(Z)-2-methyl-4-(3,4,5-trimethoxybenzylidene)oxazol-5(4H)-one | 92249-24-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-2-methyl-4-(3,4,5-trimethoxybenzylidene)oxazol-5(4H)-one
• 英文别名: 2-Methyl-4-(3,4,5-trimethoxy-benzylidene)-4H-oxazol-5-one；(4Z)-2-methyl-4-[(3,4,5-trimethoxyphenyl)methylidene]-1,3-oxazol-5-one
• CAS: 92249-24-6
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: BKYSSHFIJZZSSX-YHYXMXQVSA-N

物化性质

• 熔点：
  161-164 °C
• 沸点：
  403.7±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)
• 溶解度：
  25.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-2-methyl-4-(3,4,5-trimethoxybenzylidene)oxazol-5(4H)-one 在 盐酸 、 sodium hydroxide 作用下， 生成 2-氧代-3-(3,4,5-三甲氧基苯基)丙酸
  参考文献：
  名称：

  Potent, Selective Tetrahydro-β-carboline Antagonists of the Serotonin 2B (5HT_2B) Contractile Receptor in the Rat Stomach Fundus

  摘要：

  A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (-log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-beta-carboline antagonists are able to discriminate among the 5HT(2) family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-beta-carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.

  DOI：

  10.1021/jm960062t
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 反应 8.0h， 以71%的产率得到(Z)-2-methyl-4-(3,4,5-trimethoxybenzylidene)oxazol-5(4H)-one
  参考文献：
  名称：

  A Modified Synthesis of (±)-β-Aryllactic acids

  摘要：

  据报道，丹参中活性成分的外消旋形式，即（±）-ß-(3,4-二羟基苯基)乳酸[(±)-3-(3,4-二羟基苯基)-2-羟基丙酸]及其七种外消旋衍生物已成功合成。

  DOI：

  10.1055/s-1992-26228

文献信息

• Tailored Peptide Phenyl Esters Block ClpXP Proteolysis by an Unusual Breakdown into a Heptamer–Hexamer Assembly
  作者：Markus Lakemeyer、Eva Bertosin、Friederike Möller、Dóra Balogh、Ralf Strasser、Hendrik Dietz、Stephan A. Sieber

  DOI：10.1002/anie.201901056

  日期：2019.5.20

  binding of probes arrested ClpXP in an unprecedented heptamer–hexamer assembly, in which the two heptameric ClpP rings are dissociated from each other. At the same time, the affinity between ClpX and ClpP increased, leading to inhibition of both enzymes. This conformational arrest is beneficial for the consolidated shutdown of ClpXP, as well as for the study of the oligomeric state during its catalytic

  蛋白水解复合物ClpXP是细菌稳态和发病机理的基础。由于其构象的灵活性，有效的ClpXP抑制剂的开发具有挑战性，迫切需要新的工具来解密其复杂的调控。在这里，我们提出了基于氨基酸的苯基酯作为分子探针，以研究金黄色葡萄球菌的ClpXP复合物的活性和低聚。系统地筛选（R）和（S）氨基酸导致化合物显示出有效的抑制作用，并刺激ClpXP介导的蛋白水解作用。探针的亚化学计量结合使ClpXP停滞在前所未有的七聚体-六聚体组装中，其中两个七聚体ClpP环彼此解离。同时，ClpX和ClpP之间的亲和力增加，导致两种酶的抑制作用。这种构象停滞对于ClpXP的合并关闭以及在其催化循环期间研究低聚状态是有益的。
• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
  申请人：Chung Hae Young

  公开号：US20140023603A1

  公开（公告）日：2014-01-23

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白皮肤、抗氧化和PPAR活性的新化合物及其医疗用途，该化合物具有美白皮肤的活性，可抑制酪氨酸酶，因此适用于用于美白皮肤的药物组合物或化妆品；具有抗氧化活性，因此适用于预防和治疗皮肤老化；具有PPAR活性，特别是PPARα和PPARγ活性，因此适用于用于预防和治疗肥胖、代谢性疾病或心血管疾病的药物组合物或保健食品。
• Practical Preparation of <i>Z</i>‐α‐(<i>N</i>‐Acetylamino)‐ and <i>Z</i>‐α‐(<i>N</i>‐Benzoylamino)‐α,β‐unsaturated Acids
  作者：Branko S. Jursic、Sarada Sagiraju、Dustin K. Ancalade、Traneil Clark、Edwin D. Stevens

  DOI：10.1080/00397910701265895

  日期：2007.5.1

  An efficient two‐step synthetic procedure for the preparation of numerous variations of N‐protected α,β‐unsaturated α‐amino acids and their corresponding esters from N‐protected glycine and either aliphatic or aromatic aldehydes was developed. The reaction involved cyclization of the N‐protected glycine into oxazolone, condensation with the aldehyde, and ring opening with a base.

  摘要 开发了一种有效的两步合成程序，用于从 N-保护的甘氨酸和脂肪族或芳香族醛制备 N-保护的 α,β-不饱和 α-氨基酸及其相应的酯的多种变体。该反应包括将 N 保护的甘氨酸环化为恶唑酮、与醛缩合以及与碱开环。
• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREOF
  申请人：Pusan National University Industry-University Cooperation Foundation

  公开号：US20160102065A1

  公开（公告）日：2016-04-14

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白、抗氧化和PPAR活性的新化合物及其医疗用途。该化合物具有抑制酪氨酸酶的美白活性，因此可用于美白药物组合物或化妆品产品；具有抗氧化活性，因此可用于预防和治疗皮肤老化；具有PPAR活性，特别是PPARα和PPARγ活性，因此可用于有效预防和治疗肥胖症、代谢疾病或心血管疾病的药物组合物或保健食品。
• Tyagi, O D; Boll, P M; Parmar, V S, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 12, p. 851 - 854
  作者：Tyagi, O D、Boll, P M、Parmar, V S、Taneja, Poonam、Singh, S K

  DOI：——

  日期：——