1H-咪唑-4,5-二甲酰氯 | 59399-36-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1H-咪唑-4,5-二甲酰氯
• 英文名称: 4,5-bis(chloroformyl)imidazole
• 英文别名: imidazole-4,5-dicarboxylic acid chloride；Imidazol-4,5-dicarbonsaeure-dichlorid；1H-imidazole-4,5-dicarbonyl dichloride；4,5-imidazolediformyl chloride；1H-Imidazole-4,5-dicarbonyl dichloride；1H-imidazole-4,5-dicarbonyl chloride
• CAS: 59399-36-9
• 化学式: C₅H₂Cl₂N₂O₂
• 分子量: 192.989
• InChiKey: FKFGGOYAMHRBBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  1H-咪唑-4,5-二甲酰氯 、 苯酚 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 diphenyl 5,10-dioxo-5H,10H-diimidazo[1,5-a:1',5'-d]pyrazine-1,6-dicarboxylate
  参考文献：
  名称：

  Discovery of a novel 5-carbonyl-1H-imidazole-4-carboxamide class of inhibitors of the HIV-1 integrase–LEDGF/p75 interaction

  摘要：

  Though much progress has been made in the inhibition of HIV-1 integrase catalysis, clinical resistance mutations have limited the promise of long-term drug prescription. Consequently, allosteric inhibition of integrase activity has emerged as a promising approach to antiretroviral discovery and development. Specifically, inhibitors of the interaction between HIV-1 integrase and cellular cofactor LEDGF/p75 have been validated to diminish proviral integration in cells and deliver a potent reduction in viral replicative capacity. Here, we have contributed to the development of novel allosteric integrase inhibitors with a high-throughput AlphaScreen-based random screening approach, with which we have identified novel 5-carbonyl-1H-imidazole-4-carboxamides capable of inhibiting the HIV-1 integrase-LEDGF/p75 interaction in vitro. Following a structure-activity relationship analysis of the initial 1H-imidazole-4,5-dicarbonyl core, we optimized the compound's structure through an industrial database search, and we went further to synthesize a selective and non-cytotoxic panel of inhibitors with enhanced potency. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.047
• 作为产物：
  描述：

  咪唑-4,5-二羧酸 在 氯化亚砜 作用下， 反应 24.0h， 生成 1H-咪唑-4,5-二甲酰氯
  参考文献：
  名称：

  环扩增（“脂肪”）核苷和核苷酸类似物对黄病毒NTPase / Helase（包括西尼罗河病毒，丙型肝炎病毒和日本脑炎病毒）表现出强大的体外活性。

  摘要：

  一系列含有咪唑并[4,5-e] [1,3]二氮杂ring环系统的环膨胀（“脂肪”）杂环，核苷和核苷酸类似物（REN）（9、14、15、18、24-26 ，28、31和33）和咪唑并[4,5-e] [1,2,4]三氮杂ring环系统（30b，30c，32和34）已被合成为黄病毒科NTPase /螺旋酶的潜在抑制剂包括西尼罗河病毒（WNV），丙型肝炎病毒（HCV）和日本脑炎病毒（JEV）。该研究还包括人酶Suv3（delta1-159）的氨基末端截短形式，以评估RENs对病毒酶的选择性。REN的类似物包括杂环碱基第1位的结构变异，并且在两种糖部分的类型（核糖，2'-脱氧核糖，和无环糖）以及这些糖与杂环碱基的连接方式（α与β端基异构构型）。针对病毒NTPase / helase的解旋酶和ATPase活性分别进行生化筛选目标REN。许多REN抑制病毒解旋酶活性，其IC50值在微摩尔浓度范围内变化，

  DOI：

  10.1021/jm030842j

文献信息

• Models for Visual Pigments. The Effect of the Imidazolyl Group on the Absorption Maxima of the Retinal Schiff Base
  作者：Masato Nanasawa、Hiroyoshi Kamogawa

  DOI：10.1246/bcsj.54.1101

  日期：1981.4

  protonated with imidazole derivatives under neutral conditions and was absorbed at longer wavelengths compared with carboxylic acids. The absorption peak with the imidazolyl group intramolecularly combined was highly affected by the structure, protonated Nα-retinylidene-L-histidine octadecylamide having an absorption maximum at 494 nm caused by the inductive effect and the polar imidazolyl group.

  使用外部添加或分子内组合的咪唑基研究了标题效应。N-视黄基丁胺在中性条件下被咪唑衍生物质子化，并且与羧酸相比在更长的波长下被吸收。分子内结合咪唑基的吸收峰受结构的影响很大，质子化的 Nα-视黄亚基-L-组氨酸十八烷基酰胺在 494 nm 处具有最大吸收，由诱导效应和极性咪唑基引起。
• The synthesis, characterization and catalytic application of manganese porphyrins bonded to novel modified SBA-15
  作者：Saeed Rayati、Parinaz Nafarieh、Mostafa M. Amini

  DOI：10.1039/c8nj00743h

  日期：——

  SBA-TMSIm was used as a support for the coordinative anchoring of tetraphenylporphyrinato-manganese(III) acetate [Mn(TPP)OAc] via axial ligation. The prepared catalyst was characterized using different spectroscopic methods and the amount of loaded metalloporphyrin on SBA-TMSIm was determined via atomic absorption spectroscopy. Finally, the immobilized metalloporphyrin was found to be an efficient catalyst

  在本研究中，使用咪唑作为功能化试剂（SBA-TMSIm）对高度有序的介孔二氧化硅材料（SBA-15）进行了功能化，然后通过FT-IR光谱，热重分析（TGA），粉末X射线衍射（ XRD）和氮吸附/解吸等温线。SBA-TMSIm通过轴向连接被用作四苯基卟啉-乙酸锰（III）乙酸盐[Mn（TPP）OAc]的配位锚定的支持物。使用不同的光谱学方法和加载金属卟啉上SBA-TMSIm量测定所制备的催化剂进行了表征通过原子吸收光谱法。最后，发现固定化的金属卟啉是一种以分子氧和异丁醛（IBA）为助氧化剂氧化苯乙烯的有效催化剂。此外，该好氧氧化系统用于氧化各种烯烃，结果表明它们的环氧化物是主要产物。
• Ring expanded nucleosides and nucleotides
  申请人：——

  公开号：US20040077564A1

  公开（公告）日：2004-04-22

  The present invention relates to compositions comprising analogues of purine nucleosides containing a ring-expanded (“fat”) heterocyclic ring, in place of purine, and an unmodified or modified sugar residue, pharmaceutically acceptable derivatives of such compositions, as well as methods of use thereof. In particular, these compositions may be utilized in the treatment of certain cancers, bacterial, fungal, parasitic, and viral infections, including, but not limited to, Acquired Immunodeficiency Syndrome (AIDS), hepatitis, Epstein-Barr and cytomegalovirus.

  本发明涉及含有环扩张（“肥胖”）杂环环代替嘌呤的嘌呤核苷类似物和未经改性或改性的糖残基的组合物，以及这些组合物的药学上可接受的衍生物，以及其使用方法。特别地，这些组合物可用于治疗某些癌症、细菌、真菌、寄生虫和病毒感染，包括但不限于获得性免疫缺陷综合症（AIDS）、肝炎、EB病毒和巨细胞病毒。
• Ring-expanded nucleosides and nucleotides
  申请人：Nabi

  公开号：EP1227103B1

  公开（公告）日：2006-07-26
• RING-EXPANDED NUCLEOSIDES AND NUCLEOTIDES
  申请人：Burns, Barry

  公开号：EP0724587A1

  公开（公告）日：1996-08-07