(E)-N’-(thiophen-2-ylmethylene)isonicotinohydrazide | 79728-82-8

• 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: (E)-N’-(thiophen-2-ylmethylene)isonicotinohydrazide
• 英文别名: (E)-N'-(thiophen-2-ylmethylene)-isonicotinohydrazide；N-[(E)-thiophen-2-ylmethylideneamino]pyridine-4-carboxamide
• CAS: 79728-82-8
• 化学式: C₁₁H₉N₃OS
• mdl: MFCD00453589
• 分子量: 231.278
• InChiKey: VQHKTXKJAYPSHY-MDWZMJQESA-N

物化性质

• 熔点：
  226 °C(Solv: ethanol (64-17-5))
• 密度：
  1.29±0.1 g/cm3(Predicted)

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：

  (E)-N’-(thiophen-2-ylmethylene)isonicotinohydrazide 以 乙腈 为溶剂， 反应 0.17h， 生成 (Z)-N'-(thiophen-2-ylmethylene)isonicotinic hydrazide
  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：

  (Z)-N'-(thiophen-2-ylmethylene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 0.75h， 生成 (E)-N’-(thiophen-2-ylmethylene)isonicotinohydrazide
  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

文献信息

• Anti-infective compounds
  申请人：Brodin Priscille

  公开号：US20110178077A1

  公开（公告）日：2011-07-21

  The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.

  本发明涉及小分子化合物及其在治疗细菌感染，特别是结核病方面的用途。
• Synthesis, Inhibition of Mycobacterium tuberculosis Enoyl-acyl Carrier Protein Reductase and Antimycobacterial Activity of Novel Pentacyanoferrate(II)-isonicotinoylhydrazones
  作者：Thais Gazzi、Mariane Rotta、Anne Villela、Valnês Rodrigues-Junior、Leonardo Martinelli、Francisco Sales、Eduardo de Sousa、Maria Campos、Luiz Basso、Diógenes Santos、Pablo Machado

  DOI：10.21577/0103-5053.20170033

  日期：——

  Mycobacterium tuberculosis 2-trans-enoyl-ACP(CoA) reductase (MtInhA) in a time-dependent manner. The most active coordination complex showed an increase of more than ten-fold in the MtInhA inhibition rate constant compared with lead pentacyano(isoniazid)ferrate(II) (IQG607). Additionally, the new series of metal-based compounds demonstrated antitubercular activity against a drug-susceptible Mycobacterium tuberculosis

  结核病仍然是由单一病原体引发的主要死亡原因之一。在本文中，描述了使用超声能量的更绿色的异烟酰酰肼合成方法。这些化合物被用作合成戊酸高铁（II）异烟酰酰肼的起始原料，它以时间依赖性的方式抑制了结核分枝杆菌2-反式-烯酰-ACP（CoA）还原酶（MtInhA）催化的反应。最活跃的配位复合物显示出MtInhA抑制率常数比五氰基铅（异烟肼）高铁酸盐（II）（IQG607）增长十倍以上。此外，新的基于金属的化合物系列还显示了对药物敏感的结核分枝杆菌（Mtb）菌株的抗结核活性，并且对哺乳动物细胞没有毒性（IC50> 20μmolL，最大抑制浓度的一半）。最后，一种合成的化合物在Mtb感染的巨噬细胞模型中显示出与异烟肼相似的细胞内活性，表明该化学类别可能提供新的结构，从而开始抗结核药物开发的临床前阶段。
• Small molecule efflux pump inhibitors
  申请人：UNIVERSITY OF ROCHESTER

  公开号：US10471028B2

  公开（公告）日：2019-11-12

  Small molecule efflux pump inhibitors are provided, as well as methods for their use in treating infections. Also provided herein are methods of using the small molecule efflux pump inhibitors to restore the antibiotic susceptibility of microbes.

  本文提供了小分子外排泵抑制剂及其用于治疗感染的方法。本文还提供了使用小分子外排泵抑制剂恢复微生物抗生素敏感性的方法。
• An Isoniazid Based Schiff Base Sensor for Selective Detection of Pd2+ Ions
  作者：Jasbir Singh、Shubham Saini、Ravish K. Chauhan、Pallavi Bhardwaj、Ashwani Kumar、Virender .

  DOI：10.1007/s10895-023-03491-x

  日期：——

  developed a novel isoniazid based fluorescent probe (E)-N’-(thiophen-2-ylmethylene)isonicotinohydrazide (TINH) through simple condensation reaction and employed for selective detection of Pd2+ ions with a low detection limit of 4.102 × 10–11 M. Among the many existing cations, TINH bound Pd2+ ions with an association affinity of 9.794 × 105 M−1. Adding Pd2+ ions to ligand solution increased the absorption

  在这里，我们通过简单的缩合反应开发了一种基于异烟肼的新型荧光探针(E)-N'-(噻吩-2-基亚甲基)异烟酰肼( TINH )，并用于选择性检测Pd 2+离子，检测限低至4.102 × 10 –11  M。在许多现有的阳离子中，TINH与 Pd 2+离子结合，缔合亲和力为 9.794 × 10 5  M -1。在配体溶液中添加 Pd 2+离子增加了紫外-可见光的吸收强度，并淬灭了荧光光谱实验中的发射强度。更重要的是，这种TINH以 1:1 的化学计量比与 Pd 2+离子络合。为了评估复杂系统的稳定性，进行了pH实验。配体和Pd 2+离子之间的结合见解已通过红外光谱和质谱方法得到证实。此外，TINH还应用于实际水样中Pd 2+离子的识别和测量。因此，该系统非常适用于低检测范围内环境和工业样品中Pd 2+离子的检测。 图形概要
• Sah; Peoples, Journal of the American Pharmaceutical Association (1912), 1954, vol. 43, p. 513,514
  作者：Sah、Peoples

  DOI：——

  日期：——