isobutyric acid (3S,6S,7R,8R)-3-amino-8-benzyl-6-methyl-4,9-dioxo-[1,5]dioxonane-7-yl ester | 210300-07-5

• 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: isobutyric acid (3S,6S,7R,8R)-3-amino-8-benzyl-6-methyl-4,9-dioxo-[1,5]dioxonane-7-yl ester
• 英文别名: [(3S,6S,7R,8R)-3-amino-8-benzyl-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate
• CAS: 210300-07-5
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: WGUFEPOUARSZOH-UKMLZYKCSA-N

物化性质

• 沸点：
  562.1±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  isobutyric acid (3S,6S,7R,8R)-3-amino-8-benzyl-6-methyl-4,9-dioxo-[1,5]dioxonane-7-yl ester 在 palladium on activated charcoal 、 氢气 、 乙酸酐 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 isobutyric acid (3S,4R,7R,8R,9S)-7-benzyl-3-(3-formylamino-2-hydroxybenzoylamino)-9-methyl-2,6-dioxo-[1,5]dioxonan-8-yl ester
  参考文献：
  名称：

  Evaluation of Inhibitory Activities of UK-2A, an Antimycin-Type Antibiotic, and Its Synthetic Analogues against the Production of Anti-inflammatory Cytokine IL-4

  摘要：

  The inhibitory activities of the antimycin-class antibiotics UK-2A, antimycin A, and splenocin B against the production of anti-inflammatory cytokine IL-4, which is related to IgE-mediated allergic responses in rat basophilic leukemia (RBL-2H3) cells, were evaluated. Although antimycin A and splenocin B showed cytotoxicity at concentrations at which IL-4 release from the cells was restricted, UK-2A was found to restrict IL-4 release without cytotoxicity. Three UK-2A analogues (4-6) were then synthesized and assessed. Compound 5 restricted IL-4 release dose-dependently without cytotoxicity, and its effect was more potent than that of UK-2A.

  DOI：

  10.1021/acs.jnatprod.8b00559
• 作为产物：
  描述：

  (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid benzyl ester 在 palladium hydroxide - carbon 吡啶 、 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 氢气 、 氟化氢吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 三氟乙酸 作用下， 以 吡啶 为溶剂， 生成 isobutyric acid (3S,6S,7R,8R)-3-amino-8-benzyl-6-methyl-4,9-dioxo-[1,5]dioxonane-7-yl ester
  参考文献：
  名称：

  抗真菌双内酯UK-2A的对映选择性全合成：相对构型和绝对构型的确定

  摘要：

  描述了抗真菌双内酯UK-2A的合成。除了为这种有效的抗真菌抗生素提供可行的合成途径外，这还使我们能够确定九元环中相对构型和绝对构型的分配。

  DOI：

  10.1016/s0040-4039(98)00796-5

文献信息

• SYNTHESIS AND USE OF ISOTOPICALLY LABELED MACROCYCLIC COMPOUNDS
  申请人：DOW AGROSCIENCES LLC

  公开号：US20140186873A1

  公开（公告）日：2014-07-03

  Disclosed herein are isotopically labeled antifungal antibiotics and related compounds. Also disclosed are methods for synthesizing these isotopically labeled molecules and using the same to study the distribution of these compounds in the biosphere as well as the products formed by the breakdown of these isotopically labeled compounds.

  本文披露了同位素标记的抗真菌抗生素和相关化合物。还披露了合成这些同位素标记分子的方法，并利用它们研究这些化合物在生物圈中的分布，以及这些同位素标记化合物降解产生的产物。
• Total synthesis of the antifungal dilactones UK-2A and UK-3A: The determination of their relative and absolute configurations, analog synthesis and antifungal activities
  作者：Masanao Shimano、Noriyuki Kamei、Tetsuo Shibata、Kiyoshi Inoguchi、Nobuko Itoh、Takashi Ikari、Hisato Senda

  DOI：10.1016/s0040-4020(98)00777-7

  日期：1998.10

  The synthesis of the antifungal dilactones, UK-2A and UK-3A, is described. In addition to providing a workable synthetic route to these potent antifungal antibiotics, this has allowed us to determine the assignment of the relative and absolute configurations in the nine-membered ring. Furthermore, UK-2A analogs were also synthesized and evaluated their antifungal activities and cytotoxic activities along with UK-2A, (2R, 3R, 4S, 7R)-UK-2A, UK-3A, (2R, 3R, 4S, 7R)-UK-3A, and antimycin A. The structural requirements for the selective cytotoxicity against yeasts and filamentous fungi will also be suggested. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Semi-synthesis and biological evaluation of analogues of UK-2A, a novel antifungal antibiotic from Streptomyces sp. 517-02
  作者：Yoshinosuke Usuki、Koichi Mitomo、Noriko Adachi、Xu Ping、Ken-Ichi Fujita、Osamu Sakanaka、Katsuharu Iinuma、Hideo Iio、Makoto Taniguchi

  DOI：10.1016/j.bmcl.2005.02.065

  日期：2005.4

  Several analogues of UK-2A, a novel antifungal antibiotic isolated from Streptomyces sp. 517-02, were semi-synthesized for structure-activity studies. In vitro antifungal activities of these compounds against Saccharomyces cerevisiae IFO 0203 were evaluated by the conventional paper disk method. Several derivatives exhibited growth inhibitory activity similar to UK-2A. (c) 2005 Elsevier Ltd. All rights reserved.
• US9482661B2
  申请人：——

  公开号：US9482661B2

  公开（公告）日：2016-11-01
• Enantioselective total synthesis of the antifungal dilactone, UK-2A: The determination of the relative and absolute configurations
  作者：Masanao Shimano、Tetsuo Shibata、Noriyuki Kamei

  DOI：10.1016/s0040-4039(98)00796-5

  日期：1998.6

  The synthesis of the antifungal dilactone, UK-2A, is described. In addition to providing a workable synthetic route to this potent antifungal antibiotic, this has allowed us to determine the assignment of the relative and absolute configurations in the nine-membered ring.

  描述了抗真菌双内酯UK-2A的合成。除了为这种有效的抗真菌抗生素提供可行的合成途径外，这还使我们能够确定九元环中相对构型和绝对构型的分配。