2-pyridinecarbaldehyde 2'-thienyl hydrazone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-pyridinecarbaldehyde 2'-thienyl hydrazone
• 英文别名: 2-pyridylcarboxaldehyde 2-thiophenecarbonyl hydrazone；(E)-N'-(pyridin-2-ylmethylene)thiophene-2-carbohydrazide；(E)-N’-(pyridin-2-ylmethylene)thiophene-2-carbohydrazone；2-pyridylketone-2-thiophenecarboxaldehyde hydrazone；2-pyridylcarboxaldehyde 2-thiophenecarboxyl hydrazone；N-[(E)-2-pyridylmethyleneamino]thiophene-2-carboxamide；N-[(E)-pyridin-2-ylmethylideneamino]thiophene-2-carboxamide
• 化学式: C₁₁H₉N₃OS
• 分子量: 231.278
• InChiKey: OVTBJOBSMVRHJS-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-pyridinecarbaldehyde 2'-thienyl hydrazone 以 乙腈 为溶剂， 反应 0.17h， 以82%的产率得到(Z)-N'-(pyridin-2-ylmethylene)thiophene-2-carbohydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519
• 作为产物：
  描述：

  噻吩-2-羧酸甲酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 2-pyridinecarbaldehyde 2'-thienyl hydrazone
  参考文献：
  名称：

  含噻吩核的N-酰基hydr：一种新的抗癌药

  摘要：

  在这项研究中，我们提出了一系列含有噻吩核作为新的抗癌类的N-酰基hydr。评价了该系列中的57种化合物对四种人类癌细胞系的活性。细胞毒性（IC 50）范围为0.82至12.90μM。化合物（E）-N '-（2-羟基-3-甲氧 基亚苄基）噻吩-2-碳酰肼在所有细胞系中均表现出良好的细胞毒活性（IC 50 = 0.82-5.36μM），并在该系列中获得最佳结果；因此，它是这一新类中的重要铅化合物。

  DOI：

  10.1007/s00044-017-1832-y

文献信息

• Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole##This paper represents contribution # 36 of the LASSBio, UFRJ (Br.) (LASSBio, http://acd.ufrj.br/≈pharma/lassbio); For contribution # 35, see [24].
  作者：Patrícia C. Lima、Lídia M. Lima、Kelli Cristine M. da Silva、Paulo Henrique O. Léda、Ana Luisa P. de Miranda、Carlos A.M. Fraga、Eliezer J. Barreiro

  DOI：10.1016/s0223-5234(00)00120-3

  日期：2000.2

  Anew series of antinociceptive compounds belonging to the N-acylarylhydrazone (NAH) class were synthesized from natural safrole (7). The most analgesic derivative represented by 10f, [(4'-N,N-dimethylaminobenzylidene-3-(3', 4'-methylenedioxyphenyl)propionylhydrazine], was more potent than dipyrone and indomethacin, used as standards. The NAH compounds described herein were structurally planned by molecular

  从天然黄樟脑合成了一系列新的N-酰基芳基hydr（NAH）类抗伤害感受化合物（7）。以10f表示的最止痛衍生物，[（4'-N，N-二甲基氨基苄叉基-3-（3'，4'-亚甲基二氧苯基）丙酰肼]]比双嘧啶和消炎痛更有效，用作标准品。我们通过分子杂交和经典生物立体异构策略对先前报道的止痛NAH进行结构规划，以鉴定N-酰基芳基hydr部分的药效学作用并研究这些系列中的构效关系（SAR）。
• N-acylhydrazones containing thiophene nucleus: a new anticancer class
  作者：Laura N. F. Cardoso、Thais C. M. Nogueira、Felipe A. R. Rodrigues、Augusto Cesar Aragão Oliveira、Maria Claudia dos Santos Luciano、Claudia Pessoa、Marcus V. N. de Souza

  DOI：10.1007/s00044-017-1832-y

  日期：2017.8

  In this study, we present a series of N-acylhydrazones containing thiophene nuclei as a new anticancer class. Fifty-seven compounds in this series were evaluated for their activity against four human cancer cell lines. Cytotoxicity (IC50) ranged from 0.82 to 12.90 μM. The compound (E)-N′-(2-hydroxy-3-methoxybenzylidene)thiophene-2-carbohydrazide displayed good cytotoxic activity in all cell lines (IC50 = 0

  在这项研究中，我们提出了一系列含有噻吩核作为新的抗癌类的N-酰基hydr。评价了该系列中的57种化合物对四种人类癌细胞系的活性。细胞毒性（IC 50）范围为0.82至12.90μM。化合物（E）-N '-（2-羟基-3-甲氧 基亚苄基）噻吩-2-碳酰肼在所有细胞系中均表现出良好的细胞毒活性（IC 50 = 0.82-5.36μM），并在该系列中获得最佳结果；因此，它是这一新类中的重要铅化合物。
• [EN] TREATMENT OF ISCHEMIC EYE DISEASE BY THE SYSTEMATIC PHARMACEUTICAL ACTIVATION OF HYPOXIA INDUCIBLE FACTOR (HIF)<br/>[FR] TRAITEMENT D'UNE MALADIE ISCHÉMIQUE DE L'OEL PAR ACTIVATION PHARMACEUTIQUE SYSTÉMATIQUE D'UN FACTEUR INDUIT PAR L'HYPOXIE (HIF)
  申请人：CLEVELAND CLINIC FOUNDATION

  公开号：WO2009035534A2

  公开（公告）日：2009-03-19

  The present invention consists of a method of treating a subject with an ischemic eye disease associated with the down-regulation of HIF comprising administering to the subject an effective amount of a compound that induces HIF activity and/or induces EPO activity to induce and maintain growth or normal retinal blood vessels in the early stage of the disease.
• N-acylhydrazones confer inhibitory efficacy against New Delhi metallo-β-lactamase-1
  作者：Han Gao、Jia-Qi Li、Peng-Wei Kang、Jia-Zhu Chigan、Huan Wang、Lu Liu、Yin-Sui Xu、Le Zhai、Ke-Wu Yang

  DOI：10.1016/j.bioorg.2021.105138

  日期：2021.9
• Acylhydrazones as Widely Tunable Photoswitches
  作者：Derk Jan van Dijken、Petr Kovaříček、Svante P. Ihrig、Stefan Hecht

  DOI：10.1021/jacs.5b09519

  日期：2015.12.2

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.