4-((4-chlorobenzyl)oxy)benzohydrazide | 136563-59-2

• 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: 4-((4-chlorobenzyl)oxy)benzohydrazide
• 英文别名: 4-(4-Chloro-benzyloxy)-benzoic acid hydrazide；4-[(4-Chlorophenyl)methoxy]benzohydrazide
• CAS: 136563-59-2
• 化学式: C₁₄H₁₃ClN₂O₂
• 分子量: 276.722
• InChiKey: FATOOLUXJUJUHM-UHFFFAOYSA-N

物化性质

• 熔点：
  162-163 °C
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((4-chlorobenzyl)oxy)benzohydrazide 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-{4'-(4''-chlorobenzyloxy)-phenyl}-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole-6(5H)-thione
  参考文献：
  名称：

  Rastogi, Nisheeth; Kant, Padam; Sethi, Rakesh, Journal of the Indian Chemical Society, 2012, vol. 89, # 9, p. 1235 - 1240

  摘要：

  DOI：
• 作为产物：
  描述：

  过氧化氢酶 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 9.5h， 生成 4-((4-chlorobenzyl)oxy)benzohydrazide
  参考文献：
  名称：

  Synthesis and Anticonvulsant Activity Evaluation of 4-butyl-5-(4- alkoxyphenyl)-2H-1,2,4-triazole-3(4H)-ones

  摘要：

  设计并合成了一系列4-丁基-5-(4-烷氧基苯基)-2H-1,2,4-三唑-3(4H)-酮(6a-6u)，并通过最大电击试验和旋转体试验评估了这些化合物的抗惊厥作用和神经毒性。在合成的化合物中，4-丁基-5-(4-(2-氟苄基)苯基)-2H-1,2,4-三唑-3 (4H)-酮（6k）的药效最强，ED50 值为 27.4 mg/kg，保护指数（PI = TD50/ED50）值为 12.0。除了抗 MES 的药效外，化合物 6k 对戊烯四唑（PTZ）、3-巯基丙酸（3-MP）和双谷氨酸（BIC）诱导的癫痫发作也有很强的抑制作用，这表明其抗惊厥活性可能涉及包括增强 GABA 能活性在内的作用机制。

  DOI：

  10.2174/1570180810666131122003939

文献信息

• Derivatives of 4-(hetero)arylmethyloxy phenyl diazole, a method of
  申请人：Delalande S.A.

  公开号：US05262432A1

  公开（公告）日：1993-11-16

  Derivatives having the formula: ##STR1## in which R.sub.1 =C.sub.1 -C.sub.4 alkyl and Ar is an aryl or heteroaryl group chosen from among the following: (i) ##STR2## where R.sub.2 represents a hydrogen atom one or two halogen atoms, a CN, NO.sub.2 or CF.sub.3 group, one, two or three C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups or an amino group substituted by two C.sub.1 -C.sub.4 alkyl groups, in which case the --W--V-- chain represent ##STR3## and n=2-6; (ii) pyridyl, in which case the --W--V-- chain represents --N.dbd.N--and n=1-6, and acid addition salts of those derivatives (I) which are salt-forming. These derivatives are of use in therapy as agents for inhibiting type B monoamine oxydase.

  具有以下式子的衍生物：##STR1## 其中 R.sub.1 = C.sub.1 -C.sub.4 烷基，Ar是从以下选择的芳基或杂环芳基：(i) ##STR2## 其中R.sub.2代表氢原子，一个或两个卤素原子，CN，NO.sub.2或CF.sub.3基团，一个，两个或三个C.sub.1 -C.sub.4烷基或C.sub.1 -C.sub.4烷氧基或由两个C.sub.1 -C.sub.4烷基取代的氨基基团，在这种情况下，--W--V--链代表##STR3## 并且n=2-6; (ii) 吡啶基，在这种情况下，--W--V--链代表--N.dbd.N--且n=1-6，以及那些是盐形成的衍生物(I)的酸加成盐。这些衍生物在治疗中用作抑制B型单胺氧化酶的药物。
• Development of Receptor for Advanced Glycation End Products (RAGE) ligands through target directed dynamic combinatorial chemistry: a novel class of possible antagonists
  作者：Anca‐Elena Dascalu、Christophe Furman、Isabelle Landrieu、François‐Xavier Cantrelle、Justine Mortelecque、Gaëlle Grolaux、Philippe Gillery、Frédéric Tessier、Emmanuelle Lipka、Muriel Billamboz、Eric Boulanger、Alina Ghinet

  DOI：10.1002/chem.202303255

  日期：2024.4.5

  Tackling the Receptor for Advanced Glycation End Products (RAGE) inhibition via Dynamic Combinatorial Chemistry (DCC). Leveraging protein recognition, in the presence of a continually self-correcting, evolving dynamic library, we were able to find novel ligands for RAGE. Our biological tests confirmed their superior affinities, as well as potential as antagonists, a fresh perspective for inhibiting

  通过动态组合化学 (DCC) 解决高级糖基化终产物 (RAGE) 受体抑制问题。利用蛋白质识别，在不断自我修正、不断进化的动态库的存在下，我们能够找到 RAGE 的新型配体。我们的生物测试证实了它们卓越的亲和力以及作为拮抗剂的潜力，为抑制这种多方面的炎症相关受体提供了新的视角。
• Harrison, Darwin Anil; Rastogi, Nisheeth; Rahman, Masihur, Indian Journal of Heterocyclic Chemistry, 2014, vol. 23, # 4, p. 411 - 418
  作者：Harrison, Darwin Anil、Rastogi, Nisheeth、Rahman, Masihur

  DOI：——

  日期：——
• 5-[4-(Benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives and related analogs: new reversible, highly potent, and selective monoamine oxidase type B inhibitors
  作者：Fathi Mazouz、Salah Gueddari、Claude Burstein、Daniel Mansuy、Rene Milcent

  DOI：10.1021/jm00061a006

  日期：1993.4

  Thirty-three new 5-[4-(benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives including related analogues, designed as inhibitors of monoamine oxidase type B (MAO B), were synthesized and investigated both in vitro and ex vivo for their abilities to inhibit selectively rat brain MAO B over MAO A. Three inhibitors were found to act as reversible, highly potent, and selective MAO B inhibitors, namely the nitrile derivative 5-[4-(benzyloxy)phenyl]-3-(2-cyanoethyl)-1,3,4-oxadiazol-2(3H)-one (12a) and two closely related homologues, the corresponding oxadiazolethione 13a and the alcohol 14b. Their IC50(MAO B) values are in the low nanomolar range of 1.4-4.6 nM and their selectivities, estimated by the ratio of IC50 values (A/B), are from 3200 to >71 400. Compound 12a exhibited the highest activity against MAO B. Its IC50 was evaluated to be 1.4 nM with a quasitotal selectivity (>71 400) toward this enzyme. In ex vivo studies, 12a showed a reversible and short duration of action. MAO B was markedly inhibited with the oral dose of 1 mg/kg without any alteration of MAO A, and the inhibition almost did not exceed 24 h. Its ED50 (1 h after oral administration) was evaluated to be 0.56 mg (1.7 mumol)/kg. Remarkably, MAO A was not affected at doses as high as 1500 mg/kg, po. In addition, no apparent toxicity or behavioral anomaly was observed during the treatment even at the maximum administrated dose. SAR studies emphasize the existence of three binding sites to the enzyme with a special importance of the terminal phenyl. Analysis of the inhibition kinetics indicated that 12a acts in a two-step mechanism as a competitive, slow, and tight-binding inhibitor of MAO B with a K(i) value of 0.22 muM and an overall K(i)* value at equilibrium of 0.7 nM.
• Rastogi, Nisheeth; Harrison, Darwin Anil; Tripathi, Diwakar, Journal of the Indian Chemical Society, 2009, vol. 86, # 9, p. 991 - 995
  作者：Rastogi, Nisheeth、Harrison, Darwin Anil、Tripathi, Diwakar、Shukla, Sarveshwar

  DOI：——

  日期：——