苹果酸 4-甲酯 | 66178-02-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: 苹果酸 4-甲酯
• 中文别名: 苹果酸4-甲酯
• 英文名称: malic acid monomethyl ester
• 英文别名: l-malic acid β-monomethyl ester；l-Aepfelsaeure-β-monomethylester；(2s)-2-hydroxy-4-methoxy-4-oxobutanoic Acid
• CAS: 66178-02-7
• 化学式: C₅H₈O₅
• 分子量: 148.116
• InChiKey: ZJDXMXMEZZVUKO-VKHMYHEASA-N

物化性质

• 沸点：
  357.7±27.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  苹果酸 4-甲酯 在 sodium tetrahydroborate 、 二甲基硫 、 diborane(6) 作用下， 生成 (S)-3,4-二羟基丁酸甲酯
  参考文献：
  名称：

  Largazole Arrests Cell Cycle at G1 Phase and Triggers Proteasomal Degradation of E2F1 in Lung Cancer Cells

  摘要：

  Aberration in cell cycle has been shown to be a common occurrence in lung cancer, and cell cycle inhibitor represents an effective therapeutic strategy. In this study, we test the effects of a natural macrocyclic depsipeptide largazole on lung cancer cells and report that this compound potently inhibits the proliferation and clonogenic activity of lung cancer cells but not normal bronchial epithelial cells. Largazole arrests cell cycle at G1 phase with up-regulation of the expression of cyclin-dependent kinase inhibitor p21. Interestingly, largazole enhances the E2F1-HDAC1 binding affinity and induces a proteasomal degradation of E2F1, leading to suppression of E2F1 function in lung cancer but not normal bronchial epithelial cells. Because E2F1 is overexpressed in lung cancer tumor samples, these data indicate that largazole is an E2F1-targeting cell cycle inhibitor, which bears therapeutic potentials for this malignant neoplasm.

  DOI：

  10.1021/ml400093y
• 作为产物：
  描述：

  L-苹果酸二甲酯 在 sodium hydroxide 、 pig liver esterase 作用下， 生成 苹果酸 4-甲酯
  参考文献：
  名称：

  Use of enzymic hydrolysis of dimethyl malates for a short synthesis of tulipalin B and of its enantiomer

  摘要：

  DOI：

  10.1021/jo00207a054

文献信息

• A stereoselective approach to the δ-lactone fragment of the lankacidin antibiotics
  作者：Eric J. Thomas、Andrew C. Williams

  DOI：10.1039/c39870000992

  日期：——

  An approach to the synthesis of the lactone fragment of the lankacidin antibiotics is described which is based upon stereoselective modification of an L-aspartic acid derived β-lactam.

  描述了一种基于L-天冬氨酸衍生的β-内酰胺的立体选择性修饰的合成兰卡酸抗生素内酯片段的方法。
• Biologically active macrolides, compositions, and uses thereof
  申请人：The United States of America, as represented by the Secretary, Department of Health and Human Services

  公开号：US09139595B2

  公开（公告）日：2015-09-22

  The present invention provides a compound of the formula (I) or (II), wherein R1 is H, alkyl, alkenyl or aryl, R2 is H, alkyl or aryl, R3 is H, a alkyl, alkenyl or aryl, R4 and R4-R8 are independently R10, C(O)R10 or SO2R10, wherein R10 is H, alkyl, alkenyl or aryl, and R9 is R9a, C(O)R9a or SO2R9a, wherein R9a is H, alkyl, alkenyl or aryl. R9a can be unsubstituted or substituted with one or more oxo(═O), OR9b, OC(O)R9b, OSO2R9b, NHR9b, NHC(O)R9b and NHSO2R9b groups. R9b is H, alkyl, alkenyl, or aryl. R9b can be unsubstituted or substituted with one or more groups such as oxo(═O), OR9c, CO2R9c, CO2R9c and OC(O)R9c. R9c is H, or a unsubstituted or substituted alkyl, alkenyl or aryl. The present invention further provides a composition comprising at least one compound of the present invention and a pharmaceutically acceptable carrier, alone or in combination with at least one additional active agent. The present invention further provides a method of treating a condition treatable by the inhibition of vacuolar-type (H+)-ATPase and a method of treating cancer.

  本发明提供了式（I）或（II）的化合物，其中R1为H，烷基，烯基或芳基，R2为H，烷基或芳基，R3为H，烷基，烯基或芳基，R4和R4-R8独立地为R10，C（O）R10或SO2R10，其中R10为H，烷基，烯基或芳基，R9为R9a，C（O）R9a或SO2R9a，其中R9a为H，烷基，烯基或芳基。R9a可以是未取代的或取代的，取代基为一个或多个氧代（═O），OR9b，OC（O）R9b，OSO2R9b，NHR9b，NHC（O）R9b和NHSO2R9b基团。R9b为H，烷基，烯基或芳基。R9b可以是未取代的或取代的，取代基为一个或多个氧代（═O），OR9c，CO2R9c，CO2R9c和OC（O）R9c基团。R9c为H，或未取代或取代的烷基，烯基或芳基。本发明还提供了包含本发明中至少一种化合物和药学上可接受的载体的组合物，单独或与至少一种额外活性剂组合使用的组合物。本发明还提供了一种治疗可通过抑制液泡型（H +）-ATP酶治疗的疾病的方法和一种治疗癌症的方法。
• A Simple and Powerful tert-Butylation of Carboxylic Acids and Alcohols
  作者：Kosuke Namba、Chie Ogasa、Kimika Kayano

  DOI：10.1055/a-2161-9689

  日期：2024.1

  A simple and safe tert-butylation reaction was developed. Treatment of various free amino acids with 1.1 equivalents of bis(trifluoromethanesulfonyl)imide in tert-butyl acetate directly afforded tert-butyl esters with free amino groups quickly and in good yields. In addition, various carboxylic acids and alcohols without amino groups were converted into tert-butyl esters and ethers, respectively, in

  开发了一种简单且安全的叔丁基化反应。用1.1当量的双(三氟甲磺酰基)亚胺的乙酸叔丁酯溶液处理各种游离氨基酸，可以快速且高收率地直接得到具有游离氨基的叔丁酯。此外，在少量催化量的双(三氟甲磺酰基)亚胺存在下，各种不含氨基的羧酸和醇分别以高产率转化为叔丁基酯和醚。与传统方法相比，游离氨基酸、羧酸和醇的所有叔丁基化反应进行得更快并且产率更高。
• Synthesis of Novel β-Lactone Inhibitors of Fatty Acid Synthase
  作者：Robyn D. Richardson、Gil Ma、Yatsandra Oyola、Manuel Zancanella、Lynn M. Knowles、Piotr Cieplak、Daniel Romo、Jeffrey W. Smith

  DOI：10.1021/jm800321h

  日期：2008.9.11

  Fatty acid synthase (FAS) is necessary for growth and survival of tumor cells and is a promising drug target for oncology. Here, we report oil the syntheses and activity of novel inhibitors of the thioesterase domain of FAS. Using the structure of orlistat as a starting point, which contains a beta-lactone as the central pharmacophore, 28 novel congeners were synthesized and examined. Structural features such as the length of the alpha- and beta-alkyl chains, their chemical composition, and arnino ester substitutions were altered and tile resulting compounds explored for inhibitory activity toward the thioesterase domain of FAS. Nineteen congeners show improved potency for FAS in biochemical assays relative to orlistat. Three of that subset, including the natural product valilactone, also display all increased potency in inducing tumor cell death and improved solubility compared to orlistat. These findings Support the idea that all orlistat congener can be optimized for use in a preclinical drug design and for clinical drug development.
• Demondesir, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1851, vol. 33, p. 229
  作者：Demondesir

  DOI：——

  日期：——