pyridine-2-formaldehyde N⁴-ethyl thiosemicarbazone | 98954-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: pyridine-2-formaldehyde N⁴-ethyl thiosemicarbazone
• 英文别名: 2-formylpyridine-4N-ethyl-thiosemicarbazone；Hydrazinecarbothioamide, N-ethyl-2-(2-pyridinylmethylene)-；1-ethyl-3-(pyridin-2-ylmethylideneamino)thiourea
• CAS: 98954-07-5
• 化学式: C₉H₁₂N₄S
• 分子量: 208.287
• InChiKey: BSARYNMULKHEMH-UHFFFAOYSA-N

物化性质

• 熔点：
  215-217 °C(Solv: methanol (67-56-1))
• 沸点：
  334.6±34.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  potassium tetrachloropalladate(II) 、 pyridine-2-formaldehyde N⁴-ethyl thiosemicarbazone 以 甲醇 为溶剂， 以50%的产率得到[palladium(II)(2-formylpyridine-4Nethyl-thiosemicarbazone)2]
  参考文献：
  名称：

  Synthesis, structure, spectroscopic studies and cytotoxic effect of novel palladium(II) complexes with 2-formylpyridine-4-Nethyl-thiosemicarbazone: Potential antitumour agents

  摘要：

  New palladium(II) complexes have been synthesized by the reaction of Pd(II) with 2-formylpyridine-4-Nethyl-thiosemicarbazone, HFo4NEt, 1. The complexes [Pd(Fo4NEt)Cl], 2, [Pd(H(2)Fo4NEt)(Fo4NEt)Cl-2], 3 and [Pd(Fo4NEt)(2)], 4 have been characterised by elemental analyses and spectroscopic studies. The crystal structure of the complex [Pd(H(2)Fo4NEt)(Fo4NEt)Cl-2], 3 and the protonated ligand [(H(2)Fo4NEt)Cl], 5 have been solved by single-crystal X-ray diffraction. The cytotoxic activities of 1-4 have been evaluated for antiproliferative activity in vitro against the cells of three human cancer cell lines: MCF-7 (human breast cancer cell line), T24 (bladder cancer cell line), A-549 (non-small cell lung carcinoma) and a mouse L-929 (a fibroblast-like cell line cloned from strain L). The compound 3 display IC50 values in a mu M range better than that of the antitumor drug cis-platin against MCF-7 and T-24 cell lines and is considered as agent with potential antitumor activity candidates for further stages of screening in vitro and/or in vivo. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.06.068
• 作为产物：
  描述：

  吡啶-2-甲醛 、 4-乙基-3-硫代氨基脲 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以76%的产率得到pyridine-2-formaldehyde N⁴-ethyl thiosemicarbazone
  参考文献：
  名称：

  合成，结构，抗微生物活性和吡啶-2-甲醛生物安全评估Ñ -susbtituted-thiosemicarbazonates铜（II）†

  摘要：

  吡啶-2-甲醛-N 1-取代的硫代半氨基甲酮{（C 5 H 4 N 4）HC 2 N 3 -N 2（H）–C 1（S）N 1 HR}（缩写HL 1 -R：R = Me，Et，Ph）与乙腈-二氯甲烷混合物（1：1，v / v）中的卤化铜（I）生成了一系列具有中心配位核心的Cu II络合物：[Cu II X（N， N，SL 1 -R）]（R = Me，Et，Ph：X = I，1-3 ; Br，4-6，Cl，7-9），借助分析数据，红外，紫外可见和ESR光谱，ESI质谱和单晶X射线晶体学对其进行了表征。硫配体通过吡啶基氮-N 4，偶氮甲碱氮-N 3和硫醇基硫与阴离子的阴离子（L 1 -R）-配位于Cu II，并且Cu II进一步键合至碘化物，溴化物或氯化物。为了探索其生物活性，配合物（1-9），以及先前报道的Cu II的2- benzoylpyridine-络合物ñ -取代的缩氨基硫脲{（C 5

  DOI：

  10.1039/c8nj03619e

文献信息

• The influence of substituents at C2/N1 atoms of pyridine-2-formaldeyhde-/benzaldehyde-N1-substituted thiosemicarbazones on the type of copper(I) complexes
  作者：Rekha Sharma、Tarlok S. Lobana、Alfonso Castineiras、Ray J. Butcher、Takashiro Akitsu

  DOI：10.1016/j.poly.2018.11.034

  日期：2019.1

  coordinating through sulfur only. Copper(I) halides with benzaldehyde-N1-substituted thiosemicarbazones (C6H5)HC2 N3-N2(H)-C1( S)-N1HR; R = Me, Et; HL2-Me; HL2-Et} and Ph3P have yielded halogen bridged dinuclear complexes, [Cu2(μ-X)2(κS1-HL2-R)2(Ph3P)2] (X, R: I, Me, 6; Br, Me, 7; I, Et, 8; Br, Et, 9; Cl, Et, 10). For R = phenyl at N1 atom, copper(I) halides with two m moles of HL2-Ph have formed sulfur–bridged

  摘要碘化亚铜（I）与PPh3在乙腈中形成经验组成的化合物CuI（Ph3P）}等摩尔反应，并在氯仿中与吡啶-2-甲醛-N-甲基硫代半碳氮（C5H4N）HC2 N3-N2进一步反应-（H）-C1（S）N1HR; R =我；HL1-Me}从同一反应容器中分离出[CuICl（Ph3P）（κS1-H2L1-Me）1a，四聚体[Cu4I4（Ph3P）4] 1b和游离HL1-Me 1c的晶体。 1a涉及从氯仿中提取氯，并具有吡啶-N质子化的硫配体，溴化铜/氯化物与Ph3P和HL1-Me或HL1-Et也形成吡啶基质子化[CuBr2（Ph3P）（κS1-H2L1- Me）] 2，[CuCl2（Ph3P）（κS1-H2L1-Me）] 3，[CuBr2（Ph3P）（κS1-H2L1-Et）] 4和[CuCl2（Ph3P）（κS1-H2L1-Et）] 5。在这些反应中也鉴定出类似于1b和1c的产物。在这四个
• 4-substituted-1- (arylmethylidene) thiosemicarbazide, 4-substituted-1- (arylcarbonyl) thiosemicarbazide and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：——

  公开号：US20030045581A1

  公开（公告）日：2003-03-06

  The present invention is directed to optionally substituted 4-substituted-1-(arylmethylidene)thiosemicarbazide, 4-substituted-1-(arylcarbonyl)thiosemicarbazide and analogs thereof, represented by the Formulae I and II: 1 wherein A 1 , A 2 , Q and R 1 -R 3 are defined herein. The present invention also relates to the discovery that compounds having Formulae I and II are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及可选取代的4-取代-1-(芳基甲基亚胺基)硫脲、4-取代-1-(芳基羰基)硫脲及其类似物，其化学式如下：式中A1、A2、Q和R1-R3如定义所述。本发明还涉及发现化合物I和II具有激活半胱氨酸蛋白酶和诱导细胞凋亡的作用。因此，本发明的半胱氨酸蛋白酶激活剂和细胞凋亡诱导剂可用于诱导在各种临床情况下出现的异常细胞的不受控制的生长和扩散的细胞死亡。
• 4-substituted-1-(arylmethylidene)thiosemicarbazide, 4-substituted-1-(arylcarbonyl)thiosemicarbazide and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cytovia, Inc.

  公开号：US06794400B2

  公开（公告）日：2004-09-21

  The present invention is directed to optionally substituted 4-substituted-1-(arylmethylidene)thiosemicarbazide, 4-substituted-1-(arylcarbonyl)thiosemicarbazide and analogs thereof, represented by the Formulae I and II: wherein A1, A2, Q and R1-R3 are defined herein. The present invention also relates to the discovery that compounds having Formulae I and II are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及可选取代的4-取代-1-(芳基甲基亚硫基)脲、4-取代-1-(芳基羰基)亚硫基脲及其类似物，其化学式分别为I和II：其中A1、A2、Q和R1-R3在此定义。本发明还涉及发现具有化学式I和II的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于在各种临床情况下诱导细胞死亡，其中出现了异常细胞的不受控制的生长和扩散。
• Synthesis, structures, antimicrobial activity and biosafety evaluation of pyridine-2-formaldehyde-<i>N</i>-susbtituted-thiosemicarbazonates of copper(<scp>ii</scp>)
  作者：Mani Kaushal、Tarlok S. Lobana、Lovedeep Nim、Jaskamal Kaur、Ritu Bala、Geeta Hundal、Daljit S. Arora、Isabel Garcia-Santos、Courtney E. Duff、Jerry P. Jasinski

  DOI：10.1039/c8nj03619e

  日期：——

  e mixture (1 : 1, v/v) have yielded a novel series of CuII complexes with a central coordination core: [CuIIX(N,N,S-L1-R)] (R = Me, Et, Ph: X = I, 1–3; Br, 4–6, Cl, 7–9), which have been characterized with the help of analytical data, IR, UV-visible and ESR spectroscopy, ESI-mass spectrometry and single crystal X-ray crystallography. The thio-ligands coordinate to CuII as anions (L1-R)− through pyridyl

  吡啶-2-甲醛-N 1-取代的硫代半氨基甲酮（C 5 H 4 N 4）HC 2 N 3 -N 2（H）–C 1（S）N 1 HR}（缩写HL 1 -R：R = Me，Et，Ph）与乙腈-二氯甲烷混合物（1：1，v / v）中的卤化铜（I）生成了一系列具有中心配位核心的Cu II络合物：[Cu II X（N， N，SL 1 -R）]（R = Me，Et，Ph：X = I，1-3 ; Br，4-6，Cl，7-9），借助分析数据，红外，紫外可见和ESR光谱，ESI质谱和单晶X射线晶体学对其进行了表征。硫配体通过吡啶基氮-N 4，偶氮甲碱氮-N 3和硫醇基硫与阴离子的阴离子（L 1 -R）-配位于Cu II，并且Cu II进一步键合至碘化物，溴化物或氯化物。为了探索其生物活性，配合物（1-9），以及先前报道的Cu II的2- benzoylpyridine-络合物ñ -取代的缩氨基硫脲（C 5
• Synthesis, structure, spectroscopic studies and cytotoxic effect of novel palladium(II) complexes with 2-formylpyridine-4-Nethyl-thiosemicarbazone: Potential antitumour agents
  作者：Dimitra Kovala-Demertzi、Anastasia Galani、John R. Miller、Christopher S. Frampton、Mavroudis A. Demertzis

  DOI：10.1016/j.poly.2012.06.068

  日期：2013.3

  New palladium(II) complexes have been synthesized by the reaction of Pd(II) with 2-formylpyridine-4-Nethyl-thiosemicarbazone, HFo4NEt, 1. The complexes [Pd(Fo4NEt)Cl], 2, [Pd(H(2)Fo4NEt)(Fo4NEt)Cl-2], 3 and [Pd(Fo4NEt)(2)], 4 have been characterised by elemental analyses and spectroscopic studies. The crystal structure of the complex [Pd(H(2)Fo4NEt)(Fo4NEt)Cl-2], 3 and the protonated ligand [(H(2)Fo4NEt)Cl], 5 have been solved by single-crystal X-ray diffraction. The cytotoxic activities of 1-4 have been evaluated for antiproliferative activity in vitro against the cells of three human cancer cell lines: MCF-7 (human breast cancer cell line), T24 (bladder cancer cell line), A-549 (non-small cell lung carcinoma) and a mouse L-929 (a fibroblast-like cell line cloned from strain L). The compound 3 display IC50 values in a mu M range better than that of the antitumor drug cis-platin against MCF-7 and T-24 cell lines and is considered as agent with potential antitumor activity candidates for further stages of screening in vitro and/or in vivo. (C) 2012 Elsevier Ltd. All rights reserved.