromomethyl)-4-methyl-1,2,5-oxadiazole-2-oxide
• 英文别名: 3-(bromomethyl)-4-methyl-2-oxido-1,2,5-oxadiazol-2-ium
• CAS: 169614-77-1
• 化学式: C₄H₅BrN₂O₂
• 分子量: 193.0
• InChiKey: KMISEZWGSVPVSG-UHFFFAOYSA-N

物化性质

• 沸点：
  269.6±32.0 °C(Predicted)
• 密度：
  1.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(bromomethyl)-4-methyl-1,2,5-oxadiazole-2-oxide 在 calcium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以95%的产率得到3-(hydroxymethyl)-4-methyl-1,2,5-oxadiazole-2-oxide
  参考文献：
  名称：

  Gasco, Andrea Marcello; Boschi, Donatella; Gasco, Alberto, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 811 - 814

  摘要：

  DOI：
• 作为产物：
  描述：

  4-bromomethyl-3-methylfuroxan 以 various solvent(s) 为溶剂， 反应 24.0h， 生成 3-(bromomethyl)-4-methyl-1,2,5-oxadiazole-2-oxide
  参考文献：
  名称：

  Gasco, Andrea Marcello; Boschi, Donatella; Gasco, Alberto, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 811 - 814

  摘要：

  DOI：

文献信息

• 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 (
• [EN] DRUGS DERIVED FROM DICLOFENAC CONTAINING NO-DONOR HETEROCYCLES, COMPOSITION AND METHOD OF INFLAMMATION TREATMENT<br/>[FR] MEDICAMENTS DERIVES DU DICLOFENAC, CONTENANT DES HETEROCYCLES DONNEURS DE NO, COMPOSITION ET METHODE DE TRAITEMENT DES INFLAMMATIONS
  申请人：CMAX OTIMIZACAO DE RESULTADOS

  公开号：WO2006042387A1

  公开（公告）日：2006-04-27

  The present invention refers to drugs resulting from the pharmaceutical substance diclofenac, relative to the formula. The invention further refers to a pharmaceutical composition, which involves the said drugs and a pharmaceutically adequate vehicle. It is also described a method for the treatment of inflammation through the administration of the new drugs in patients with gastric problems or subjected to long-term treatments.

  本发明涉及与制药物质双氯芬酸有关的药物，相对于该化学式。该发明还涉及一种制药组合物，其中包括所述药物和药学上适当的载体。还描述了一种通过在患有胃部问题或接受长期治疗的患者中施用新药物来治疗炎症的方法。
• Synthesis of Ursolic Acid Conjugates Containing a Furoxan Moiety
  作者：S. A. Popov、L. M. Kornaukhova、A. V. Shpatov、I. A. Grigor’ev

  DOI：10.1007/s10600-016-1708-2

  日期：2016.5

  increased anti-inflammatory activity [3]. Derivatives of 1,2,5-oxadiazole-2-oxide (furoxan) can be used as the NO donor. The synthesis of the conjugate of diclofenac and a furoxan derivative that exhibited high anti-inflammatory activity was reported [4]. Furoxan derivatives have been reported to have also antithrombotic [5], vasodilating [6], and bactericidal [7] activities. According to the literature

  近来，非甾体抗炎药（NSAIDs）联合NO供体（NO-NSAIDs）引起了人们的关注，被认为是有前途的抗癌化疗药物[1]。与普通NSAIDs相比，NO-NSAIDs毒性低，副作用少，尤其是对胃肠道和肾脏的损害[2]。在与非甾体抗炎药的杂交中使用 NO 供体可产生协同作用并增加抗炎活性 [3]。1,2,5-oxadiazole-2-oxide (furoxan) 的衍生物可用作 NO 供体。据报道，双氯芬酸和呋喃烷衍生物的结合物的合成具有很高的抗炎活性[4]。据报道，呋喃西林衍生物还具有抗血栓形成 [5]、血管舒张 [6] 和杀菌 [7] 活性。据文献记载，微毒的熊果酸 (UA) 及其几种衍生物也具有显着的抗炎活性 [8]。UrSAne 型化合物作为潜在的抗癌化疗药物正在被积极研究。制备了 UA 琥珀酸酯和呋喃衍生物的结合物 [9]。一些新化合物表现出超过 UA 和 5-氟尿嘧啶的细胞毒活性。在这里，我们交流了
• Lupane-type conjugates with aminoacids, 1,3,4- oxadiazole and 1,2,5-oxadiazole-2-oxide derivatives: Synthesis, anti-inflammatory activity and in silico evaluation of target affinity
  作者：Sergey A. Popov、Marya D. Semenova、Dmitry S. Baev、Irina V. Sorokina、Natalya A. Zhukova、Tatyana S. Frolova、Tatyana G. Tolstikova、Elvira E. Shults、Māris Turks

  DOI：10.1016/j.steroids.2019.108443

  日期：2019.10

  With the purpose to improve anti-inflammatory activity, the impact of introduction of 1,2,5- and 1,3,4-oxadiazole fragments to betulonic acid core as well as hybrids tethered with short to-amino acids has been studied. The anti-inflammatory activity of synthesized compounds was tested in vivo using models of inflammation induced by concanavalin A and histamine. The majority of new compounds demonstrated higher anti-inflammatory activity compared with starting betulonic acid. To confirm the molecular targets of new derivatives in NRf2 and NF kappa B pathways the docking at Kelch and BTB active sites of Keap1 as well as IKK was done. The novelty of the present work is the development of new class of low toxic anti-inflammatory substances consisting of amino acid-linked betulonic acid - oxadiazole conjugates. These compounds can be considered as prospective chemopreventive agents.
• Synthesis of Conjugates of Ursolic Acid 3-O-Succinate with NO-H2S Donors
  作者：S. A. Popov、L. M. Kornaukhova、A. V. Shpatov、I. A. Grigor’ev

  DOI：10.1007/s10600-017-2061-9

  日期：2017.5