(E)-2-chloro-N'-(2-hydroxybenzylidene)benzohydrazide | 82859-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-chloro-N'-(2-hydroxybenzylidene)benzohydrazide
• 英文别名: (E)-salicylaldehyde 2-chlorobenzoyl；H2LASSBio-466；2-chloro-benzoic acid salicylidenehydrazide；2-Chlor-benzoesaeure-salicylidenhydrazid；2-chloro-N-[(E)-(2-hydroxyphenyl)methyleneamino]benzamide；2-chloro-N-[(E)-(2-hydroxyphenyl)methylideneamino]benzamide
• CAS: 82859-77-6
• 化学式: C₁₄H₁₁ClN₂O₂
• 分子量: 274.707
• InChiKey: UUWKFQZODPGLRA-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 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：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-chloro-N'-(2-hydroxybenzylidene)benzohydrazide 、 巯基乙酸 以 苯 为溶剂， 反应 10.0h， 以85%的产率得到2-Chloro-N-[2-(2-hydroxy-phenyl)-4-oxo-thiazolidin-3-yl]-benzamide
  参考文献：
  名称：

  Dutta; Goswami; Kataky, Journal of the Indian Chemical Society, 1990, vol. 67, # 4, p. 332 - 334

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯苯甲酸甲酯 在 一水合肼 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (E)-2-chloro-N'-(2-hydroxybenzylidene)benzohydrazide
  参考文献：
  名称：

  Modulation of estrogen-related receptors subtype selectivity: Conversion of an ERRβ/γ selective agonist to ERRα/β/γ pan agonists

  摘要：

  Estrogen Related Receptors (ERRs) are key regulators of energy homeostasis and play important role in the etiology of metabolic disorders, skeletal muscle related disorders, and neurodegenerative diseases. Among the three ERR isoforms, ERR alpha emerged as a potential drug target for metabolic and neurodegenerative diseases. Although ERR beta/gamma selective agonist chemical tools have been identified, there are no chemical tools that effectively target ERR alpha agonism. We successfully engineered high affinity ERR alpha agonism into a chemical scaffold that displays selective ERR beta/gamma agonist activity (GSK4716), providing novel ERR alpha/beta/gamma pan agonists that can be used as tools to probe the physiological roles of these nuclear receptors. We identified the structural requirements to enhance selectivity toward ERR alpha. Molecular modeling shows that our novel modulators have favorable binding modes in the LBP of ERR alpha and can induce conformational changes where Phe328 that originally occupies the pocket is dislocated to accommodate the ligands in a rather small cavity. The best agonists up-regulated the expression of target genes PGC-1 alpha and PGC-1 beta, which are necessary to achieve maximal mitochondrial biogenesis. Moreover, they increased the mRNA levels of PDK4, which play an important role in energy homeostasis.

  DOI：

  10.1016/j.bioorg.2020.104079

文献信息

• Analgesic and Anti-Inflammatory Activities of Salicylaldehyde 2-Chlorobenzoyl Hydrazone (H2LASSBio-466), Salicylaldehyde 4-Chlorobenzoyl Hydrazone (H2LASSBio-1064) and Their Zinc(II) Complexes
  作者：Walfrido Bispo Júnior、Magna S. Alexandre-Moreira、Marina A. Alves、Anayive Perez-Rebolledo、Gabrieli L. Parrilha、Eduardo E. Castellano、Oscar E. Piro、Eliezer J. Barreiro、Lídia Moreira Lima、Heloisa Beraldo

  DOI：10.3390/molecules16086902

  日期：——

  Salicylaldehyde 2-chlorobenzoyl hydrazone (H2LASSBio-466), salicylaldehyde 4-chlorobenzoyl hydrazone (H2LASSBio-1064) and their complexes [Zn(LASSBio-466)H2O]2 (1) and [Zn(HLASSBio-1064)Cl]2 (2) were evaluated in animal models of peripheral and central nociception, and acute inflammation. All studied compounds significantly inhibited acetic acid-induced writhing response. Upon coordination the anti-nociceptive activity was favored in the complex 1. H2LASSBio-466 inhibited only the first phase of the formalin test, while 1 was active in the second phase, like indomethacin, indicating its ability to inhibit nociception associated with the inflammatory response. Hence coordination to zinc(II) altered the pharmacological profile of H2LASSBio-466. H2LASSBio-1064 inhibited both phases but this effect was not improved by coordination. The studied compounds did not increase the latency of response in the hot plate model, indicating their lack of central anti-nociceptive activity. All compounds showed levels of inhibition of zymosan-induced peritonitis comparable or superior to indomethacin, indicating an expressive anti-inflammatory profile.

  水杨醛2-氯苯甲腇（H2LASSBio-466）、水杨醛4-氯苯甲腇（H2LASSBio-1064）及其配合物[Zn(LASSBio-466)H2O]2（1）和[Zn(HLASSBio-1064)Cl]2（2）在外周和中枢痛觉反应及急性炎症的动物模型中进行了评估。所有研究的化合物均显著抑制了醋酸诱导的扭体反应。在配位后，复合物1的抗痛觉活性得到了增强。H2LASSBio-466仅抑制了形式的测试中的第一阶段，而1在第二阶段中表现活跃，如吲哚美辛，表明其能够抑制与炎症反应相关的痛觉。因此，配位锌（II）改变了H2LASSBio-466的药理特征。H2LASSBio-1064抑制了两个阶段，但这种效果在配位后并没有改善。研究的化合物未增加热板模型中的反应潜伏期，表明其缺乏中枢抗痛觉活性。所有化合物对酵母菌诱导的腹膜炎的抑制水平与吲哚美辛相当或更高，表明其具有显著的抗炎特性。
• Sah, Recueil des Travaux Chimiques des Pays-Bas, 1940, vol. 59, p. 1029,1034
  作者：Sah

  DOI：——

  日期：——
• Sun; Sah, Science Reports of National Tsing Hua University, Series A: Mathematical, Physical, and Engineering Sciences, 1934, vol. <A> 2, p. 359,361
  作者：Sun、Sah

  DOI：——

  日期：——
• Poddar, S. N.; Samanta, G. C.; Mukherjee, G., Journal of the Indian Chemical Society, 1985, vol. 62, # 1, p. 7 - 10
  作者：Poddar, S. N.、Samanta, G. C.、Mukherjee, G.、Ghosh, S.

  DOI：——

  日期：——
• DUTTA, M. M.;GOSWAMI, B. N.;KATAKY, J. C. S., J. INDIAN CHEM. SOC., 67,(1990) N, C. 332-334
  作者：DUTTA, M. M.、GOSWAMI, B. N.、KATAKY, J. C. S.

  DOI：——

  日期：——