diazomalonaldehyde | 50704-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diazomalonaldehyde
• 英文别名: 2-Diazonio-3-oxoprop-1-en-1-olate；2-diazopropanedial
• CAS: 50704-41-1
• 化学式: C₃H₂N₂O₂
• 分子量: 98.0611
• InChiKey: JBKXCIDINOKSRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diazomalonaldehyde 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 chloromalonaldehyde
  参考文献：
  名称：

  Arnold,Z.; Sauliova,J., Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 2641 - 2647

  摘要：

  DOI：
• 作为产物：
  描述：

  2-aminopropanedialdehyde 在 溶剂黄146 、 sodium nitrite 作用下， 以2.4 g的产率得到diazomalonaldehyde
  参考文献：
  名称：

  Expeditious Synthesis of 2,3,6-Trisubstituted 2H-1,3-Oxazin-4(3H)-ones via the Tertiary Amine-Induced Reaction of 2-Diazo-3-oxoalkanals and Imines Under Mild Conditions

  摘要：

  一系列2,3,6-三取代的2H-1,3-噁嗪-4(3H)-酮衍生物通过在温和条件下，几秒钟内，利用少量三烰基胺作为催化剂，使亚胺与2-重氮-3-氧代烷醛反应，方便地合成，产率令人满意至良好。研究了不同的碱和α-重氮-β-二羰基化合物，并提出了反应机理。与相应的热引发和光引发反应相比，目前的方法是一种无金属、温和、高度区域选择性且更高效的合成2H-1,3-噁嗪-4(3H)-酮衍生物的方法。

  DOI：

  10.1055/s-0030-1258439

文献信息

• Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives
  作者：Marilia S. Costa、Núbia Boechat、Érica A. Rangel、Fernando de C. da Silva、Alessandra M.T. de Souza、Carlos R. Rodrigues、Helena C. Castro、Ivan N. Junior、Maria Cristina S. Lourenço、Solange M.S.V. Wardell、Vitor F. Ferreira

  DOI：10.1016/j.bmc.2006.08.019

  日期：2006.12

  The aim of this work was to describe the synthesis, the in vitro anti-Mycobacterium tuberculosis profile, and the structure-activity relationship (SAR) study of new N-substituted-phenyl-1,2,3-triazole-4-carbaldehydes (3a-l). The reactions of aromatic amine hydrochlorides with diazomalonaldehyde (1) produced several N-substituted-phenyl-1,2,3-triazole-4-carbaldehydes (3a-l) in moderate-to-good yields

  这项工作的目的是描述新型N-取代的苯基-1,2,3-三唑-4-甲醛的合成，体外抗结核分枝杆菌谱以及结构-活性关系（SAR）研究（ 3a-1）。芳族胺盐酸盐与重氮丙二醛（1）的反应以中等至良好的产率产生了几种N-取代的苯基-1,2,3-三唑-4-甲醛（3a-1）。为了研究二氟亚甲基对这些化合物的抗分枝杆菌活性的影响，用DAST氟化三唑可将相应的甲醛化合物以优异的产率转化为新的二氟甲基衍生物（4a-1）。所有化合物的表征均通过分光光度法进行，另外1-（4-甲基苯基）-1,2,3-三唑-4-甲醛通过X射线晶体学测定。已经针对化合物对结核分枝杆菌H37Rv菌株（ATCC 27294）的抑制活性筛选了化合物（3a-1）和（4a-1），并且它们全部都能够抑制细菌的生长。有趣的是，与目前用于治疗结核病的药物相似，3a和3k的MIC值为2.5mug / mL表现出最好的抑制作用。我们的SAR研究表明，氢键
• Stereoselective control in the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents: experimental investigation and theoretical rationalization
  作者：Hengzhen Qi、Xinyao Li、Jiaxi Xu

  DOI：10.1039/c0ob00783h

  日期：——

  The stereoselectivity of the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents was investigated experimentally by determination of the product stereochemistry and theoretically via DFT calculations. The results indicate that imines preferentially attack the less sterically hindered exo-side of the ketenes to generate zwitterionic intermediates. Subsequently, for cyclic imines, the intermediates undergo a conrotatory ring closure directly to produce β-lactams, while for linear imines, the imine moiety of the intermediates isomerizes to more stable intermediates, which further undergo a conrotatory ring closure to afford trans-β-lactams. The steric hindrance and the isomerization, rather than the torquoelectronic effect, play crucial roles in controlling the stereoselectivity in the practical Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents, although the unaccessible borylketene with a powerful electron acceptor group controls the stereoselectivity torquoelectronically, in theory.

  通过确定产物立体化学和基于密度泛函理论（DFT）的计算，实验上研究了涉及带有电子受体取代基的单取代乙烯酮的斯陶丁格反应的立体选择性。结果表明，亚胺优先攻击乙烯酮上立体障碍较小的外侧，生成内鎓离子中间体。随后，对于环状亚胺，中间体直接进行协同环合反应生成β-内酰胺；而对于线性亚胺，中间体的亚胺部分异构化为更稳定的中间体，后者进一步进行协同环合反应，产生反式β-内酰胺。在实际涉及带有电子受体取代基的单取代乙烯酮的斯陶丁格反应中，立体障碍和异构化而不是扭曲电子效应在控制立体选择性中起着关键作用，尽管在理论上，具有强电子受体基团的不可获得的硼乙烯酮通过扭曲电子效应控制立体选择性。
• Antiplatelet properties of novel N-substituted-phenyl-1,2,3-triazole-4-acylhydrazone derivatives
  作者：Anna C. Cunha、Juliana M. Figueiredo、Jorge L.M. Tributino、Ana L.P. Miranda、Helena C. Castro、Russolina B. Zingali、Carlos A.M. Fraga、Maria Cecı́lia B.V. de Souza、Vitor F. Ferreira、Eliezer J. Barreiro

  DOI：10.1016/s0968-0896(03)00055-5

  日期：2003.5

  Compounds 2b, 2d, and 2h were found to be the most potent, exhibiting a significant antiplatelet activity on arachidonic acid- and collagen-induced platelet aggregation. In addition, these new antiplatelet agents are free of gastric ulcerogenic effect and presented discrete anti-inflammatory and analgesic properties. The N-para-chlorophenyltriazolyl-4-acylhydrazone compound 2h produced the highest inhibitory

  本文描述了属于N-取代-苯基-1,2,3-三唑-4-酰基hydr类（2a-p）的新型N-酰基hydr（NAH）化合物的设计，合成和药理学评价。将经典的杂芳环生物立体异构策略应用于先前报道的N-苯基吡唑基-4-酰基hydr衍生物1，由于其对花生四烯酸诱导的血小板聚集具有重要的抗聚集特性，因此被选为铅化合物（IC（50）= 24 +/- 0.5 micro M），由此产生了这个新系列2。这些新化合物2a-p易于合成，表征和在胶原蛋白（5 micro g / mL），ADP（5 micro M）和花生四烯酸诱导的血小板聚集测定中进行测试（100 micro M）在兔子的柠檬酸盐丰富的血浆中。发现化合物2b，2d和2h最有效，对花生四烯酸和胶原蛋白诱导的血小板聚集具有显着的抗血小板活性。另外，这些新的抗血小板药没有胃溃疡作用，并具有离散的抗炎和镇痛作用。N-对氯苯基三唑基-4-酰基hydr化合物2h对胶原蛋白（IC（50）=
• AZOLE COMPOUNDS USED AS TUBERCULOSTATIC AND LEISHMANICIDE AGENTS
  申请人：Boechat Nubia

  公开号：US20090054501A1

  公开（公告）日：2009-02-26

  This invention refers to new 1,2,3-triazole and imidazole compounds included in the families of compounds represented by general formula VIII. where: X is an atom of “C” or “N;” where X is “N” the radicals do triazole ring are represented by: R 1 =COR 2 , CSR 3 , CN(R 4 )R 5 or CF 2 R 6 ; R 2 =H, NHNH 2 , alkyl, aryl substituted or not, OH, NR 7 R 8 or OR 9 ; R 3 =alkyl or aryl substituted or not; R 4 =H, OH, alkyl or aryl substituted or not; R 5 =R 6 =R 7 =R 8 =R 9 =R 10 =H, alkyl or aryl substituted or not; where X is “C” the radicals do imidazolic ring are represented by: R 1 =COR 2 ; R 2 =NHNH 2 , OH, OR 3 , or NR 4 R 5 ; R 3 =alkyl or aryl substituted or not; =R 5 H, alkyl or aryl substituted or not; R 10 =NHR 6 or NR 6 R 7 ; R 6 =R 7 =COR 8 ; R 8 =aryl substituted or not; while radical R n can be located in any one or in more than one of the carbon atoms of the aromatic ring, and these radicals can be equal or different, represented by hydrogen, alkylic groups with 1 or more carbon atoms in a linear or branched chain alkenes or alkynes, hydroxyl, hydroxyalkyl or oxygenated functions in acyclic or cyclic systems forming an heterocyclic ring, free or substituted amines, thioalkyl, donators and/or removing groupings of electrons or halogens, thus “n” can vary from 1 to 5. This invention also refers to a pharmaceutical composition comprising, as active principle, at least one of the azole compounds represented by the general formula VIII, to the use of such compositions and to method of treatment or inhibition de tuberculosis and leishmaniasis.

  本发明涉及新的1,2,3-三唑和咪唑化合物，这些化合物属于由通式VIII表示的化合物家族，其中：X是“C”或“N”的原子；当X为“N”时，三唑环的基团表示为：R1=COR2、CSR3、CN（R4）R5或CF2R6；R2=H、NHNH2、烷基、芳基取代或不取代、OH、NR7R8或OR9；R3=烷基或芳基取代或不取代；R4=H、OH、烷基或芳基取代或不取代；R5=R6=R7=R8=R9=R10=H、烷基或芳基取代或不取代；当X为“C”时，咪唑环的基团表示为：R1=COR2；R2=NHNH2、OH、OR3或NR4R5；R3=烷基或芳基取代或不取代；=R5H、烷基或芳基取代或不取代；R10=NHR6或NR6R7；R6=R7=COR8；R8=芳基取代或不取代；而基团Rn可以位于任何一个或多个芳香环的碳原子上，这些基团可以相等或不同，由氢、线性或支链烷基链上具有1个或多个碳原子的烷基基团、烯烃或炔烃、羟基、羟基烷基或在无环或环形系统中含氧杂环的功能、自由或取代的胺、硫代烷基、电子给体和/或电子受体基团或卤素表示，因此“n”可以从1到5变化。本发明还涉及一种制药组合物，其包含至少一种由通式VIII表示的唑类化合物作为活性成分，以及使用这种组合物的方法和治疗或抑制结核病和利什曼病的方法。
• Azole compounds used as tuberculostatic and leishmanicide agents
  申请人：Fundação Oswaldo Cruz—FIOCRUZ

  公开号：US08796316B2

  公开（公告）日：2014-08-05

  This invention refers to new 1,2,3-triazole and imidazole compounds included in the families of compounds represented by general formula VIII. This invention also refers to a pharmaceutical composition comprising at least one of the azole compounds represented by the general formula VIII, to the use of such compositions and to method of treatment or inhibition of tuberculosis and leishmaniasis.

  本发明涉及新的1,2,3-三唑和咪唑化合物，这些化合物包括由通式VIII所表示的化合物家族。本发明还涉及一种药物组合物，该组合物包括至少一种由通式VIII所表示的唑类化合物，以及使用这些组合物的方法和治疗或抑制结核病和利什曼病的方法。