iheyanone | 133908-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: iheyanone
• 英文别名: (S)-5-Isopropyl-4-methoxy-1H-pyrrol-2(5H)-one；(2S)-3-methoxy-2-propan-2-yl-1,2-dihydropyrrol-5-one
• CAS: 133908-08-4
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: CTMNTJJCOFENNG-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  iheyanone 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.67h， 生成
  参考文献：
  名称：

  Synthesis of Gallinamide A Analogues as Potent Falcipain Inhibitors and Antimalarials

  摘要：

  Analogues of the natural product gallinamide A were prepared to elucidate novel inhibitors of the falcipain cysteine proteases. Analogues exhibited potent inhibition of falcipain-2 (FP-2) and falcipain-3 (FP-3) and of the development of Plasmodium falciparum in vitro. Several compounds were equipotent to chloroquine as inhibitors of the 3D7 strain of P. falciparum and maintained potent activity against the chloroquine-resistant Dd2 parasite. These compounds serve as promising leads for the development of novel antimalarial agents.

  DOI：

  10.1021/jm501439w
• 作为产物：
  描述：

  (5S)-4-hydroxy-5-isopropyl-1-t-butoxycarbonylpyrrol-2(5H)-one 在 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 iheyanone
  参考文献：
  名称：

  高效合成dysidenin，dysidin和barbamide

  摘要：

  三种三氯亮氨酸衍生的海洋天然产物（dysidenin，dysidin和barbamide）的总合成以实用且高度非对映选择性的钌催化N-酰基氧杂唑烷酮的自由基氯烷基化为关键步骤。

  DOI：

  10.1002/asia.201100338

文献信息

• First Total Synthesis and Structure–Activity Relationship of Iheyamide A, an Antitrypanosomal Linear Peptide Isolated from a <i>Dapis</i> sp. Marine Cyanobacterium
  作者：Arihiro Iwasaki、Kazuya Teranuma、Naoaki Kurisawa、Yulia Rahmawati、Ghulam Jeelani、Tomoyoshi Nozaki、William H. Gerwick、Kiyotake Suenaga

  DOI：10.1021/acs.jnatprod.1c00792

  日期：2021.9.24

  Iheyamide A (1) is an antitrypanosomal linear peptide isolated from a Dapis sp. marine cyanobacterium by our group in 2020, and based on structure–activity relationships of its natural analogues, the C-terminal pyrrolinone moiety has been identified as the phamacophore for its antiparasitic activity. Further, we isolated this pyrrolinone moiety by itself as a new natural product from the marine cyanobacterium

  Iheyamide A ( 1 ) 是一种从Dapis sp. 中分离的抗锥虫线性肽。我们小组在 2020 年发现了海洋蓝藻，根据其天然类似物的结构-活性关系，C 端吡咯啉酮部分已被确定为具有抗寄生虫活性的药效团。此外，我们从海洋蓝藻中分离出这种吡咯啉酮部分作为一种新的天然产物，并将其命名为 iheyanone ( 2 )。正如预期的那样，iheyanone ( 2 ) 显示出抗锥虫活性，但其效力比 iheyamide A ( 1 )弱。为了阐明更详细的构效关系，我们完成了 iheyamide A ( 1 ) 和 iheyanone (2 ) 并评估了几种合成中间体的抗锥虫活性。结果，我们发现肽链越长，抗锥虫活性越强。由于 iheyamide A ( 1 ) 对罗得西亚布氏锥虫显示出选择性毒性，因此这些发现可为抗锥虫药物的设计提供指导。
• Total synthesis of malyngamide X and its 7′S-epi isomer
  作者：Suchada Suntornchashwej、Khanit Suwanborirux、Minoru Isobe

  DOI：10.1016/j.tet.2007.01.035

  日期：2007.4

  Stereoselective syntheses of malyngamide X (1) and its 7'(S)-epimer are described. A Lewis acid (Et2AlCl) mediated anti-aldol reaction was employed to generate the stereocenters C-7 and C-8. The route is convergent and provides a convenient access to the synthesis of structural variants of malyngamide X. Stereochemistry at C-7' in the molecules of natural and synthetic 1, and 7'(S)-epi 1 was confirmed by NMR chiral solvation experiments. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Gallinamide A Analogues as Potent Falcipain Inhibitors and Antimalarials
  作者：Trent Conroy、Jin T. Guo、Nabiha Elias、Katie M. Cergol、Jiri Gut、Jennifer Legac、Lubna Khatoon、Yang Liu、Sheena McGowan、Philip J. Rosenthal、Nicholas H. Hunt、Richard J. Payne

  DOI：10.1021/jm501439w

  日期：2014.12.26

  Analogues of the natural product gallinamide A were prepared to elucidate novel inhibitors of the falcipain cysteine proteases. Analogues exhibited potent inhibition of falcipain-2 (FP-2) and falcipain-3 (FP-3) and of the development of Plasmodium falciparum in vitro. Several compounds were equipotent to chloroquine as inhibitors of the 3D7 strain of P. falciparum and maintained potent activity against the chloroquine-resistant Dd2 parasite. These compounds serve as promising leads for the development of novel antimalarial agents.
• Efficient Total Synthesis of Dysidenin, Dysidin, and Barbamide
  作者：Elizabeth A. Ilardi、Armen Zakarian

  DOI：10.1002/asia.201100338

  日期：2011.9.5

  The total syntheses of three trichloroleucine‐derived marine natural products—dysidenin, dysidin, and barbamide—capitalized on a practical and highly diastereoselective ruthenium catalyzed radical chloroalkylation of N‐acyloxazolidinones as the key step.

  三种三氯亮氨酸衍生的海洋天然产物（dysidenin，dysidin和barbamide）的总合成以实用且高度非对映选择性的钌催化N-酰基氧杂唑烷酮的自由基氯烷基化为关键步骤。