N-(4-methoxyphenethyl)-β-amino-α-hydroxy-amide | 1007566-96-2

• 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: N-(4-methoxyphenethyl)-β-amino-α-hydroxy-amide
• 英文别名: (2R,3S)-3-amino-2-hydroxy-N-[2-(4-methoxyphenyl)ethyl]-4-phenylbutanamide
• CAS: 1007566-96-2
• 化学式: C₁₉H₂₄N₂O₃
• 分子量: 328.411
• InChiKey: HFHOQIVCMVZDBT-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  84.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenethyl)-β-amino-α-hydroxy-amide 在 盐酸 、 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 sodium thiosulfate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (S)-N-(4-(4-methoxyphenethylamino)-3,4-dioxo-1-phenylbutan-2-yl)-6-hydroxy-7-methoxy-3-methyl-4-oxo-4H-chromene-2-carboxamide
  参考文献：
  名称：

  色酮-肽基杂合体作为抗杜氏利什曼原虫潜在药物的合理再利用、合成、体外和计算机研究

  摘要：

  摘要 合成了色酮-肽基杂合体系列，并合理地重新调整用途，以鉴定针对内脏利什曼病的潜在抗利什曼病。三种杂交体7c、7n和7h显示出潜在的 IC 50值（分别为 9.8、10 和 12 µM），与埃卢福辛 IC 50 (9.8 µM)相当，但效力低于米替福辛 IC 50 (3.5 µM)。使用人 THP-1 细胞对细胞毒性进行初步评估，发现色酮-肽杂合体7c和7n在高达 100 µM 时无细胞毒性，而埃吕福辛和米替福辛的 CC 50分别为 19.4 µM 和 >40 µM。计算机模拟研究指出，肽基部分的N - p-甲氧基苯乙基取代基以及色酮部分苯环的氧基取代功能是与Ld CALP 结合的关键因素。总之，这些发现表明色酮-肽基杂合体7c和7n作为潜在的和预期的非细胞毒性抗利什曼病命中化合物，可用于开发潜在的抗内脏利什曼病抗利什曼病药物。

  DOI：

  10.1080/14756366.2023.2229071

文献信息

• Design and synthesis of 4-quinolinone 2-carboxamides as calpain inhibitors
  作者：Dong Hyuk Nam、Kwang Seob Lee、Sang Hoon Kim、Sung Min Kim、Seo Yun Jung、Sung Hyun Chung、Hyoung Ja Kim、Nam Doo Kim、Changbae Jin、Yong Sup Lee

  DOI：10.1016/j.bmcl.2007.10.097

  日期：2008.1

  Calpains are involved in a variety of calcium-regulated cellular processes, such as signal transduction, cell proliferation, differentiation, and apoptosis. Excessive calpain activation contributes to serious cellular damage and has been reported in many pathological conditions. 4-Quinolinone 2-carboxamide derivatives were prepared and evaluated for mu-calpain inhibitory activities. Of the compounds synthesized, 3a and 3k, which possess a primary amide and 4-methoxyphenethyl amide at P-1' region, were found to most potently inhibit mu-calpain with IC50 values of 0.71 +/- 0.07 and 0.73 +/- 0.23 mu M, respectively. On the other hand, the incorporation of pyridine-containing amides decreased inhibitory activity. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of chromone carboxamide derivatives with antioxidative and calpain inhibitory properties
  作者：Sang Hoon Kim、Young Hoon Lee、Seo Yun Jung、Hyoung Ja Kim、Changbae Jin、Yong Sup Lee

  DOI：10.1016/j.ejmech.2011.02.025

  日期：2011.5

  The overactivation of mu-calpain can cause serious cell damage in several diseases. Furthermore, cell death in a number of neurodegenerative disorders is linked to the overproduction of reactive oxygen species. Therefore, antioxidants and mu-calpain inhibitors could have the therapeutic potentials to treat cell death related diseases. New chromone carboxamide derivatives 3 were synthesized to provide alternative mu-calpain inhibitors to compound 2, a conformationally constrained structural variant of MDL 28,170. Compounds 3h and 3l exhibited the most potent p-calpain inhibitory activities (IC50 = 0.09-0.10 mu M), and were comparable to 2 in this respect (IC50 = 0.07 mu M). Compound 31 showed both potent p-calpain inhibitory activity (IC50 = 0.28 mu M) and antioxidant activities in DPPH scavenging and lipid peroxidation inhibition assays. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Bestatin analogs-4-quinolinone hybrids as antileishmanial hits: Design, repurposing rational, synthesis, in vitro and in silico studies
  作者：Ahmed H.E. Hassan、Kazem Mahmoud、Trong-Nhat Phan、Moataz A. Shaldam、Chae Hyeon Lee、Yeon Ju Kim、Soo Bin Cho、Waleed A. Bayoumi、Selwan M. El-Sayed、Yeonwoo Choi、Suyeon Moon、Joo Hwan No、Yong Sup Lee

  DOI：10.1016/j.ejmech.2023.115211

  日期：2023.3

  their different molecular targets. Amongst type 1 bestatin analog-4-quinolone hybrids, hybrid 1e was identified as potential hit inhibiting growth of L. donovani promastigotes by 91 and 53% at 50 and 25 μM concentrations, respectively. Meanwhile, hybrid 2j was identified amongst type 2 bestatin analog-4-quinolone hybrids as potential hit compound inhibiting growth of L. donovani promastigotes by 50 and