4-(bromomethyl)furoxan-3-carbonitrile | 579463-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(bromomethyl)furoxan-3-carbonitrile
• 英文别名: 4-(Bromomethyl)-2-oxido-1,2,5-oxadiazol-2-ium-3-carbonitrile
• CAS: 579463-37-9
• 化学式: C₄H₂BrN₃O₂
• 分子量: 203.983
• InChiKey: TYZFHTMHKWKXON-UHFFFAOYSA-N

物化性质

• 沸点：
  339.0±50.0 °C(Predicted)
• 密度：
  2.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  阿齐沙坦 、 4-(bromomethyl)furoxan-3-carbonitrile 在 三乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 4-(3-cyano-1,2,5-oxadiazole-2-oxide)methyl 2-ethoxy-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate
  参考文献：
  名称：

  苯并咪唑衍生物及其制备方法和医药用途

  摘要：

  本发明属于药物化学技术领域，具体公开了一类苯并咪唑衍生物及其制备方法和医药用途。苯并咪唑衍类生物包括川芎嗪和NO供体类衍生物，该类化合物在体内迅速释放出川芎嗪或NO，从而与阿齐沙坦发生有效的协同作用，增强抗高血压疗效，减少不良反应，对患者肝肾具有较理想的保护作用，填补了现有技术中的空白。

  公开号：

  CN105237527B
• 作为产物：
  描述：

  1,2,5-恶二唑-3-甲酰胺,4-(溴甲基)--2,2-氧化物 在 trifluoromethanesulfonic acid anhydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以75%的产率得到4-(bromomethyl)furoxan-3-carbonitrile
  参考文献：
  名称：

  Rolando, Barbara; Cena, Clara; Caron, Giulia, Medicinal Chemistry Research, 2002, vol. 11, # 6, p. 322 - 332

  摘要：

  DOI：

文献信息

• New furoxan derivatives for the treatment of ocular hypertension
  作者：Marco Blangetti、Barbara Rolando、Konstantin Chegaev、Stefano Guglielmo、Loretta Lazzarato、Mariaconcetta Durante、Emanuela Masini、Nicoletta Almirante、Elena Bastia、Francesco Impagnatiello、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/j.bmcl.2016.12.041

  日期：2017.2

  A small series of water-soluble NO-donor furoxans bearing a basic center at the 4-position, having a wide lipophilic-hydrophilic balance range, and endowed with different NO-release capacities, were synthesized and characterized. Selected members were studied for their IOP-lowering activity in the transient ocular hypertensive rabbit model at 1% dose. The most effective IOP-lowering products were compounds

  合成并表征了一系列小分子的水溶性NO供体呋喃烷，它们在4位具有一个基本中心，具有宽的亲脂亲水性平衡范围，并具有不同的NO释放能力。研究所选成员在短暂性高眼压兔模型中1％剂量下降低IOP的活性。降低IOP的最有效产品是化合物3和7，给药60分钟后的活性与Timolol相似。值得注意的是，7具有持久作用。该系列产品中降低IOP的活性似乎是由亲脂-亲水平衡而不是由NO供体的能力调节的。
• Benzimidazole Derivatives and Preparation Process and Pharmaceutical Uses Thereof
  申请人：WUHAN LL SCIENCE AND TECHNOLOGY DEVELOPMENT CO., LTD

  公开号：US20170022188A1

  公开（公告）日：2017-01-26

  The invention belongs to the technical field of pharmaceutical chemistry, and particularly pertains to benzimidazole derivatives, and preparation process and pharmaceutical uses thereof. Benzimidazole derivatives include Ligustrazine and NO donor derivatives. The kind of the compounds can rapidly release Ligustrazine or No in vivo, so that they can produce effective synergetic effects with Azilsartan, to enhance the anti-hypertension effect, and reduce adverse effects, and the released Ligustrazine can produce ideal protection to patients' livers and kidneys, thereby filling blanks in the prior art

  这项发明属于药物化学技术领域，特别涉及苯并咪唑衍生物及其制备工艺和药用用途。苯并咪唑衍生物包括川芎素和NO供体衍生物。这些化合物可以在体内快速释放川芎素或NO，从而能够与阿利沙坦产生有效的协同作用，增强抗高血压效果，减少不良反应，释放的川芎素可以对患者的肝脏和肾脏产生理想的保护作用，从而填补了先前技术领域的空白。
• NO-Donor Dihydroartemisinin Derivatives as Multitarget Agents for the Treatment of Cerebral Malaria
  作者：Massimo Bertinaria、Pamela Orjuela-Sanchez、Elisabetta Marini、Stefano Guglielmo、Anthony Hofer、Yuri C. Martins、Graziela M. Zanini、John A. Frangos、Alberto Gasco、Roberta Fruttero、Leonardo J. M. Carvalho

  DOI：10.1021/acs.jmedchem.5b01036

  日期：2015.10.8

  Hybrid products in which the dihydroartemisinin scaffold is combined with NO-donor furoxan and NONOate moieties have been synthesized and studied as potential tools for the treatment of cerebral malaria (CM). The designed products were able to dilate rat aorta strips precontracted with phenylephrine with a NO-dependent mechanism. All hybrid compounds showed preserved antiplasmodial activity in vitro and in vivo against Plasmodium berghei ANKA., comparable to artesunate and artemether. Hybrid 10, selected for additional studies, was capable of increasing survival of mice with late-stage CM from 27.5% to 51.6% compared with artemether. Artemisinin-NO-donor hybrid compounds show promise as potential new drugs for treating cerebral malaria.
• Synthesis and preliminary biological profile of new NO-donor tolbutamide analogues
  作者：Yasinalli Tamboli、Loretta Lazzarato、Elisabetta Marini、Stefano Guglielmo、Michela Novelli、Pascale Beffy、Pellegrino Masiello、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/j.bmcl.2012.03.103

  日期：2012.6

  We describe a new class of NO-donor hypoglycemic products obtained by joining tolbutamide, a typical hypoglycemic sulfonylurea, with a NO-donor moiety through a hard link. As NO-donors we chose either furoxan (1,2,5-oxadiazole 2-oxide) derivatives or the classical nitrooxy function. A preliminary biological characterization of these compounds, including stimulation of insulin release from cultured rat pancreatic beta-cells and in vitro vasodilator and anti-aggregatory activities, is reported. (C) 2012 Elsevier Ltd. All rights reserved.
• Furazan and furoxan sulfonamides are strong α-carbonic anhydrase inhibitors and potential antiglaucoma agents
  作者：Konstantin Chegaev、Loretta Lazzarato、Yasinalli Tamboli、Donatella Boschi、Marco Blangetti、Andrea Scozzafava、Fabrizio Carta、Emanuela Masini、Roberta Fruttero、Claudiu T. Supuran、Alberto Gasco

  DOI：10.1016/j.bmc.2014.06.016

  日期：2014.8

  A series of furazan and furoxan sulfonamides were prepared and studied for their ability to inhibit human carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, hCA II, hCA IX, and hCA XII. The simple methyl substituted products 3-5 were potent inhibitors. Differing structural modifications of these leads had differing effects on potency and selectivity. In particular, products in which the sulfonamide group is separated from the hetero ring by a phenylene bridge retained high potency only on the hCA XII isoform. The sulfonamides 3-5 exerted intraocular pressure (IOP) lowering effects in vivo in hypertensive rabbits more efficiently than dorzolamide. Some other products (39-42), although less effective in vitro hCA II/XII inhibitors, also effectively lowered IOP in two different animal models of glaucoma. (C) 2014 Elsevier Ltd. All rights reserved.