(E)-4-chloro-N'-(4-chlorobenzylidene)benzohydrazide | 23289-03-4

• 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)-4-chloro-N'-(4-chlorobenzylidene)benzohydrazide
• 英文别名: 4-chloro-N'-(4-chlorobenzylidene)benzohydrazide；4-chloro-N-[(E)-(4-chlorophenyl)methylideneamino]benzamide
• CAS: 23289-03-4
• 化学式: C₁₄H₁₀Cl₂N₂O
• 分子量: 293.152
• InChiKey: SWHJISKQXOLDMI-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  (E)-4-chloro-N'-(4-chlorobenzylidene)benzohydrazide 在 三氯异氰尿酸 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以75%的产率得到2,5-双(4-氯苯基)-1,3,4-噁二唑
  参考文献：
  名称：

  三氯异氰尿酸介导的常温下不对称 2,5-二取代 1,3,4-恶二唑的一锅法合成

  摘要：

  摘要 使用三氯异氰脲酸 (TCCA) 在环境温度下开发了一种一锅法合成不对称 2,5-二取代 1,3,4-恶二唑的有效方法。多种芳香族和杂环醛与多种酰基肼缩合，然后氧化环化产生相应的不对称 2,5-二取代 1,3,4-恶二唑。合成的温和性质和较短的反应时间是所开发协议的显着优势。

  DOI：

  10.1080/00397910802054289
• 作为产物：
  描述：

  对氯苯甲酸甲酯 在 cobalt(II) diacetate tetrahydrate 、 potassium carbonate 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 (E)-4-chloro-N'-(4-chlorobenzylidene)benzohydrazide
  参考文献：
  名称：

  温和条件下乙酸 Co(II) 辅助酰肼直接合成酰腙

  摘要：

  以弱碱K 2 CO 3和市售Co(OAc) 2 .4H 2 O盐为催化剂，在温和条件下，实现了一种原子经济且高效的由酰肼制备多动力酰基（芳基和杂芳基）腙的方法。反应条件以甲醇为溶剂。此外，一些新型酰基腙的E/Z光开关行为已被紫外-可见光谱证实。

  DOI：

  10.1002/asia.202300755

文献信息

• A convenient CeCl3·7H2O/NaI-promoted synthesis of structurally novel and strained tricyclic β-lactams from hydrazines
  作者：Lal Dhar S. Yadav、Vijai K. Rai

  DOI：10.1016/j.tetlet.2008.07.068

  日期：2008.9

  derivatized tricyclic β-lactams has been developed. The synthesis involves CeCl3·7H2O/NaI catalyzed addition–condensation of mercaptoacetic acid and N-aroyl-N′-arylidenehydrazines followed by intramolecular cyclodehydration to afford bicyclic 5H-thiazolo[4,3-b][1,3,4]-oxadiazoles, which on treatment with acid chlorides in the presence of triethylamine furnish highly derivatized tricyclic 3H-azetidino[2

  已经开发了用于结构新颖和应变的高度衍生化的三环β-内酰胺的方便的合成方案。合成涉及加入CeCl 3 ·7H 2 O /碘化钠催化的巯基乙酸和的加成缩合Ñ -aroyl- Ñ '-arylidenehydrazines随后分子内脱水环化，得到双环5 ħ -噻唑并[4,3- b ] [1,3， 4]-恶二唑类化合物，在三乙胺存在下用酰氯处理，可提供高度衍生的三环3 H-氮杂环丁烷[2,1- b ]-噻唑并[3,4- d] [1,3,4]-恶二唑-6-酮，产率80-93％。此过程很好地说明了Ce（III）催化一锅法形成C–C，C–N和C–S键的过程。
• Modulation of estrogen-related receptors subtype selectivity: Conversion of an ERRβ/γ selective agonist to ERRα/β/γ pan agonists
  作者：Mohamed Shahien、Mohamed Elagawany、Sadichha Sitaula、Shaimaa S. Goher、Sheryl L. Burris、Ryan Sanders、Amer Avdagic、Cyrielle Billon、Lamees Hegazy、Thomas P. Burris、Bahaa Elgendy

  DOI：10.1016/j.bioorg.2020.104079

  日期：2020.9

  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.
• (Hetero-)(arylidene)arylhydrazides as Multitarget-Directed Monoamine Oxidase Inhibitors
  作者：Ashique Palakkathondi、Jong Min Oh、Sanal Dev、T. M. Rangarajan、Swafvan Kaipakasseri、Fathima Sahla Kavully、Nicola Gambacorta、Orazio Nicolotti、Hoon Kim、Bijo Mathew

  DOI：10.1021/acscombsci.0c00136

  日期：2020.11.9

  Fourteen (hetero-)(arylidene)arylhydrazide derivatives (ABH1-ABH14) were synthesized, and their inhibitory activities against monoamine oxidases (MAOs) and acetylcholinesterase (AChE) were evaluated. Compound ABHS most potently inhibited MAO-B with an IC50 value of 0.025 +/- 0.0019 mu M; ABH2 and ABH3 exhibited high IC so values as well. Most of the compounds weakly inhibited MAO-A, except ABHS (IC50 = 3.31 +/- 0.41 mu M). Among the active compounds, ABH2 showed the highest selectivity index (SI) of 174 for MAO-B, followed by ABHS (SI = 132). ABH3 and ABHS effectively inhibited AChE with IC so values of 15.7 +/- 6.52 and 16.5 +/- 7.29 mu M, respectively, whereas the other compounds were weak inhibitors of AChE. ABHS was shown to be a reversible competitive inhibitor for MAO-A and MAO-B with K-i values of 0.96 +/- 0.19 and 0.024 +/- 0.0077 mu M, respectively, suggesting that this molecule can be considered as an interesting candidate for further development as a multitarget inhibitor relating to neurodegenerative disorders.
• REDDY, P. S. N.;REDDY, P. PRATAP, INDIAN J. CHEM., 26,(1987) N 9, 890-891
  作者：REDDY, P. S. N.、REDDY, P. PRATAP

  DOI：——

  日期：——
• Trichloroisocyanuric Acid–Mediated One-Pot Synthesis of Unsymmetrical 2,5-Disubstituted 1,3,4-Oxadiazoles at Ambient Temperature
  作者：D. M. Pore、S. M. Mahadik、U. V. Desai

  DOI：10.1080/00397910802054289

  日期：2008.8.29

  method for the one-pot synthesis of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles has been developed using trichloroisocyanuric acid (TCCA) at ambient temperature. A wide variety of aromatic as well as heterocyclic aldehydes exhibit condensation with a variety of acylhydrazines followed by oxidative cyclization to yield corresponding unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles. The mild nature

  摘要 使用三氯异氰脲酸 (TCCA) 在环境温度下开发了一种一锅法合成不对称 2,5-二取代 1,3,4-恶二唑的有效方法。多种芳香族和杂环醛与多种酰基肼缩合，然后氧化环化产生相应的不对称 2,5-二取代 1,3,4-恶二唑。合成的温和性质和较短的反应时间是所开发协议的显着优势。