(3R)-1-[(S)-1-phenylethyl]mevalonamide | 946831-51-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R)-1-[(S)-1-phenylethyl]mevalonamide
• 英文别名: (3R)-3,5-dihydroxy-3-methyl-N-[(1S)-1-phenylethyl]pentanamide
• CAS: 946831-51-2
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: YNEAYIPGJNBOCO-SMDDNHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3R)-1-[(S)-1-phenylethyl]mevalonamide 在 吡啶 作用下， 反应 24.0h， 生成 (3R)-5-O-acetyl-1-[(S)-phenylethyl]mevalonamide
  参考文献：
  名称：

  子囊菌，大叶黄杨甲壳菌的免疫调节成分和大蛋白D的绝对结构的修正。

  摘要：

  以甲壳虫大叶古生菌的EtOAc提取物的免疫调节活性为指导进行分级分离，提供了两种新的天然产物，即4'-oxomacrophorin D（1）和4'-oxomacrophorin A（2），作为这种真菌的免疫抑制成分[1： 3]的3-羟基-3-甲基戊二酰（HMG）缀合物。包含1和2的绝对构型的结构是根据1与大蛋白D的化学相关性确定的（3）。3中HMG部分的绝对构型已从3R修改为3S。

  DOI：

  10.1021/np010152n
• 作为产物：
  描述：

  氧氟草苷E 在 锂硼氢 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 (3R)-1-[(S)-1-phenylethyl]mevalonamide
  参考文献：
  名称：

  3-Hydroxy-3-Methylglutaryl Flavonol Glycosides from Oxytropis falcata

  摘要：

  Five new 3-hydroxy-3-methylglutaryl (HMG) flavonol 3-O-glycosides, named oxytroflavosides A-E (1-5), and two new rhamnocitrin 3-O-glycosides, oxytroflavosides F and G (6 and 7) were isolated from the n-BuOH-soluble fraction of an EtOH extract of Oxytropis falcata together with seven known kaempferol glycosides (8-14), of which six were isolated from the genus Oxytropis for the first time. The structures of these compounds were elucidated by spectroscopic techniques and chemical methods. The absolute configuration of HMG in compounds 1-5 was determined to be S through spectroscopic analysis of the mevalonamide obtained by amidation and reduction of the HMG moiety. Compounds 1-10 were evaluated for anti-inflammatory activities using lipopolysaccharide-induced RAW 264.7 cells, but none of them showed inhibitory effects on NO production.

  DOI：

  10.1021/np300292f

文献信息

• New C-2 diastereomers of flavanone glycosides conjugated with 3-hydroxy-3-methylglutaric acid from the pericarp of Citrus grandis (L.) Osbeck
  作者：Shuang-Gang Ma、Ru-Bing Wang、Wen-Rui Li、Yun-Bao Liu、Jing Qu、Yong Li、Xiao-Jing Wang、Song Xu、Shi-Shan Yu

  DOI：10.1016/j.bioorg.2018.06.024

  日期：2018.10

  Two new 3-hydroxy-3-methylglutaryl (HMG) flavanone 7-O-diglycosides, cigranosides A and B (1 and 2), the known naringenin 7-(2′′-α-rhamnosyl-6′′-(3′′′′-hydroxy-3′′′′-methylglutaryl)-glucoside (melitidin, 3), their common biosynthetic precursor flavanone 7-O-diglycoside (naringin, 4), and one known flavone 7-O-diglycoside (rhoifolin, 5) were isolated from the pericarp of Citrus grandis (L.) Osbeck.

  两种新的3-羟基-3-甲基戊二酮（HMG）黄烷酮7- O-二糖苷，香茅苷A和B（1和2），即已知的柚皮苷7-（2''- α-鼠李糖基-6''-（3' ′′′-羟基-3′′′′-甲基谷氨酰胺）-葡糖苷（melitidin，3），其常见的生物合成前体黄烷酮7- O- diglycoside（naringin，4）和一种已知的黄酮7- O- diglycoside（rhoifolin，5）是从柑桔皮的果皮中分离得到的，并通过光谱和化学技术对其结构进行了说明，该化合物的C-2非对映异构体的相对比例和绝对构型1，2和4通过在线正相HPLC-CD使用Chiralcel柱测定。化合物中的HMG片段的绝对构型1 - 3被分配到小号通过酰胺化和还原的HMG部分的获得的mevalonamide的光谱分析。化合物的NO抑制活性1 - 5使用脂多糖诱导的RAW264.7细胞进行了评价。化合物1 - 5不是细胞毒性RAW264
• Revised chirality of the acyl group of 8′-O-(3-hydroxy-3-methylglutaryl)-8′-hydroxyabscisic acid
  作者：Tsunashi Kamo、Nobuhiro Hirai、Chiaki Matsumoto、Hajime Ohigashi、Mitsuru Hirota

  DOI：10.1016/j.phytochem.2004.07.012

  日期：2004.9

  ydroxyabscisic acid is a stable conjugate of the first metabolite of abscisic acid, 8'-hydroxyabscisic acid, that is spontaneously isomerized to phaseic acid. The chirality of the 3-hydroxy-3-methylglutaryl group of the conjugate was revised to S based on an HPLC analysis of the diastereomer derived from mevalonolactone obtained by reduction of the conjugate with lithium borohydride.

  8'-O-(3-Hydroxy-3-methylglutaryl)-8'-hydroxyabscisic acid 是脱落酸的第一种代谢物 8'-羟基脱落酸的稳定结合物，其自发异构化为相酸。基于通过用硼氢化锂还原缀合物获得的甲羟戊内酯衍生的非对映异构体的HPLC分析，将缀合物的3-羟基-3-甲基戊二酰基的手性修正为S。
• Anti-inflammatory Lanostane-Type Triterpene Acids from <i>Piptoporus </i><i>b</i><i>etulinus</i>
  作者：Tsunashi Kamo、Masashi Asanoma、Hisao Shibata、Mitsuru Hirota

  DOI：10.1021/np0300479

  日期：2003.8.1

  Six lanostane-type triterpene acids were isolated from the fruiting bodies of Piptoporus betulinus. They were identified as polyporenic acids A (1) and C (2), three derivatives of polyporenic acid A (3-5), and a novel compound, (+)-12 alpha,28-dihydroxy-3 alpha-(3'-hydroxy-3'-methylglutaryloxy)-24-methyllanosta-8,24(31)-dien-26-oic acid (6). All these compounds suppressed the 12-O-tetradecanoylphorbol-13-acetate

  从白果对虾的子实体中分离出了六种羊毛甾烷型三萜酸。它们被鉴定为多孔酸A（1）和C（2），多孔酸A的三种衍生物（3-5）和新型化合物（+）-12 alpha，28-dihydroxy-3 alpha-（3' -羟基-3'-甲基戊二酰氧基）-24-甲基羊毛脂-8,24（31）-二烯-26-油酸（6）。所有这些化合物在400 nmol /耳的应用下均能抑制12-O-十四烷酰phorbol-13-乙酸盐（TPA）引起的小鼠耳部水肿49-6％。
• C-Methylated flavanones from the rhizomes of Matteuccia intermedia and their α-glucosidase inhibitory activity
  作者：Xue Li、Ling-Juan Zhu、Jin-Peng Chen、Chen-Yu Shi、Li-Ting Niu、Xue Zhang、Xin-Sheng Yao

  DOI：10.1016/j.fitote.2019.04.002

  日期：2019.7

  One new flavanonol, demethylmatteucinol (1), and nine new flavanone glucoside derivatives, matteflavosides H-J (2-4) and matteuinterates A-F (5-10), were isolated from the rhizomes of Matteuccia intermedia C.Chr., along with 21 known flavanones (11-31). Notably, all of them contain C-methylation in the A-ring. The structures of the compounds were elucidated by spectroscopic methods and chemical derivatization

  从Matteuccia intermedia C.Chr。的根茎中分离出一种新的黄烷醇，去甲基麦角三醇（1）和九种新的黄烷酮葡糖苷衍生物，matteflavosides HJ（2-4）和matteuinterates AF（5-10），以及21种已知的黄烷酮。 （11-31）。值得注意的是，它们全部在A环中含有C-甲基化。通过光谱方法和化学衍生化阐明了化合物的结构。α-糖苷酶抑制试验表明，化合物12-17具有强抑制活性，IC50值为12.4-69.7μM，表明它们具有降血糖作用。
• A new reagent for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides. Synthesis of (R)- and (S)-β-carboxymethyl-β-methyl-β-lactones by asymmetric desymmetrization of HMGA anhydride
  作者：Kimiko Hashimoto、Jun-ichi Kitaguchi、Yasuhiro Mizuno、Tadao Kobayashi、Haruhisa Shirahama

  DOI：10.1016/0040-4039(96)00274-2

  日期：1996.3

  (R)- and (S)-β-carboxymethyl-β-methyl-β-lactones, new reagents for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides were developed through the asymmetric desymmetrization of HMGA anhydride. The reagent was smoothly reacted with various alkoxide without racemization to afford the desirable half-esters. On the other hand, the reaction with various amine in refluxing

  （R）-和（S）-β-羧甲基-β-甲基-β-内酯通过HMGA的不对称脱对称作用开发了用于制备手性HMGA（3-羟基-3-甲基戊二酸）酯和酰胺的新试剂酐。使试剂与各种醇盐平稳反应，而无需外消旋作用，得到所需的半酯。另一方面，在回流的甲苯中与各种胺的反应得到外消旋酰胺。使用试剂的相应甲酯制备了手性HMGA酰胺。