3-(2-methylphenyl)pentan-1,5-dioic acid | 59577-81-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(2-methylphenyl)pentan-1,5-dioic acid
• 英文别名: 3-(o-tolyl)pentanedioic acid；3-(2-methylphenyl)glutaric acid；3-(2-methylphenyl)pentane-1,5-diacid；3-(2-methylphenyl)pentanedioic acid
• CAS: 59577-81-0
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: VRSPECQGUYEYDD-UHFFFAOYSA-N

物化性质

• 沸点：
  376.6±27.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-methylphenyl)pentan-1,5-dioic acid 在 氯化亚砜 、 硼烷四氢呋喃络合物 、 (-)-di-p-toluoyl-L-tartaric acid 、 sodium ethanolate 、 尿素 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 73.5h， 生成 (-)-2-(4-(2-methylphenyl)piperidino)cyclohexanol
  参考文献：
  名称：

  Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor

  摘要：

  We synthesized methylvesamicol analogs 13-16 and investigated the binding characteristics of 2-[4-phenylpiperidino]cyclohexanol (vesamicol) and methylvesamicol analogs 13-16, with a methyl group introduced into the 4-phenylpiperidine moiety, to sigma receptors (sigma-1, sigma-2) and to vesicular acetylcholine transporters (VAChT) in membranes of the rat brain and liver. In competitive inhibition studies, (-)-o-methylvesamicol [(-)-OMV] (13) (K-i = 6.7 nM), as well as (-)-vesamicol (K-i = 4.4 nM), had a high affinity for VAChT. (+)-p-Methylvesamicol [(+)-PMV] (16) (K-i = 3.0 nM), as well as SA4503 (K-i = 4.4 nM), reported as a sigma-1 mapping agent for positron emission tomography (PET), had a high affinity for the sigma-1 receptor. The binding affinity of (+)-PMV (1-16) for the sigma-1 receptor (K-i = 3.0 nM) was about 13 times higher than that for the sigma-2 (sigma-2) receptor (K-i = 40.7 nM). (+)-PMV (16) (K-i = 199 nM) had a much lower affinity for VAChT than SA4503 (K-i = 50.2 nM) and haloperidol (K-i = 41.4 nM). These results showed that the binding characteristics of (-)-OMV (13) to VAChT were similar to those of (-)-vesamicol and that (+)-PMV (16) bound to the sigma-1 receptor with high affinity. In conclusion, (-)-OMV (13) and (+)-PMV (16). which had a Suitable structure, with a methyl group for labeling with C-11, may become not only a new VAChT ligand and a new type of sigma receptor ligand, respectively, but may also become a new target compound of VAChT and the sigma-1 receptor radioligand for PET, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.044
• 作为产物：
  描述：

  2-溴苯甲醛乙烯醛 在 四氢吡咯 、 盐酸 、 sodium hydride 、 magnesium 、 溶剂黄146 、 丙酮 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 79.58h， 生成 3-(2-methylphenyl)pentan-1,5-dioic acid
  参考文献：
  名称：

  Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor

  摘要：

  We synthesized methylvesamicol analogs 13-16 and investigated the binding characteristics of 2-[4-phenylpiperidino]cyclohexanol (vesamicol) and methylvesamicol analogs 13-16, with a methyl group introduced into the 4-phenylpiperidine moiety, to sigma receptors (sigma-1, sigma-2) and to vesicular acetylcholine transporters (VAChT) in membranes of the rat brain and liver. In competitive inhibition studies, (-)-o-methylvesamicol [(-)-OMV] (13) (K-i = 6.7 nM), as well as (-)-vesamicol (K-i = 4.4 nM), had a high affinity for VAChT. (+)-p-Methylvesamicol [(+)-PMV] (16) (K-i = 3.0 nM), as well as SA4503 (K-i = 4.4 nM), reported as a sigma-1 mapping agent for positron emission tomography (PET), had a high affinity for the sigma-1 receptor. The binding affinity of (+)-PMV (1-16) for the sigma-1 receptor (K-i = 3.0 nM) was about 13 times higher than that for the sigma-2 (sigma-2) receptor (K-i = 40.7 nM). (+)-PMV (16) (K-i = 199 nM) had a much lower affinity for VAChT than SA4503 (K-i = 50.2 nM) and haloperidol (K-i = 41.4 nM). These results showed that the binding characteristics of (-)-OMV (13) to VAChT were similar to those of (-)-vesamicol and that (+)-PMV (16) bound to the sigma-1 receptor with high affinity. In conclusion, (-)-OMV (13) and (+)-PMV (16). which had a Suitable structure, with a methyl group for labeling with C-11, may become not only a new VAChT ligand and a new type of sigma receptor ligand, respectively, but may also become a new target compound of VAChT and the sigma-1 receptor radioligand for PET, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.044
• 作为试剂：
  描述：

  sodium hydroxide 、 盐酸 、 3-(2-methylphenyl)pentan-1,5-dioic acid 、 在 ice 、 水 、 3-(2-methylphenyl)pentan-1,5-dioic acid 、 petrol ether 作用下， 以 乙酰氯 、 二氯甲烷 为溶剂， 反应 16.0h， 以to provide 3-(2-methylphenyl)glutaric anhydride (6.79 g) as colourless solid的产率得到4-(2-methylphenyl)dihydropyran-2,6-dione
  参考文献：
  名称：

  ALLOSTERIC PROTEIN KINASE MODULATORS

  摘要：

  该发明提供了特定的小分子化合物，可以对AGC蛋白激酶和Aurora蛋白激酶家族的活性进行变构调节或调节蛋白质-蛋白质相互作用，以及制备它们的方法，包括它们的制药组合物，以及它们用于制备治疗与AGC蛋白激酶或Aurora家族蛋白激酶异常活性相关的疾病的药物的用途。

  公开号：

  US20120046307A1

文献信息

• [EN] ALLOSTERIC PROTEIN KINASE MODULATORS<br/>[FR] MODULATEURS DE PROTÉINE KINASE ALLOSTÉRIQUE
  申请人：UNIV SAARLAND

  公开号：WO2010043711A1

  公开（公告）日：2010-04-22

  The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

  该发明提供特定的小分子化合物，这些化合物能够变构调节AGC蛋白激酶的活性或调节Aurora家族蛋白激酶的蛋白-蛋白相互作用，提供这些化合物的制备方法，包含这些化合物的药物组合物，以及它们用于制备治疗和预防与AGC蛋白激酶或Aurora家族蛋白激酶异常活动相关疾病的药物的应用。
• Allosteric protein kinase modulators
  申请人：Engel Matthias

  公开号：US08912186B2

  公开（公告）日：2014-12-16

  The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

  本发明提供了一种特定的小分子化合物，可以变构地调节AGC蛋白激酶和Aurora家族蛋白激酶的活性或调节它们之间的蛋白质相互作用，以及制备它们的方法、包含它们的制药组合物，以及它们用于制备治疗与AGC蛋白激酶或Aurora家族蛋白激酶异常活性相关的疾病的药物。
• Ligand for Vesicular Acetylcholine Transporter
  申请人：Shiba Kazuhiro

  公开号：US20090163461A1

  公开（公告）日：2009-06-25

  The present invention provides a novel compound represented by the formula (I): wherein R 1 and R 2 are as defined in the specification, or a salt thereof, which is useful as a reagent (radiotracer) for VAChT mapping and the like, and can be used for positron emission tomography (PET), and a production method of the compound. Moreover, the present invention provides a diagnostic reagent for diagnosing cholinergic neurodegenerative disorders (e.g., Alzheimer's disease, memory disorder, learning disorder, schizophrenia, cognitive dysfunction, hyperactivity disorder, anxiety neurosis, depression, analgia, Parkinson's disease and the like) and the like, which contains the aforementioned compound.

  本发明提供了一种新的化合物，其化学式为（I），其中R1和R2如规范中定义，或其盐，该化合物可用作VAChT映射等试剂（放射性示踪剂），可用于正电子发射断层扫描（PET），以及该化合物的制备方法。此外，本发明还提供了一种诊断试剂，用于诊断胆碱能神经退行性疾病（例如，阿尔茨海默病、记忆障碍、学习障碍、精神分裂症、认知功能障碍、多动症、焦虑神经症、抑郁症、无痛觉症、帕金森病等），其中包含上述化合物。
• Catalytic Enantioselective Desymmetrization of Prochiral Triacylamines via Pseudopeptidic Guanidine–Guanidinium Catalysis
  作者：Hu Qu、Xin-Shen Liang、Wen-Juan Wang、Xian-He Zhao、Yu-Hua Deng、Xian-Tao An、Wen-Dao Chu、Xiang-Zhi Zhang、Chun-An Fan

  DOI：10.1021/acs.orglett.2c02785

  日期：2022.9.23

  Triacylamines with Cs symmetry have been explored in asymmetric organocatalysis, leading to the development of a novel catalytic enantioselective desymmetrization of prochiral triacylamines by methanolysis under the catalysis of chiral pseudopeptidic guanidine–guanidinium salt having a weakly coordinating anion. This organocatalytic methodology provides an effective approach to the synthetically useful

  已经在不对称有机催化中探索了具有C s对称性的三酰基胺，从而在具有弱配位阴离子的手性假肽胍-胍盐的催化下通过甲醇分解开发了一种新的催化对映选择性去对称化前手性三酰基胺。这种有机催化方法为合成有用的具有 1,5-二羰基部分的手性酰亚胺酯提供了一种有效的方法，其合成潜力已在两种 GABA 类似药物的不对称合成中得到体现，( R )-巴氯芬·HCl 和 ( S )-普瑞巴林。
• Switchable divergent di- or tricarboxylation of allylic alcohols with CO2
  作者：Bo Yu、Yi Liu、Han-Zhi Xiao、Shu-Rong Zhang、Chuan-Kun Ran、Lei Song、Yuan-Xu Jiang、Chang-Fu Li、Jian-Heng Ye、Da-Gang Yu

  DOI：10.1016/j.chempr.2023.12.005

  日期：2024.3

  Visible-light-driven switchable divergent di- or tricarboxylation of allylic alcohols with CO is realized to selectively upgrade multiple CO units to polycarboxylic acids. The derivatization of corresponding polycarboxylic acids could deliver the potential functional materials in luminescence and biomaterials.

  实现了烯丙醇与CO的可见光驱动可切换发散二羧化或三羧化，选择性地将多个CO单元升级为多元羧酸。相应的聚羧酸的衍生化可以在发光和生物材料中提供潜在的功能材料。