nafuredin | 224427-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: nafuredin
• 英文别名: (1R,2R,5R,6S)-5-hydroxy-1-methyl-2-[(1E,3E,5R,7E,9E,11S)-5,7,11-trimethyltrideca-1,3,7,9-tetraenyl]-3,7-dioxabicyclo[4.1.0]heptan-4-one
• CAS: 224427-79-6
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: NMEGHQQRWKBPQO-IMNRXHEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  nafuredin 在 calcium carbonate 作用下， 以 甲醇 为溶剂， 反应 30.0h， 以93%的产率得到nafuredin-γ
  参考文献：
  名称：

  The total synthesis and biological evaluation of nafuredin-γ and its analogues

  摘要：

  Nafuredin (1) is converted to nafuredin-gamma (2) under mild basic conditions and both compounds exhibit the same inhibitory activity and selectivity against NADH-fumarate reductase (complex 1). The total synthesis of 2 was achieved by a convergent approach using Stille coupling. The structural elements required for inhibitory activity against NADH-fumarate reductase (complex I) were then investigated by evaluation of nafuredin-gamma (2) and its structural analogues. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.066
• 作为产物：
  描述：

  benzyl 4,6-O-benzylidene-α-D-glucopyranoside 在 palladium dihydroxide 、 palladium on activated charcoal 、 四(三苯基膦)钯 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 甲酸 、 ammonium heptamolybdate 、 三丁基膦 、 3 A molecular sieve 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 二异丁基氢化铝 、 二正丁基氧化锡 、 sodium cyanoborohydride 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 氟化氢吡啶 、 三乙胺 、 N,N-二异丙基乙胺 、 氯甲酸甲酯 、 lithium chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， -78.0~70.0 ℃ 、101.33 kPa 条件下， 反应 146.25h， 生成 nafuredin
  参考文献：
  名称：

  Total Synthesis of Nafuredin, a Selective NADH-fumarate Reductase Inhibitor

  摘要：

  Total synthesis of nafuredin, a selective NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach. The C1-C8 and C9-C18 segments were derived efficiently from D-glucose and (S)-(-)-2-methyl-1-butanol, respectively, coupled by stereoselective Julia olefination, and converted to nafuredin.

  DOI：

  10.1021/ol010089t

文献信息

• Absolute configuration of nafuredin, a new specific NADH-fumarate reductase inhibitor
  作者：Daisuke Takano、Tohru Nagamitsu、Hideaki Ui、Kazuro Shiomi、Yuuichi Yamaguchi、Rokuro Masuma、Isao Kuwajima、Satoshi Ōmura

  DOI：10.1016/s0040-4039(01)00355-0

  日期：2001.4

  Nafuredin, a new specific NADH-fumarate reductase inhibitor, was isolated from the culture broth of a fungal strain Aspergillus niger FT-0554. The stereoselective synthesis of three degradation products obtained by ozonolysis of nafuredin allowed elucidation of the absolute configuration of nafuredin.

  从真菌菌株黑曲霉FT-0554的培养液中分离出一种新的特异的NADH-富马酸酯还原酶抑制剂萘呋丁。立体分解合成的三种降解产物，其通过萘呋丁的臭氧分解得到，从而阐明了萘呋丁的绝对构型。
• Nafuredin, a Novel Inhibitor of NADH-fumarate Reductase, Produced by Aspergillus niger FT-0554.
  作者：HIDEAKI UI、KAZURO SHIOMI、YUUICHI YAMAGUCHI、ROKURO MASUMA、TOHRU NAGAMITSU、DAISUKE TAKANO、TOSHIAKI SUNAZUKA、MICHIO NAMIKOSHI、SATOSHI OMURA

  DOI：10.7164/antibiotics.54.234

  日期：——

  A novel compound, nafuredin, was isolated as an inhibitor of anaerobic electron transport (NADH-fumarate reductase). It was obtained from culture broth of Aspergillus niger FT-0554 isolated from a marine sponge. The structure was elucidated as an epoxy-δ-lactone with an attached methylated olefinic side chain on the basis of spectral analysis.
• The total synthesis and biological evaluation of nafuredin-γ and its analogues
  作者：Tohru Nagamitsu、Daisuke Takano、Miyuki Seki、Shiho Arima、Masaki Ohtawa、Kazuro Shiomi、Yoshihiro Harigaya、Satoshi Ōmura

  DOI：10.1016/j.tet.2008.06.066

  日期：2008.8

  Nafuredin (1) is converted to nafuredin-gamma (2) under mild basic conditions and both compounds exhibit the same inhibitory activity and selectivity against NADH-fumarate reductase (complex 1). The total synthesis of 2 was achieved by a convergent approach using Stille coupling. The structural elements required for inhibitory activity against NADH-fumarate reductase (complex I) were then investigated by evaluation of nafuredin-gamma (2) and its structural analogues. (C) 2008 Elsevier Ltd. All rights reserved.
• Total Synthesis of Nafuredin, a Selective NADH-fumarate Reductase Inhibitor
  作者：Daisuke Takano、Tohru Nagamitsu、Hideaki Ui、Kazuro Shiomi、Yuuichi Yamaguchi、Rokuro Masuma、Isao Kuwajima、Satoshi Ōmura

  DOI：10.1021/ol010089t

  日期：2001.7.1

  Total synthesis of nafuredin, a selective NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach. The C1-C8 and C9-C18 segments were derived efficiently from D-glucose and (S)-(-)-2-methyl-1-butanol, respectively, coupled by stereoselective Julia olefination, and converted to nafuredin.