3-氧代-N-(2-氧代四氢呋喃-3-基)十二碳酰胺 | 152833-54-0

• 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
• 中文名称: 3-氧代-N-(2-氧代四氢呋喃-3-基)十二碳酰胺
• 英文名称: 3OC12-HSL
• 英文别名: N-(3-Oxododecanoyl)homoserine lactone；3-oxo-N-(2-oxooxolan-3-yl)dodecanamide
• CAS: 152833-54-0
• 化学式: C₁₆H₂₇NO₄
• 分子量: 297.395
• InChiKey: PHSRRHGYXQCRPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  α-氨基-γ-丁内酯氢溴酸盐 、 2,2-dimethyl-5-(1-oxodecyl)-1,3-dioxane-4,6-dione 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 3-氧代-N-(2-氧代四氢呋喃-3-基)十二碳酰胺
  参考文献：
  名称：

  Absolute Configuration and Antimicrobial Activity of Acylhomoserine Lactones

  摘要：

  (S)-N-Heptanoylhomoserine lactone is an uncommon acyl odd-chain natural product employed by many Gram-negative bacteria as a signaling substance in chemical communication mechanisms known as quorum sensing. The absolute configuration determination of the metabolite produced by the phytopathogen Pantoea ananatis Serrano is reported herein. As with all other substances of this class, the lactone moiety possesses S configuration, corroborating the hypothesis that it shares the same biosynthetic pathway as the (S)-N-hexanoylhomoserine lactone and also that some LuxI homologues can accept both hexanoyl- and heptanoyl-ACP as precursors. Evaluation of the antimicrobial activity of enantiomeric acylhomoserine lactones against three Gram-positive bacteria (Bacillus cereus, B. subtilis, and Staphylococcus aureus) revealed important features between absolute configuration and antimicrobial activity. The N-heptanoylhomoserine lactone was considerably less active than the 3-oxo derivatives. Surprisingly, non-natural (R)-N-(3-oxo-octanoyl)homoserine lactone was as active as the S enantiomer against B. cereus, while the synthetic racemic product was less active than either enantiomer.

  DOI：

  10.1021/np800127b

文献信息

• [EN] ANDROGRAPHOLIDE DERIVATIVES AND USE THEREOF IN MANUFACTURE OF MEDICAMENTS<br/>[FR] DÉRIVÉS D'ANDROGRAPHOLIDE ET LEUR UTILISATION POUR LA FABRICATION DE MÉDICAMENTS
  申请人：PANORAMA RES INC

  公开号：WO2009018780A1

  公开（公告）日：2009-02-12

  The present invention relates to an andrographolide derivative of the formula (I), wherein R1, R2 and R3 are same or different substituents selected from hydrogen, substituted or unsubstituted organic acid radicals, inorganic acid radicals, alkyl, aryl or heteroaryl, and at least one of R1, R2 and R3 is R-lipoic acid, S-lipoic acid or a mixture thereof, or corresponding dihydrolipoic acids thereof, or N-acetylcysteine radical. The derivative has good antitumor effect, can induce apoptosis of tumor cells, can directly kill Gram-positive bacteria (staphylococcus aureus) and drug resistance bacteria (MRSA5676 and MRSA5677), can inhibit the QS-system of Gram-negative bacteria (Pseudomonas aeruginosa), can inhibit and destroy the formation of biofilm of Pseudomonas aeruginosa; and exhibits significant hypoglycemic effect, so that it can be used in manufacture of medicaments for treatment of cancers, inflammation, diabetes, and bacterial and viral infections.

  本发明涉及一种公式（I）的andrographolide衍生物，其中R1、R2和R3是相同或不同的取代基，选自氢、取代或未取代的有机酸基团、无机酸基团、烷基、芳基或杂环芳基，且R1、R2和R3中至少有一个是R-硫辛酸、S-硫辛酸或二者的混合物，或相应的二氢硫辛酸，或N-乙酰半胱氨酸基团。该衍生物具有良好的抗肿瘤效果，可以诱导肿瘤细胞凋亡，可以直接杀死革兰氏阳性细菌（金黄色葡萄球菌）和耐药细菌（MRSA5676和MRSA5677），可以抑制革兰氏阴性细菌（铜绿假单胞菌）的QS系统，可以抑制和破坏铜绿假单胞菌生物膜的形成；并且具有显著的降糖作用，因此可以用于制造用于治疗癌症、炎症、糖尿病以及细菌和病毒感染的药物。
• ANDROGRAPHOLIDE DERIVATIVES AND USE THEREOF IN MANUFACTURE OF MEDICAMENTS
  申请人：Wang Yuqiang

  公开号：US20110077295A1

  公开（公告）日：2011-03-31

  The present invention relates to an andrographolide derivative of the formula (I), wherein R 1 , R 2 and R 3 are same or different substituents selected from hydrogen, substituted or unsubstituted organic acid radicals, inorganic acid radicals, alkyl, aryl or heteroaryl, and at least one of R 1 , R 2 and R 3 is R-lipoic acid, S-lipoic acid or a mixture thereof, or corresponding dihydrolipoic acids thereof, or N-acetylcysteine radical. The derivative has good antitumor effect, can induce apoptosis of tumor cells, can directly kill Gram-positive bacteria ( staphylococcus aureus ) and drug resistance bacteria (MRSA5676 and MRSA5677), can inhibit the QS-system of Gram-negative bacteria ( Pseudomonas aeruginosa ), can inhibit and destroy the formation of biofilm of Pseudomonas aeruginosa; and exhibits significant hypoglycemic effect, so that it can be used in manufacture of medicaments for treatment of cancers, inflammation, diabetes, and bacterial and viral infections.

  本发明涉及一种公式（I）的andrographolide衍生物，其中R1、R2和R3是相同或不同的取代基，所选取代基包括氢、取代或未取代的有机酸基团、无机酸基团、烷基、芳基或杂环基，且R1、R2和R3中至少有一个是R-硫辛酸、S-硫辛酸或其混合物，或相应的二氢硫辛酸，或N-乙酰半胱氨酸基团。该衍生物具有良好的抗肿瘤效果，可以诱导肿瘤细胞凋亡，可以直接杀死革兰阳性细菌（金黄色葡萄球菌）和耐药细菌（MRSA5676和MRSA5677），可以抑制革兰阴性细菌（铜绿假单胞菌）的QS系统，可以抑制和破坏铜绿假单胞菌的生物膜形成；并具有显著的降血糖作用，因此可以用于制造治疗癌症、炎症、糖尿病和细菌和病毒感染的药物。
• COMPOUNDS AND METHODS FOR MODULATING COMMUNICATION AND VIRULENCE IN QUORUM SENSING BACTERIA
  申请人：BLACKWELL Helen E.

  公开号：US20100305182A1

  公开（公告）日：2010-12-02

  The present invention provides compositions and methods for modulating the communication and virulence of quorum sensing bacteria. In various exemplary embodiments, the invention provides a combinatorial library of quorum sensing compounds including synthetic analogs of naturally occurring and non-naturally occurring acyl-homoserine lactone (AHL) analogs, and methods of synthesizing and using these compounds.

  本发明提供了调节群体感应细菌的通讯和毒力的组合物和方法。在各种示例实施方案中，本发明提供了一种群体感应化合物的组合库，包括天然存在和非天然存在的酰基-同型半乳糖内酯（AHL）类似物的合成类似物，以及这些化合物的合成和使用方法。
• Use of acyl-homoserine lactone derivatives as anti-thrombotic agents
  申请人：The University of Toledo

  公开号：US10195177B2

  公开（公告）日：2019-02-05

  Uses of acyl-homoserine lactone compounds are described. In particular, uses of acyl-homoserine lactone compounds as anti-thrombotic agents, to inhibit platelets from becoming hypersensitive, and/or to prevent thrombosis, are described.

  描述了酰基高丝氨酸内酯化合物的用途。特别是描述了酰基高丝氨酸内酯化合物作为抗血栓药、抑制血小板变得超敏和/或防止血栓形成的用途。
• Methods of treating or preventing an infectious disease using an immunogenic conjugate of a gram-negative bacterial autoinducer molecule or antibodies that immunospecifically bind a gram-negative bacterial autoinducer molecule
  申请人：Kende S. Andrew

  公开号：US20070231839A1

  公开（公告）日：2007-10-04

  The present invention relates to an immunogenic conjugate comprising a carrier molecule coupled to an autoinducer of a Gram negative bacteria The immunogenic conjugate, when combined with a pharmaceutically acceptable carrier, forms a suitable vaccine for mammals to prevent infection by the Gram negative bacteria The immunogenic conjugate is also used to raise and subsequently isolate antibodies or binding portions thereof which are capable of recognizing and binding to the autoinducer. The antibodies or binding portions thereof are utilized in a method of treating infections, a method of inhibiting autoinducer activity, and in diagnostic assays which detect the presence of autoinducers or autoinducer antagonists in fluid or tissue samples. TABLE OF CONTENTS Page 1. FIELD OF THE INVENTION 1 2. BACKGROUND OF THE INVENTION 1 3. SUMMARY OF THE INVENTION 4 4. BRIEF DESCRIPTION OF THE DRAWINGS 7 5. DETAILED DESCRIPTION OF THE INVENTION 7 5.1 Isolation and Synthesis of Homoserine Lactones 7 5.2 Bacterial Autoinducer Conjugation to a Carrier 17 5.3 Generation of Antibodies to BAI Immunogenic conjugates 19 5.4 Therapeutic Uses of Immunogenic conjugates 22 or Antibodies Thereto 5.4.1 Administration and Formulation 22 5.4.2 Effective Dose 25 5.5 Diagnostic Methods 27 6. EXAMPLE: SYNTHESIS 32 Preparation of Compound C 32 Preparation of Compound D 32 Preparation of Compound 5 32 Preparation of Compound 6 33 Preparation of Compound 7 33 Preparation of Compound 8 33 Preparation of Compound 10 34 Preparation of Compound 11 34 Preparation of Compound 13 35 Preparation of Compound 12 35 Preparation of Compound 14 35 Preparation of Compound 15 36 Preparation of Compound 17 36 Preparation of Compound 21 37 Preparation of Compound 22 37 Preparation of Compound 24 38 Preparation of Compound 25 38 Preparation of Compound 27 38 Preparation of Compound 29 39 7. EXAMPLE: PRODUCTION OF BAI ANTIBODIES 39 7.1 PAI'S Role In Virulence 39 7.2 Anti-PAI Polyclonal Antibodies 40 7.3 Neutralization of PAI With Antibodies 40