Cerulenin | 68926-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: Cerulenin
• 英文别名: rel-(2S,3R)-3-((4E,7E)-Nona-4,7-dienoyl)oxirane-2-carboxamide；(2S,3R)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
• CAS: 68926-46-5
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: GVEZIHKRYBHEFX-UOQDJENHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Cerulenin 以86%的产率得到
  参考文献：
  名称：

  CLAREMON, DAVID A.;PHILLIPS, BRIAN T., TETRAHEDRON LETT., 29,(1988) N 18, 2155-2158

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-2,3-epoxy-4-hydroxy-trans,trans-7,10-dodecadienamide 在 dipyridine chromium trioxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以90%的产率得到Cerulenin
  参考文献：
  名称：

  Total syntheses of (.+-.)-cerulenin, (.+-.)-tetrahydrocerulenin and related compounds

  摘要：

  DOI：

  10.1021/jo00346a016

文献信息

• NOVEL COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME, AND METHODS OF USE FOR SAME
  申请人：Kuhajda Francis P.

  公开号：US20100029752A1

  公开（公告）日：2010-02-04

  A pharmaceutical composition containing a pharmaceutical diluent and a compound of formula II: wherein: R 8 ═H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, —C(O)R 4 , where R 4 is H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, optionally containing halogen atoms, or —OH, —OR 7 or —NR 7 , where R 7 is H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, optionally containing halogen atoms; R 9 =—OR 5 , —NR 5 , —NH—NH—R 5 where R 5 is H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, allyl, or alkylaryl, optionally containing halogen atoms; R 10 ═H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, or —CH 2 C(O)R 6 , where R 6 is OR 7 and NR 7 , where R 7 ═H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, allyl, or alkylaryl and can optionally contain halogen atoms. Also included in the invention are methods of using the pharmaceutical compositions and the chemical compounds used in the compositions.

  一种含有药物稀释剂和二式化合物的药物组合物，其中：R8═H、C1-C20烷基、环烷基、烯基、芳基、芳基烷基或烷基芳基，—C（O）R4，其中R4为H、C1-C20烷基、环烷基、烯基、芳基、芳基烷基或烷基芳基，可选地含有卤素原子，或—OH、—OR7或—NR7，其中R7为H、C1-C20烷基、环烷基、烯基、芳基、芳基烷基或烷基芳基，可选地含有卤素原子；R9=—OR5、—NR5、—NH—NH—R5，其中R5为H、C1-C20烷基、环烷基、烯基、芳基、芳基烷基、烯丙基或烷基芳基，可选地含有卤素原子；R10═H、C1-C20烷基、环烷基、烯基、芳基、芳基烷基或烷基芳基，或—CH2C（O）R6，其中R6为OR7和NR7，其中R7═H、C1-C20烷基、环烷基、烯基、芳基、芳基烷基、烯丙基或烷基芳基，可选地含有卤素原子。发明还包括使用药物组合物和组合物中使用的化学化合物的方法。
• Methods for efficient production of polyunsaturated fatty acids (PUFA) in Rhodosporidium and Rhodotorula species
  申请人：Temasek Life Sciences Laboratory Limited

  公开号：US10081821B2

  公开（公告）日：2018-09-25

  The present invention relates to the field of fungal biotechnology, more particularly to genetic engineering methods for the production of polyunsaturated fatty acids (PUFA) in fungal hosts selected from Rhodosporidium and Rhodotorula genera. The present invention further relates to a modified fungal host cell having reduced native aldehyde dehydrogenase (ALD 1) enzyme activity, and methods for producing omega-3 and omega-6 fatty acids and triacylglycerides, by growing said fungal host cell under suitable conditions.

  本发明涉及真菌生物技术领域，更具体地说，涉及在选自 Rhodosporidium 和 Rhodotorula 属的真菌宿主中生产多不饱和脂肪酸 (PUFA) 的基因工程方法。本发明进一步涉及一种具有降低的原生醛脱氢酶（ALD 1）酶活性的改良真菌宿主细胞，以及通过在适当条件下培养所述真菌宿主细胞生产欧米伽-3 和欧米伽-6 脂肪酸及三酰基甘油酯的方法。
• Novel compounds, pharmaceutical compositions containing same, and methods of use for same
  申请人：Kuhadja P. Francis

  公开号：US20060241177A1

  公开（公告）日：2006-10-26

  Pharmaceutical composition comprising a pharmaceutical diluent and a compound of formula IX: R 29 ═H, or C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, ═CHR 31 , —C(O)OR 31 , —C(O)R 31 , —CH 2 C(O)OR 31 , CH 2 C(O)NHR 31 , where R 31 is H or C 1 -C 10 alkyl, cycloalkyl, or alkenyl; R 30 ═C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl; X 5 ═—OR 32 , or NHR 32 , Where R 32 is H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, the R 32 group optionally containing a carbonyl group, a carboxyl group, a carboxyamide group, an alcohol group, or an ether group, the R 32 group further optionally containing one or more halogen atoms; with the proviso that when R 29 is ═CH 2 , then X 5 is not OH. Also disclosed are compounds within the scope of the formula IX, as well as uses of the pharmaceutical compositions for weight loss, anti-microbial and anti-cancer applications, inhibition of fatty acid synthase and neuropeptide-Y, and the stimulation of the activity of carnitine palmitoyl transferase-1.

  药物组合物，包括药物稀释剂和式 IX 的化合物：R 29 ═H，或 C 1 -C 20 烷基、环烷基、烯基、芳基、芳烷基或烷基芳基，═CHR 31 、-C(O)OR 31 、-C(O)R 31 , -CH 2 C(O)OR 31 , CH 2 C(O)NHR 31 其中 R 31 是 H 或 C 1 -C 10 烷基、环烷基或烯基； R 30 ═C 1 -C 20 烷基、环烷基、烯基、芳基、芳烷基或烷基芳基； X 5 ═-OR 32 或 NHR 32 其中 R 32 是 H、C 1 -C 20 烷基、环烷基、烯基、芳基、芳烷基或烷基芳基，R 32 基团可选择含有羰基、羧基、羧酰胺基、醇基或醚基，R 32 基团还可选择含有一个或多个卤素原子；但当 R 29 是 ═CH 2 则 X 5 不是 OH。还公开了式 IX 范围内的化合物，以及药物组合物在减肥、抗微生物和抗癌、抑制脂肪酸合酶和神经肽-Y 以及刺激肉碱棕榈酰转移酶-1 活性方面的用途。
• A convergent asymmetric synthesis of γ-butenolides
  作者：Marc Renard、Léon A. Ghosez

  DOI：10.1016/s0040-4020(01)00078-3

  日期：2001.3

  The addition of aldehydes to the new enantiomerically pure lithiated sulfoxide-orthoester 13 yielded gamma -butenolides of high enantiomeric purities after elimination of phenylsulfinic acid. The cyclocondensation with ketones was less stereoselective. This new asymmetric synthesis of gamma -butenolides has been applied to a convergent preparation of the antifungal antibiotic (+)-cerulenin. (C) 2001 Elsevier Science Ltd. All rights reserved.
• CLAREMON, DAVID A.;PHILLIPS, BRIAN T., TETRAHEDRON LETT., 29,(1988) N 18, 2155-2158
  作者：CLAREMON, DAVID A.、PHILLIPS, BRIAN T.

  DOI：——

  日期：——