4-<(4-chlorobenzoyl)oxy>benzaldehyde | 108577-34-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-<(4-chlorobenzoyl)oxy>benzaldehyde
• 英文别名: 4-chlorobenzoic acid 4-formylphenyl ester；4-(4-chlorobenzoyloxy)benzaldehyde；4-formylphenyl 4-chlorobenzoate；4-Chlor-benzoesaeure-(4-formyl-phenylester)；(4-formylphenyl) 4-chlorobenzoate
• CAS: 108577-34-0
• 化学式: C₁₄H₉ClO₃
• mdl: MFCD00579080
• 分子量: 260.677
• InChiKey: KQSDBATZVOQQQY-UHFFFAOYSA-N

物化性质

• 熔点：
  119.2-119.7 °C
• 沸点：
  420.6±30.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-<(4-chlorobenzoyl)oxy>benzaldehyde 在 sodium tetrahydroborate 作用下， 以64%的产率得到4‐(hydroxymethyl)phenyl 4‐chlorobenzoate
  参考文献：
  名称：

  作为选择性 ALDH1A3 抑制剂的苄氧基苯甲醛衍生物的设计、合成、生物学评价和计算机模拟研究

  摘要：

  醛脱氢酶 1A3 (ALDH1A3) 最近受到癌症领域研究人员的关注。几项研究报告了 ALDH1A3 在不同癌症类型中的过度表达，已发现这与治疗恢复不佳有关。因此，寻找针对 ALDH1A3 的选择性抑制剂可能会为癌症治疗带来新的治疗选择。在本研究中，基于生理底物相似性设计了 ALDH1A3 选择性候选物，使用 ALDH 阳性 A549 和 ALDH 阴性 H1299 细胞合成和研究了 ALDH1A1、ALDH1A3 和 ALDH3A1 的选择性和细胞毒性。发现具有苄氧基苯甲醛支架的两种化合物（ABMM-15 和 ABMM-16）是最有效和选择性的 ALDH1A3 抑制剂，IC 50值分别为 0.23 和 1.29 µM。结果还显示 ABMM-15 和 ABMM-16 对任一细胞系都没有显着的细胞毒性。然而，与 A549 细胞相比，一些其他候选物（ABMM-6、ABMM-24、ABMM-32）对

  DOI：

  10.3390/molecules26195770
• 作为产物：
  描述：

  对氯苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 生成 4-<(4-chlorobenzoyl)oxy>benzaldehyde
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Rhodanine Derivatives as Aldose Reductase Inhibitors

  摘要：

  Aldose reductase (ALR) enzyme plays a significant role in conversion of excess amount of glucose into sorbitol in diabetic condition, inhibitors of which decrease the secondary complication of diabetes mellitus. To understand the structural interaction of inhibitors with ALR enzyme and develop more effective ALR inhibitors, a series of substituted 5‐phenylbenzoate containing N‐substituted rhodanine derivatives were synthesized and evaluated for their in vitro ALR inhibitory activity. Docking studies of these compounds were carried out, which revealed that the 5‐phenylbenzoate moiety deeply influenced the key π‐π stacking while 4‐oxo‐2‐thioxothiazolidines contributed in hydrogen bond interactions. The phenyl ring of benzylidene system occupied in specific pocket constituted from Phe115, Phe122, Leu300 and Cys303 while the rhodanine ring forms a tight net of hydrogen bond with Val47 at anionic binding site of the enzyme. The structural insights obtained from the docking study gave better understanding of rhodanine and macromolecular interaction and will help us in further designing and improving of ALR inhibitory activity of rhodanine analogs.

  DOI：

  10.1111/cbdd.12369

文献信息

• (Aryloxy)aryl Semicarbazones and Related Compounds:  A Novel Class of Anticonvulsant Agents Possessing High Activity in the Maximal Electroshock Screen
  作者：Jonathan R. Dimmock、Ramanan N. Puthucode、Jennifer M. Smith、Mark Hetherington、J. Wilson Quail、Uma Pugazhenthi、Terry Lechler、James P. Stables

  DOI：10.1021/jm9603025

  日期：1996.1.1

  A number of (aryloxy)aryl semicarbazones and related compounds were synthesized and evaluated for anticonvulsant activities. After intraperitoneal injection to mice, the semicarbazones were examined in the maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ), and neurotoxicity (NT) screens. The results indicated that greater protection was obtained in the MES test than the scPTZ screen

  合成了许多（芳氧基）芳基半咔唑酮和相关化合物，并评估了其抗惊厥活性。腹膜内注射给小鼠后，在最大电击（MES），皮下戊四氮（scPTZ）和神经毒性（NT）筛查中检查了氨基脲。结果表明，MES测试比scPTZ屏幕获得了更大的保护。对大约三分之一的化合物进行定量后，发现平均保护指数（PI，即TD50 / ED50）约为9。口服给予大鼠后，许多化合物在MES筛查中表现出显着的效力（1-5 mg的ED50） / kg），同时具有很高的保护指数。实际上，一半以上的化合物的PI值均大于100，而其中两种化合物的PI值均超过300。口服给予大鼠后，该化合物在scPTZ和NT筛选中基本无活性。与三种参考临床使用药物相比，各种化合物在小鼠腹膜内和大鼠口服筛查中显示出更高的效价和PI值。产生的数据支持结合位点假说。定量的构效关系表明了许多物理化学参数，这些参数有助于MES筛查中的活性。五个化合物的X射线晶体学分
• Imidazo[2,1-b]thiazepines: synthesis, structure and evaluation of benzodiazepine receptor binding
  作者：Katarzyna Kieć-Kononowicz、Janina Karolak-Wojciechowska、Barbara Michalak、Elżbieta Pękala、Britta Schumacher、Christa E Müller

  DOI：10.1016/j.ejmech.2003.11.009

  日期：2004.3

  of our search for new ligands acting on benzodiazepine receptors among the fused 2-thiohydantoin derivatives, a series of 5-substituted imidazo[2,1-b]thiazepines was synthesized and investigated in radioligand binding studies at the benzodiazepine binding site of GABA(A) receptors in rat brain cortical membranes. Among ortho-substituted 5-arylidene-imidazo[2,1-b]thiazepines compounds could be identified

  为了继续研究在稠合的2-硫代乙内酰脲衍生物中作用于苯并二氮杂receptor受体的新配体，合成了一系列5取代的咪唑并[2,1-b]硫氮杂s，并在放射性配体结合研究中对苯并二氮杂binding的结合位点进行了研究。大鼠脑皮质膜中的GABA（A）受体。在邻位取代的5-亚芳基-咪唑并[2，1-b]噻嗪类化合物中，可以鉴定出在低微摩尔浓度下对苯并二氮杂卓结合位点具有亲和力的化合物。已经对两种化合物（6ae和6ag）进行了X射线结构分析。为了分析构效关系，已经完成了所有化合物的3D模型（使用X射线数据）。检查了计算的理化性质（log P和log D）以及实验薄层色谱数据。
• Effects of Branching of the Ester Alkyl Chain on the Mesomorphic Properties of Alkyl 4-[4-(4-Substituted benzoyloxy)benzylideneamino]benzoates
  作者：Hiroyuki Matsuzaki、Yoshio Matsunaga

  DOI：10.1246/bcsj.63.2300

  日期：1990.8

  The mesomorphic properties of five homologous series of alkyl 4-[4-(4-X-substituted benzoyloxy)benzylideneamino]benzoates, where X=CN,NO2, CH3, Cl, and CH3COO, have been studied. The ester alkyl groups employed were the following eleven types: ethyl and propyl and their mono-, di-, and trimethyl-substituted ones. Although the introduction of the first branching methyl group to the ester alkyl chain depresses the nematic stability, the second and/or third groups may either further depress or enhance the stability, depending upon the nature of the substituent X. While all of the members of the cyano and nitro derivatives are purely nematogenic, many members of the other three series display a smectic A phase, as well as a nematic phase. In addition to the above-mentioned esters, the butyl, pentyl, and their monomethyl-substituted esters were examined in order to demonstrate that the effects on the thermal stability of the smectic A phase of the branching of the ester alkyl chain and those of the substituent X are also interdependent.

  五个同系物系列的烷基4-[4-(4-X取代苯甲氧基)苯亚胺]苯甲酸酯的介质相性质进行了研究，其中X=CN，NO2，CH3，Cl和CH3COO。所采用的酯烷基有以下十一种类型：乙基、丙基及其单、双、三甲基取代物。尽管向酯烷基链引入第一个分枝甲基会降低向列相的稳定性，但第二个和/或第三个取代基可能会进一步降低或增强稳定性，这取决于取代基X的性质。虽然所有的氰基和硝基衍生物都是纯粹的向列液晶，但其他三类中的许多成员显示出层状A相，以及向列相。除了上述酯类之外，还检查了丁基、戊基及其单甲基取代的酯，以证明酯烷基链的分枝及取代基X对层状A相热稳定性的影响也是相互依存的。
• Effects of Polysubstitution on Mesomorphic Properties: Chloro and Methyl Derivatives of<i>N</i>-[4-(4-Substituted benzoyloxy)benzylidene]anilines
  作者：Hiroyuki Hasegawa、Tatsuya Masuda、Yoshio Matsunaga、Sachiko Seo、Kazuaki Yasuhara

  DOI：10.1246/bcsj.62.2875

  日期：1989.9

  The effects of mono-, di-, and trichloro substitution of the aniline moiety on the nematic-isotropic transition temperature of N-[4-(4-X-substituted benzoyloxy)benzylidene]anilines, where X=CH3O, CH3, or Cl, have been studied, while paying particular attention to the vicinal chlorines. While the substituent on the 2 or 3 position of the aniline moiety lowers the transition temperature of the parent

  苯胺部分的单、二和三氯取代对 N-[4-(4-X-取代的苯甲酰氧基)苄叉]苯胺的向列各向同性转变温度的影响，其中 X=CH3O、CH3 或 Cl , 已被研究，同时特别注意邻氯。虽然苯胺部分 2 或 3 位上的取代基降低了母体化合物和 4-氯衍生物的转变温度，但 2,3-二氯衍生物显示出高于 2- 或 3-氯衍生物的温度衍生物。此外，2,3,4-三氯衍生物的转变温度高于3,4-二氯衍生物的转变温度，略低于2,4-二氯异构体的转变温度。相反，无论其他取代基的位置如何，4-取代基的引入都会增加温度。
• Chemical Modification of Coumarin Dimer and HIV-1 Integrase Inhibitory Activity.
  作者：Pili Chih-Min Mao、Jean-Francois Mouscadet、Herve Leh、Christian Auclair、Ling-Yih Hsu

  DOI：10.1248/cpb.50.1634

  日期：——

  A systematic series of chemically modified coumarin dimmers has been synthesized and tested for their inhibitory activity against HIV-1 integrase. We observed that modified coumarin dimmers containing hydrophobic moiety on the linker display potent inhibitory activities.

  我们合成了一系列经过化学修饰的香豆素二聚体，并测试了它们对 HIV-1 整合酶的抑制活性。我们发现，在连接体上含有疏水分子的修饰香豆素二聚体具有很强的抑制活性。