iso-phthalic acid monobenzyl ester | 113266-88-9

• 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: iso-phthalic acid monobenzyl ester
• 英文别名: monobenzyl isophthalate；3-((benzyloxy)carbonyl)benzoic acid；Isophthalic acid benzyl ester；3-phenylmethoxycarbonylbenzoic acid
• CAS: 113266-88-9
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: AJGDGCHSUWBVKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  iso-phthalic acid monobenzyl ester 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 benzyl 3-(phenylcarbamoyl)benzoate
  参考文献：
  名称：

  Development of 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors

  摘要：

  Human 5-lipoxygenase (5-LOX) is a well-validated target for anti-inflammatory therapy. Development of novel 5-LOX inhibitors with higher activities is highly demanded. In previous study, we have built a model for the active conformation of human 5-LOX, and identified naphthalen-1-yl 3,5-dinitrobenzoate (JMC-4) as a 5-LOX inhibitor by virtual screening. In the present work, 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors were developed. Twenty aryl 3,5-dinitrobenzoates, N-aryl 3,5-dinitrobenzamides and analogues were designed and synthesized. Several of them were found with significantly increased activities according to cell-free assay and human whole blood assay. The structure-activity relationship study may provide useful insights for designing effective 5-LOX inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.008
• 作为产物：
  描述：

  isophthalic Acid dibenzyl ester 以75%的产率得到iso-phthalic acid monobenzyl ester
  参考文献：
  名称：

  1,1-Alkanediol dicarboxylate linked antibacterial agents

  摘要：

  有用的抗菌剂，其中通过1,1-烷二醇二羧酸酯连接了青霉素和/或β-内酰胺酶抑制剂，其化学公式为##STR1##，其中A是某些二羧酸的残基，R.sup.3是H或(C.sub.1-C.sub.3)，n是0或1，当n为0时，R是P或B，R.sup.1是某些酯的残基，H或其盐；当n为1时，R和R.sup.1中的一个为P，另一个为B，P为##STR2##，其中R.sup.2是H或某些酰基团，B是β-内酰胺酶抑制羧酸的残基；其使用方法、药物组合物及其生产中有用的中间体。

  公开号：

  US04457924A1

文献信息

• Pyrtriazoles, a Novel Class of Store-Operated Calcium Entry Modulators: Discovery, Biological Profiling, and in Vivo Proof-of-Concept Efficacy in Acute Pancreatitis
  作者：Beatrice Riva、Alessia Griglio、Marta Serafini、Celia Cordero-Sanchez、Silvio Aprile、Rosanna Di Paola、Enrico Gugliandolo、Dalia Alansary、Isabella Biocotino、Dmitry Lim、Giorgio Grosa、Ubaldina Galli、Barbara Niemeyer、Giovanni Sorba、Pier Luigi Canonico、Salvatore Cuzzocrea、Armando A. Genazzani、Tracey Pirali

  DOI：10.1021/acs.jmedchem.8b01512

  日期：2018.11.8

  a number of disorders, spanning from immune disorders to acute pancreatitis and have been suggested to be druggable targets. In the present contribution, we exploited the click chemistry approach to synthesize a class of SOCE modulators where the arylamide substructure that characterizes most inhibitors so far described is substituted by a 1,4-disubstituted 1,2,3-triazole ring. Within this series, inhibitors

  近年来，介导储库操纵性钙进入（SOCE，即细胞感知内质网腔内钙减少并诱导钙穿过质膜进入的能力）的通道与许多疾病有关，其范围从急性胰腺炎的免疫疾病已被认为是可治疗的目标。在目前的贡献中，我们利用点击化学方法合成了一类SOCE调节剂，其中表征到目前为止所描述的大多数抑制剂的芳基酰胺亚结构被1,4-二取代的1,2,3-三唑环取代。在该系列中，已鉴定出SOCE的抑制剂，并且证明了最佳化合物在急性胰腺炎的动物模型中有效，该疾病以SOCE的过度激活为特征。惊人地
• Acetyl-BINOL as mimic for chiral β-diketonates: a building block for new modular ligands
  作者：Robert von Rönn、Jens Christoffers

  DOI：10.1016/j.tet.2010.11.037

  日期：2011.1

  six-membered chelates with transition metal ions. The second hydroxy-function was submitted to esterification with several carboxylic acids bearing another donor function, thus, new tridentate chiral ligands were obtained. Out of this library the l-proline-α-acetyl-(S)-BINOL-ester was identified to be most effective for the titanium-mediated addition of Et2Zn to PhCHO yielding the respective secondary

  α-乙酰基-（S）-BINOL是通过邻位锂化和随后的乙缩醛保护的（S）-BINOL乙酰化制备的。该化合物的β-羟基酮部分在本文中是β-二酮酸酯的结构模拟物，并与过渡金属离子形成六元螯合物。将第二羟基官能团与带有另一种给体功能的几种羧酸进行酯化反应，从而获得了新的三齿手性配体。从该文库中，鉴定出1-脯氨酸-α-乙酰基-（S）-BINOL-酯对于钛介导的Et 2 Zn向PhCHO的添加最有效，从而产生相应的仲醇，ee最高可达93％，这比使用（S）-BINOL本身。除了对溶剂的依赖性（最好使用MeCN）外，正确选择抗衡离子也很重要：三氟乙酸根与溴离子的阴离子交换显着提高了对映选择性。
• Reactive immunization elicits catalytic antibodies for polyester hydrolysis
  作者：Da-Wei Chen、Robert J. Kubiak、Jon A. Ashley、Kim D. Janda

  DOI：10.1039/b105412k

  日期：2001.11.1

  In the search for biocatalysts for degradation of nonnatural polymers, reactive immunization with haptens 7 and 11 was used to prepare catalytic antibodies capable of cleaving short oligomeric esters, as well as the insoluble polyester 25. These antibodies were found to be highly specific and efficient esterases for oligomers. Triester 24 was preferentially hydrolyzed by an endo-cleavage pathway, however

  在寻找用于降解非天然聚合物的生物催化剂时，用半抗原7和11进行反应性免疫制备了能够裂解短的低聚酯以及不溶性聚酯25的催化抗体。发现这些抗体是针对寡聚物的高度特异性和有效的酯酶。三酯24优先通过内切途径水解，但是，使用较高分子量的聚合物25则无法观察到位点特异性。由于物理限制，抗体对不溶性聚合物25的催化效率受到限制。
• Design, synthesis and in vitro evaluation of novel uni- and bivalent ligands for the cannabinoid receptor type 1 with variation of spacer length and structure
  作者：Guozheng Huang、Daniela Pemp、Patricia Stadtmüller、Martin Nimczick、Jörg Heilmann、Michael Decker

  DOI：10.1016/j.bmcl.2014.07.038

  日期：2014.9

  Using rimonabant, a potent inverse agonist for cannabinoid receptor type 1 (CB1R), as parent ligand, a series of novel univalent and bivalent ligands were designed by variation of spacer length and its chemical structure. The ligands synthesized were evaluated for affinity and selectivity by radioligand displacement and a functional steady-state GTPase assay. The results showed the nature of the spacer

  使用1型大麻素受体（CB 1 R）的强效反向激动剂利莫那班作为母体配体，通过改变间隔区的长度及其化学结构，设计了一系列新颖的单价和二价配体。通过放射性配体置换和功能性稳态GTPase分析评估合成的配体的亲和力和选择性。结果表明，间隔子的性质会影响生物学读数。尽管所有化合物的亲和力均显着低于利莫那班，但这一事实可用于证明亲和力和选择性受间隔物的化学结构和长度影响，并可能有助于设计其他GPCR受体的二价探针。
• Amino Acid Binding by 2-(Guanidiniocarbonyl)pyridines in Aqueous Solvents: A Comparative Binding Study Correlating Complex Stability with Stereoelectronic Factors
  作者：Carsten Schmuck、Uwe Machon

  DOI：10.1002/chem.200400652

  日期：2005.2.4

  these compounds bind amino acids (carboxylate forms) in aqueous DMSO with association constants ranging from K = 30 to 460 M(-1) as determined by NMR titration experiments. The differences in the complex stabilities can be correlated with steric and electrostatic effects with the aid of calculated complex structures. For example, the electrostatic repulsion between the pyridine nitrogen lone pair and

  已合成了一系列胍基碘羰基吡啶受体，这些化合物结合DMSO水溶液中的氨基酸（羧酸盐形式），其缔合常数范围为K = 30至460 M（-1），这是通过NMR滴定实验确定的。借助计算出的复杂结构，可以将复杂稳定性的差异与空间效应和静电效应相关联。例如，吡啶氮孤对和结合的羧酸根之间的静电排斥使阴离子结合的效率比我们先前引入的用于水中羧酸根结合的类似吡咯受体的效率低。此外，如2b中的受体侧链与结合的底物之间的空间相互作用也不利于络合。