(E)-2-(4-chlorobenzylidene)hydrazine carboxamide | 5315-86-6

• 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: (E)-2-(4-chlorobenzylidene)hydrazine carboxamide
• 英文别名: (E)-1-(4-chlorobenzylidene)semicarbazide；4-Chlorobenzaldehyde semicarbazone；[(E)-(4-chlorophenyl)methylideneamino]urea
• CAS: 5315-86-6
• 化学式: C₈H₈ClN₃O
• 分子量: 197.624
• InChiKey: RCWJOUWRVQTCSW-VZUCSPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 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：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-chlorobenzylidene)hydrazine carboxamide 在 sulfur 作用下， 生成 2,5-双(4-氯苯基)-1,3,4-噻二唑
  参考文献：
  名称：

  Solvent-Free Green Synthesis of Azines and Their Conversion to 2,5-Disubstituted-1,3,4-thiadiazoles

  摘要：

  A solvent-free, clean, and efficient method has been developed for the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles via azines. This approach exploits the synthetic potential of clean reactions and offers many advantages such as excellent product yields, easy isolation of products, and ecofriendly benign reaction conditions. The newly synthesized compounds were analyzed by infrared, H-1 NMR, C-13 NMR, and elemental analysis.

  DOI：

  10.1080/00397911.2015.1113297
• 作为产物：
  描述：

  4-氯苯甲醛 、 S-(4-叔-丁基苯甲基)[2-(1-甲基丁基)吡啶-3-基]硫代氨基甲酸酯 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 以84%的产率得到(E)-2-(4-chlorobenzylidene)hydrazine carboxamide
  参考文献：
  名称：

  Structure-Based Discovery of Thiosemicarbazone Metalloproteinase Inhibitors for Hemorrhage Treatment in Snakebites

  摘要：

  The venoms of snakes are composed by many toxins, which are responsible for various toxic effects including intense pain, bleeding disorders, and local tissue damage caused by hemorrhage and necrosis. The snake venom metalloproteinases (SVMPs) are proteolytic zinc-dependent enzymes acting in different hemostatic mechanisms. In this work, a structure-based molecular modeling strategy was used for the rational design, by means of a homology 3D model of an SVMP isolated from Bothrops pauloensis venom (BpMP-I), followed by synthesis and in vitro evaluation of new thiosemicarbazones as the first inhibitors of the B. pauloensis SVMP. Besides being effective for the SVMP inhibition, two molecules were shown to be effective also in vivo, inhibiting hemorrhage caused by the B. pauloensis whole venom. Docking studies on metalloproteinases from other snake species suggest that the thiosemicarbazones activity is not confined to BpMP-I, but seems to be a common feature of metzincins.

  DOI：

  10.1021/acsmedchemlett.7b00186

文献信息

• CARO'S ACID SUPPORTED ON SILICA GEL, PART VIII: AN EFFICIENT AND SELECTIVE REAGENT FOR CONVERSION OF PHENYLHYDRAZONES AND SEMICARBAZONES TO THE CORRESPONDING CARBONYL COMPOUNDS
  作者：Mahmood Tajbakhsh、Moslem-Mansor Lakouraj、Mohammad-Hosein Gholami、Farhad Ramzanian-Lehmali

  DOI：10.1080/10426500490466337

  日期：2004.9

  Deprotection of phenylhydrazones and semicarbazones to their parent aldehydes and ketones in high yields has been carried out using caro's acid supported on silica gel as a selective oxidant under mild conditions.

  在温和条件下，使用载在硅胶上的卡罗酸作为选择性氧化剂，将苯腙和缩氨基脲以高产率脱保护为其母体醛和酮。
• One-pot Synthesis of Stable Phosphite Ylides by three component reaction between Acetylenic Esters, Aldehyde Semicarbazones and Tributyl or Triethyl Phosphite
  作者：Mohammad Anary-Abbasinejad、Alireza Hassanabadi、Hossein Anaraki-Ardakani

  DOI：10.3184/030823407x236372

  日期：2007.8

  Three-component reaction between acetylenic esters, aldehyde semicarbazones and tributyl- or triethyl phosphite leads to stable crystalline phosphite ylides at one step in nearly quantitative yields.

  乙炔酯、醛缩氨基脲和亚磷酸三丁酯或三乙酯之间的三组分反应可一步生成稳定的结晶亚磷酸酯叶立德，收率几乎是定量的。
• Synthesis and Structural Characterization of (E)-1-(4-Chlorobenzylidene)semicarbazide
  作者：Jian Li

  DOI：10.14233/ajchem.2013.12926

  日期：——

  The compound (E)-1-(4-chlorobenzylidene)semicarbazide (C8H8N3OCl, Mr = 197.62) was synthesized and characterized by elemental analysis, IR spectra, 1H NMR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c, with a = 17.081(5), b = 4.4508(13), c = 11.896(4) Å, b = 92.979(4)º, V = 903.2(5) Å3, Z = 4, Dc = 1.453 g/cm3, l = 0.71073 Å, μ(MoKa) = 0.384 mm-1, F(000) = 408. The final refinement gave R = 0.0379, wR(F2) = 0.1000 for 1,585 observed reflections with I > 2s(I). X-ray diffraction analysis reveals that the title compound molecule adopts an E configuration about the C=N double bond. The dihedral angles between the semicarbazide group and the benzene ring is 17.4 (2)º. The crystal structure is stabilized by N–H...O hydrogen bonds.

  合成了化合物(E)-1-(4-氯亚苄基)氨基脲（C8H8N3OCl，Mr = 197.62），并通过元素分析、红外光谱、1H NMR 光谱和单晶 X 射线衍射对其进行了表征。该晶体属于单斜晶系，空间群为 P21/c，a = 17.081(5)，b = 4.4508(13)，c = 11.896(4)埃，b = 92.979(4)º, V = 903.2(5) Å3, Z = 4, Dc = 1.453 g/cm3, l = 0.71073 Å, μ(MoKa) = 0.384 mm-1, F(000) = 408。最终细化得到 R = 0.0379，wR(F2) = 0.1000，观察到 1,585 个 I > 2s(I)反射。X 射线衍射分析表明，标题化合物分子在 C=N 双键上呈 E 型构型。半咔嗪基团与苯环之间的二面角为 17.4 (2)º。晶体结构由 N-H...O 氢键稳定。
• Compounds and methods of treating infections
  申请人：Neoculi Pty Ltd.

  公开号：US10253002B2

  公开（公告）日：2019-04-09

  The invention provides compounds of Formula I, and methods of treating or preventing a bacterial infection in a subject using a compound of Formula I. The invention also provides the use of a compound of Formula I in the manufacture of a medicament for the treatment of a bacterial infection in a subject. The invention further provides a medical device when used in a method of treating or preventing a bacterial infection in a subject and to a medical device comprising the composition of the invention.

  本发明提供了式 I 化合物，以及使用式 I 化合物治疗或预防受试者细菌感染的方法。本发明还提供了式 I 化合物在制造治疗受试者细菌感染的药物中的用途。本发明进一步提供了一种用于治疗或预防受试者细菌感染方法中的医疗器械，以及包含本发明组合物的医疗器械。
• SOLIMAN F. S. G.; SHAFIK R. M.; DARWISH M., PHARMAZIE, 1979, 34, NO 3, 198-199
  作者：SOLIMAN F. S. G.、 SHAFIK R. M.、 DARWISH M.

  DOI：——

  日期：——