N-甲基吡咯醛缩氨基硫脲 | 6823-89-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-甲基吡咯醛缩氨基硫脲
• 英文名称: (E)‐2‐((1‐methyl‐1H‐pyrrol‐2‐yl)methylene)hydrazinecarbothioamide
• 英文别名: N-methylpyrrole aldehyde thiosemicarbazone；1-methyl-pyrrole-2-carbaldehyde-thiosemicarbazone；1-Methyl-pyrrol-2-carbaldehyd-thiosemicarbazon；2-[(E)-(1-methyl-1H-pyrrol-2-yl)methylidene]-1-hydrazinecarbothioamide；[(E)-(1-methylpyrrol-2-yl)methylideneamino]thiourea
• CAS: 6823-89-8
• 化学式: C₇H₁₀N₄S
• 分子量: 182.249
• InChiKey: SUSIQENTYZSKAW-WEVVVXLNSA-N

物化性质

• 沸点：
  336.9±34.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)
• 溶解度：
  20.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基吡咯醛缩氨基硫脲 、 2-溴-4'-氟苯乙酮 以 乙醇 为溶剂， 以73%的产率得到1-methylpyrrole-2-carboxaldehyde [4-(4-fluorophenyl)-1,3-thiazol-2-yl]hydrazone
  参考文献：
  名称：

  Synthesis and antimicrobial activity of some new hydrazone-bridged thiazole-pyrrole derivatives

  摘要：

  In this work, we synthesized fourteen different compounds which contain hydrazone bridged thiazole and pyrrole rings. For this purpose, pyrrole-2-carboxaldehydes were reacted directly with thiosemicarbazide in ethanol and then obtained thiosemicarbazones were condensed with alpha-bromoacetophenone derivatives (Hantzsch reaction) to give 1-substituted pyrrole-2-carboxaldehyde [4-(4-substituted phenyl)-1,3-thiazol-2-yl] hydrazones. The structures of the obtained compounds were elucidated by using IR, H-1-NMR and FAB(+)-MS spectral data and elemental analyses results. All of the compounds were screened for their antibacterial and antifungal activities against twelve different microorganisms by using microbroth dilution method. Ketoconazole and chloramphenicol were used as standard drugs. All of the compounds showed good activity against Staphylococcus aureus and Enterococcus faecalis.

  DOI：

  10.3109/14756366.2012.688043
• 作为产物：
  描述：

  N-甲基-2-吡咯甲醛 、 氨基硫脲 以 乙醇 为溶剂， 生成 N-甲基吡咯醛缩氨基硫脲
  参考文献：
  名称：

  Gold complexes with thiosemicarbazones: reactions of bi- and tridentate thiosemicarbazones with dichloro[2-(dimethylaminomethyl)phenyl-C 1,N ]gold(III), [Au(damp-C 1,N )Cl2]

  摘要：

  二氯[2-(N,N-二甲氨基甲基)苯-C1,N]金(III), [Au(damp-C1,N)Cl2] (1), 与水杨醛缩氨基硫脲(H2saltsc), 香草醛缩氨基硫脲(Hvantsc), N-甲基吡咯醛缩氨基硫脲(Hmepyrtsc), 吡哆醛缩甲基氨基硫脲(H2pydoxmetsc), 2-二苯基膦基苯甲醛缩氨基硫脲(HPtsc)或者各种取代的乙酰吡啶缩氨基硫脲(HapRtsc; R = H, Me, Ph)反应, 导致Au–N键断裂并使二甲氨基质子化. 根据通式[Au(Hdamp-C1)Cl(L)]+(L = Hsaltsc−, vantsc−, mepyrtsc−), [Au(Hdamp-C1)Cl(L)]2+(L = H2pydoxmetsc), 或者[Au(Hdamp-C1)(L)]2+(L = Ptsc−, apRtsc−, R = H, Me, Ph)分离并表征得到化合物. 为了防止金(III)中心的还原, 必须存在σ键合的2-(二甲氨基甲基)苯配体. 通过测定[Au(Hdamp-C1)Cl(Hsaltsc)](PF6) (3a), [Au(Hdamp-C1)Cl(mepyrtsc)]Cl (3c), [Au(Hdamp-C1)Cl(H2pydoxmetsc)]Cl2·MeOH (4), [Au(Hdamp-C1)(apPhtsc)]Cl2·2 MeOH (5c)和[Au(Hdamp-C1)(Ptsc)]Cl2· 1.5MeOH (6)的晶体结构, 发现金原子处于扭曲的平面四边形配位环境. 潜在的O,N,S-三齿配体H2saltsc和H2pydoxmetsc以二齿的形式配位, 没有把羟基包含在螯合骨架中, 然而HapRtsc或HPtsc以三齿的形式配位. 通常, 杂环配体的一个或者多个氢原子和/或者NMe2H+形成氢键出现在固态结构中. 对肿瘤细胞的抗增殖试验的初步结果表明这些新金配合物具有较大的细胞毒性.

  DOI：

  10.1039/a908712e

文献信息

• Gold complexes with thiosemicarbazones: reactions of bi- and tridentate thiosemicarbazones with dichloro[2-(dimethylaminomethyl)phenyl-C 1,N ]gold(III), [Au(damp-C 1,N )Cl2]
  作者：Ulrich Abram、Kirstin Ortner、Ronald Gust、Klaus Sommer

  DOI：10.1039/a908712e

  日期：——

  Dichloro[2-(N,N-dimethylaminomethyl)phenyl-C1,N]gold(III), [Au(damp-C1,N)Cl2] (1), reacts with salicylaldehyde thiosemicarbazone (H2saltsc), vanilline thiosemicarbazone (Hvantsc), N-methylpyrrole aldehyde thiosemicarbazone (Hmepyrtsc), pyridoxal methylthiosemicarbazone (H2pydoxmetsc), 2-diphenylphosphinobenzaldehyde thiosemicarbazone (HPtsc) or variously substituted acetylpyridine thiosemicarbazones (HapRtsc; R = H, Me, Ph) with cleavage of the Au–N bond and protonation of the dimethylamino group. Compounds of general formulae [Au(Hdamp-C1)Cl(L)]+ (L = Hsaltsc−, vantsc−, mepyrtsc−), [Au(Hdamp-C1)Cl(L)]2+ (L = H2pydoxmetsc) or [Au(Hdamp-C1)(L)]2+ (L = Ptsc−, apRtsc−, R = H, Me, Ph) have been isolated and characterized. The presence of the σ-bonded 2-(dimethylaminomethyl)phenyl ligand is mandatory to prevent reduction of the gold(III) centre. The crystal structures of [Au(Hdamp-C1)Cl(Hsaltsc)](PF6) (3a), [Au(Hdamp-C1)Cl(mepyrtsc)]Cl (3c), [Au(Hdamp-C1)Cl(H2pydoxmetsc)]Cl2·MeOH (4), [Au(Hdamp-C1)(apPhtsc)]Cl2·2 MeOH (5c) and [Au(Hdamp-C1)(Ptsc)]Cl2· 1.5MeOH (6) have been elucidated, showing the gold atoms in distorted square-planar co-ordination environments. The potentially O,N,S-tridentate ligands H2saltsc and H2pydoxmetsc co-ordinate in a bidentate fashion and do not incorporate the OH groups in the chelating framework, whereas HapRtsc or HPtsc co-ordinate in a tridentate manner. Generally, one or more hydrogen atoms of the heterocyclic ligands and/or the NMe2H+ group form hydrogen bridges in the solid state structures. The preliminary results of antiproliferation tests on tumor cells demonstrate the considerable cytotoxicity of these new gold complexes. p

  二氯[2-(N,N-二甲氨基甲基)苯-C1,N]金(III), [Au(damp-C1,N)Cl2] (1), 与水杨醛缩氨基硫脲(H2saltsc), 香草醛缩氨基硫脲(Hvantsc), N-甲基吡咯醛缩氨基硫脲(Hmepyrtsc), 吡哆醛缩甲基氨基硫脲(H2pydoxmetsc), 2-二苯基膦基苯甲醛缩氨基硫脲(HPtsc)或者各种取代的乙酰吡啶缩氨基硫脲(HapRtsc; R = H, Me, Ph)反应, 导致Au–N键断裂并使二甲氨基质子化. 根据通式[Au(Hdamp-C1)Cl(L)]+(L = Hsaltsc−, vantsc−, mepyrtsc−), [Au(Hdamp-C1)Cl(L)]2+(L = H2pydoxmetsc), 或者[Au(Hdamp-C1)(L)]2+(L = Ptsc−, apRtsc−, R = H, Me, Ph)分离并表征得到化合物. 为了防止金(III)中心的还原, 必须存在σ键合的2-(二甲氨基甲基)苯配体. 通过测定[Au(Hdamp-C1)Cl(Hsaltsc)](PF6) (3a), [Au(Hdamp-C1)Cl(mepyrtsc)]Cl (3c), [Au(Hdamp-C1)Cl(H2pydoxmetsc)]Cl2·MeOH (4), [Au(Hdamp-C1)(apPhtsc)]Cl2·2 MeOH (5c)和[Au(Hdamp-C1)(Ptsc)]Cl2· 1.5MeOH (6)的晶体结构, 发现金原子处于扭曲的平面四边形配位环境. 潜在的O,N,S-三齿配体H2saltsc和H2pydoxmetsc以二齿的形式配位, 没有把羟基包含在螯合骨架中, 然而HapRtsc或HPtsc以三齿的形式配位. 通常, 杂环配体的一个或者多个氢原子和/或者NMe2H+形成氢键出现在固态结构中. 对肿瘤细胞的抗增殖试验的初步结果表明这些新金配合物具有较大的细胞毒性.
• EP1399159A4
  申请人：——

  公开号：EP1399159A4

  公开（公告）日：2007-02-14
• 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：EP1399159A1

  公开（公告）日：2004-03-24
• [EN] 4-SUBSTITUTED-1-(ARYLMETHYLIDENE)THIOSEMICARBAZIDE, 4-SUBSTITUTED-1-(ARYLCARBONYL)THIOSEMICARBAZIDE AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF<br/>[FR] 4-SUBSTITUTE-1-(ARYLMETHYLIDENE)THIOSEMICARBAZIDE, 4-SUBSTITUE-1-(ARYLCARBONYL)THIOSEMICARBAZIDE ET ANALOGUES EN TANT QU'ACTIVATEURS DE CAPSASES ET DECLENCHEURS D'APOPTOSE, ET LEUR UTILISATION
  申请人：CYTOVIA INC

  公开号：WO2002098420A1

  公开（公告）日：2002-12-12

  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 o f 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.
• New Hydrazinothiazole Derivatives of Usnic Acid as Potent Tdp1 Inhibitors
  作者：Filimonov、Chepanova、Luzina、Zakharenko、Zakharova、Ilina、Dyrkheeva、Kuprushkin、Kolotaev、Khachatryan、Patel、Leung、Chand、Ayine-Tora、Reynisson、Volcho、Salakhutdinov、Lavrik

  DOI：10.3390/molecules24203711

  日期：——

  cancer therapy. Combination chemotherapy using Tdp1 inhibitors as a component can potentially improve therapeutic response to many chemotherapeutic regimes. A new set of usnic acid derivatives with hydrazonothiazole pharmacophore moieties were synthesized and evaluated as Tdp1 inhibitors. Most of these compounds were found to be potent inhibitors with IC50 values in the low nanomolar range. The activity

  酪氨酰 DNA 磷酸二酯酶 1 (Tdp1) 是癌症治疗中一个有前景的治疗靶点。使用 Tdp1 抑制剂作为成分的联合化疗可能会改善对许多化疗方案的治疗反应。合成了一组新的具有 hydrazonothiazole 药效团部分的松萝酸衍生物，并作为 Tdp1 抑制剂进行了评估。大多数这些化合物被发现是有效的抑制剂，IC50 值在低纳摩尔范围内。化合物的活性通过结合实验得到验证，并得到分子模型的支持。还证明了以无毒浓度使用的最有效抑制剂使肿瘤对抗癌药物拓扑替康敏感的能力。研究了抑制剂和拓扑替康对其协同作用的给药顺序，