3-hydrazino-3-oxo-N-(2-thiazolyl)propanamide | 18612-28-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-hydrazino-3-oxo-N-(2-thiazolyl)propanamide
• 英文别名: 3-hydrazinyl-oxo-N-(1,3-thiazole-2-yl)-propanamide；3-hydrazino-3-oxo-N-thiazol-2-yl-propanamide；3-(2-thiazolylamino)-3-oxopropanehydrazide；Malonsaeure-monohydrazid-thiazolyl-(2)-amid；3-hydrazinyl-3-oxo-N-(thiazol-2-yl)propanamide；N-thiazol-2-yl-malonamic acid hydrazide；2-hydrazinocarbonyl-N-thiazol-2-yl-acetamide；3-hydrazinyl-3-oxo-N-(1,3-thiazol-2-yl)propanamide
• CAS: 18612-28-7
• 化学式: C₆H₈N₄O₂S
• 分子量: 200.221
• InChiKey: RYTXVTGXANVUCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydrazino-3-oxo-N-(2-thiazolyl)propanamide 在 cobalt salt 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 [Co2(3-(2-(4-methoxyphenylcarbamothioyl)hydrazinyl)-3-oxo-N-(thiazol-2-yl)propanamide)2](NO₃)₂*H₂O
  参考文献：
  名称：

  Synthesis, Characterization, and Antiproliferative Activity of Cu²⁺, V(IV)O²⁺, Co²⁺, Mn²⁺, and Ni²⁺Complexes with 3-(2-(4-Methoxyphenylcarbamothioyl)Hydrazinyl)-3-OXO-N-(Thiazol-2-yl)Propanamide against Human Breast Adenocarcinoma Cells

  摘要：

  3-(2-(4-methoxyphenylcarbamothioyl)hydrazinyl)-3-oxo-N-(thiazol-2-yl)propanamide (H4L) has been synthesized and its structure has been confirmed by elemental analysis, IR, mass, and H-1 and C-13 NMR spectroscopy. This ligand has been used to synthesize complexes with Cu2+, V(IV)O2+, Co2+, Mn2+, and Ni2+. The structures of these complexes have been verified by elemental analyses, molar conductivities, magnetic measurements as well as UV-VIS, IR, H-1-NMR spectroscopy. The IR spectra showed that H4L acts as a uni-negative tetradentate or bidentate ligand. The molar conductance measurements proved that all complexes are nonelectrolytes except complexes 2 and 3. Moreover, the metal complexes geometrical arrangements were square planar, tetrahedral, square-pyramidal, or octahedral. The structures are consistent with the IR, UV-VIS, ESR, as well as conductivity measurements. The antiproliferative activity of the synthesized complexes against human breast adenocarcinoma MCF-7 cell line showed exploited potent to moderate growth inhibitory activity, in particular complex 4 which exhibited superior potency to the reference drug cisplatin. The antitumor activity of these compounds was accompanied by significant increase in the activity of superoxide dismutase with concomitant decrease in the activities of catalase and glutathione peroxidase and reduced glutathione level. The overproduction of free radicals allowed reactive oxygen species-mediated tumor cells death.

  DOI：

  10.1080/10426507.2013.855764
• 作为产物：
  描述：

  methyl 2-(thiazol-2-ylcarbamoyl)acetate 在 肼 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以86%的产率得到3-hydrazino-3-oxo-N-(2-thiazolyl)propanamide
  参考文献：
  名称：

  2-（噻唑-2-基氨基甲酰基）乙酸甲酯合成新型噻唑啉衍生物的合成，抗心律失常和抗凝活性

  摘要：

  一系列新颖的噻唑并衍生物2 - 17由2-（噻唑-2-基氨基甲酰基）乙酸酯的初始缩合合成1用不同的有机试剂异硫氰酸苯酯和进一步的反应。通过IR，1 H NMR，EIMS光谱数据和元素分析确认了新合成的化合物的结构。最初，化合物的急性毒性是通过确定其LD 50来测定的。筛选所有化合物的抗心律不齐和抗凝活性，与普鲁卡因酰胺和利多卡因作为阳性对照相比，它们显示出较高的抗心律不齐活性。详细的合成，光谱数据，LD 50 并报道了合成化合物的药理活性。

  DOI：

  10.1016/j.ejmech.2008.05.004

文献信息

• 1,8-Naphthyridines VI. Synthesis and anti-inflammatory activity of 5-(alkylamino)-N,N-diethyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides with a new substitution pattern on the triazole ring
  作者：Mario Di Braccio、Giancarlo Grossi、Giorgio Roma、Daniela Piras、Francesca Mattioli、Marzia Gosmar

  DOI：10.1016/j.ejmech.2007.04.016

  日期：2008.3

  in which the 9-alkyl substituent was replaced by an ester or amide group (compounds 3a-i), was prepared and tested (inhibition of carrageenan-induced paw edema in the rat). Also two 5-(N-alkyl,N-acylamino) derivatives (compounds 4a,b) were synthesized and evaluated for the same purpose. Even though the general trend for these new [1,2,4]triazolo[4,3-a][1,8]naphthyridine derivatives was a decrease

  基于9-烷基-N，N-二烷基-5-（烷基氨基）[1,2,4]三唑并[4,3-a] [1,8]萘啶-显示的良好的抗炎特性。制备并测试了6碳基乙酰胺1的一系列类似物，其中9-烷基取代基被酯或酰胺基取代（化合物3a-i）（抑制角叉菜胶诱发的爪水肿）。鼠）。还合成了两种5-（N-烷基，N-酰基氨基）衍生物（化合物4a，b），并出于相同目的对其进行了评估。尽管这些新的[1,2,4]三唑并[4,3-a] [1,8]萘啶衍生物的总体趋势是与化合物1相比活性降低，但一些新合成的化合物仍显示出良好的抗-发炎的特性。
• Physicochemical studies and biological evaluation on (E)-3-(2-(1-(2-hydroxyphenyl)hydrazinyl)-3-oxo-N-(thiazol-2yl)propanamide complexes
  作者：K.M. Ibrahim、R.R. Zaky、E.A. Gomaa、M.N. Abd El-Hady

  DOI：10.1016/j.saa.2013.01.031

  日期：2013.4

  the different decomposition steps of some complexes have been calculated using the Coats–Redfern equation. Also, the association and formation constants of Co(II) ion in absolute ethanol solutions at 294.15 K have been calculated by using electrical conductance. Moreover, the ligand and its complexes have been screened for their antibacterial (Escherichia coli and Clostridium sp.) and antifungal activities

  Co（II），Ni（II），Cu（II），Pd（II），Cd（II），Zn（II）和U（VI）O 2与（E）-3-（2-（合成了1-（2-羟基苯基）肼基）-3-氧代-N-（噻唑-2-基）丙酰胺（H 2 o -HAH），并通过分析（元素和热），光谱学（1） 1 H NMR，13C NMR，IR，可见紫外线，ESR，MS）和物理测量值（磁化率和摩尔电导）。使用Coats–Redfern方程计算了某些配合物不同分解步骤的动力学和热力学参数。而且，已经通过使用电导率计算了在无水乙醇溶液中294.15 K时Co（II）离子的缔合和形成常数。此外，已经通过MIC方法筛选了配体及其配合物的抗菌（大肠埃希氏菌和梭状芽孢杆菌）和抗真菌活性（曲霉和茎杆菌）。
• Spectral, magnetic, thermal, molecular modelling, ESR studies and antimicrobial activity of (E)-3-(2-(2-hydroxybenzylidene) hydrazinyl)-3-oxo-n(thiazole-2-yl)propanamide complexes
  作者：R.R. Zaky、T.A. Yousef

  DOI：10.1016/j.molstruc.2011.06.050

  日期：2011.9

  (E)-3-(2-(2-hydroxybenzylidene)hydrazinyl)-3-oxo-n(thiazole-2-yl) propane-mide (H2L) has been prepared and its structure confirmed by elemental analysis, IR and (HNMR)-H-1 spectroscopy. It has been used to produce diverse complexes with Ni(II), Co(II) and Cu(II) ions. The complexes obtained have been investigated by thermal analysis, spectral studies (IR, UV-visible. ESR). and magnetic measurements. IR spectra suggest that the H2L acts as a bidentate ligand coordinating via (C=N)(1), and (OH)(phenolic) or deprotonated enolized carbonyl oxygen (=C-O-)(1). The electronic spectra of the complexes and their magnetic moments provide information about geometries. The room temperature solid state ESR spectra of the Cu(II) complexes show d(x2-y2) as a ground state, suggesting tetragonally distorted octahedral or square-planar geometries around Cu(II) centre. The molar conductance measurements proved that the complexes are non-electrolytes. The bond length, bond angle, HOMO, LUMO, dipole moment and charges on the atoms have been calculated to confirm the geometry of the ligand and the investigated complexes. Also, thermal properties and decomposition kinetics of all compounds are investigated. The interpretation, mathematical analysis and evaluation of kinetic parameters (Ea, A, Delta H, Delta S and Delta G) of all thermal decomposition stages have been evaluated using Coats-Redfern and Horowitz-Metzger methods. Finally, the antimicrobial activity has been tested. (C) 2011 Elsevier B.V. All rights reserved.

  (E)-3-(2-(2-hydroxybenzylidene)hydrazinyl)-3-oxo-n(thiazole-2-yl) 磷酸甲硫 зав (H2L) 已被制备并经元素分析、红外光光谱 (IR) 和 (HNMR)-H-1 光谱确认了其结构。该配体已经被用于与 Ni(II)、Co(II) 和 Cu(II) 铁离子生成多样的配合物。所得到的配合物被通过热分析、光谱研究 (IR、UV-Vis、ESR) 和磁测量进行了考察。红外光谱认为 H2L 作为二dentate 载体，通过 (C=N)(1) 和 (OH)(酚羟基) 或去质子化羰基氧 (=C-O)(1) 坐标。配合物的电子光谱和它们的磁矩提供了几何学的信息。Cu(II) 坐标中心的室温固态 ESR �光谱表明基态为 d(x2-y2)，表明 Cu(II) 周围四角形扭曲八面体或四方形平面几何。摩尔导电率测定证明这些配合物是是非电离体。配体中键长、键角、HOMO、LUMO、偶矩和原子电荷等被计算，以确认配合物中配体的几何结构。另外，研究了所有化合物的热性质和分解动力学特性。配合物的所有分解步骤的热动力学参数 (Ea、A、ΔH、ΔS 和 ΔG) 被通过对 Coats-Redfern 和 Horowitz-Metzger 方法的数学分析和评价。最后，抗微生物活性测试进行了番笕。
• Practical and computational studies on novel Schiff base complexes derived from green synthesis approach: Conductometry as well as in-vitro screening supported by in-silico study
  作者：Reem Shah、Hanadi Katouah、Anas A. Sedayo、Matokah Abualnaja、Meshari M. Aljohani、Fawaz Saad、Rania Zaky、Nashwa M. El-Metwaly

  DOI：10.1016/j.molliq.2020.114116

  日期：2020.12

  A new Schiff base ligand was prepared and characterized then used to synthesize new metal ion complexes using ball milling technique. These complexes were elucidated by analytical, spectral and conformational tools, to establish their formulae. Mononuclear complexes (1M:1L) were proposed through neutral or mononegative mode within bidentate or tridentate binding. Octahedral configuration was proposed

  制备了新的席夫碱配体并进行了表征，然后使用球磨技术将其用于合成新的金属离子配合物。通过分析，光谱和构象工具阐明了这些配合物，以建立其配方。在中齿或三齿结合中，通过中性或单负性模式提出了单核复合物（1M：1L）。除了Pd（II）络合物具有方平面几何形状以外，所有络合物均建议使用八面体构型。使用EDX，SEM和XRD了解元素百分比，形貌特征以及结晶度。动力学和热力学参数通过两种已知方法估算。在存在或不存在配体的情况下，对Cu（II）和Ni（II）离子进行电导滴定，以获得缔合常数和形成常数。根据Hirshfeld方法，使用Crystal Explorer软件为晶体包装系统建立3-D模型。对于对氧原子有高贡献的配体模型，观察到强分子接触。对微生物，自由基和结直肠癌细胞系（HCT-116）进行了生物筛选。配体有时甚至超过了参考药物，显然具有优异的抑制活性。应用MOE，以最高得分姿势针对不同病原体蛋白
• Potential anticancer agents. I. Synthesis of some nitrogen mustard containing benzylidenehydrazides
  作者：M. G. Dhapalapur、S. S. Sabnis、C. V. Deliwala

  DOI：10.1021/jm00307a037

  日期：1968.1