(2E)-3-(6-Quinolinyl)-2-propenal | 130520-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (2E)-3-(6-Quinolinyl)-2-propenal
• 英文别名: (E)-3-(6-quinolinyl)-2-propenal；3t-[6]quinolyl-acrylaldehyde；3t-[6]Chinolyl-acrylaldehyd；3-(6-Quinolinyl)-2-propenal；(E)-3-quinolin-6-ylprop-2-enal
• CAS: 130520-72-8
• 化学式: C₁₂H₉NO
• 分子量: 183.21
• InChiKey: MZXKEWFFQIBAHQ-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-3-(6-Quinolinyl)-2-propenal 在 三乙基硅烷 、 碳酸氢钠 、 三氟乙酸 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 [(1S,2R,5S,7R,8R,9R,11R,12E,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-5-fluoro-12-hydroxyimino-1,5,7,9,11,13-hexamethyl-4,6,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-9-yl] N-[(E)-3-quinolin-6-ylprop-2-enyl]carbamate
  参考文献：
  名称：

  Synthesis and antibacterial activity of C2-fluoro, C6-carbamate ketolides, and their C9-oximes

  摘要：

  Novel C6-carbamate ketolides with C2-fluorination and C9-oximation have been synthesized. The best compounds in this series displayed MIC values of 0.03-0.12 mug/mL against streptococci containing erm and mef resistance determinants and 2-4 mug/mL against Haemophilus influenzae. Several compounds also showed measurable activity against erm(B)-containing enterococci with MIC values of 2-8 mug/mL. In vivo activity was adversely affected by fluorination, possibly as a result of increased serum protein binding. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.067
• 作为产物：
  描述：

  喹啉-6-甲醛 、 乙醛 在 sodium hydroxide 、 水 、 苯 作用下， 生成 (2E)-3-(6-Quinolinyl)-2-propenal
  参考文献：
  名称：

  Waley, Journal of the Chemical Society, 1949, p. 2008,2010

  摘要：

  DOI：

文献信息

• 6-O-carbamate-11,12-lacto-ketolide antimicrobials
  申请人：——

  公开号：US20030125267A1

  公开（公告）日：2003-07-03

  6-O-Carbamate-11,12-lacto-ketolide antimicrobials of the formula: 1 wherein R 1 , R 2 , R 3 R 7 , and R 8 are as described herein and in which the substituents have the meaning indicated in the description. These compounds are useful as antibacterial agents.

  其中R1、R2、R3、R7和R8如本文所述，并且取代基具有描述中指示的含义。这些化合物可用作抗菌剂。
• 6-O-acyl ketolide antibacterials
  申请人：——

  公开号：US20030220272A1

  公开（公告）日：2003-11-27

  6-O-Acyl ketolide antibacterials of the formula: 1 wherein R 1 , R 2 , R 3 , R 4 , W, X, X′, Y, and Y′ are as described herein and in which the substituents have the meaning indicated in the description. These compounds are useful as antibacterial agents.

  其中R1、R2、R3、R4、W、X、X'、Y和Y'如本文所述，并且其中取代基具有描述中指示的含义。这些化合物可用作抗菌剂。
• 6-0-carbamoyl ketolide antibacterials
  申请人：——

  公开号：US20020115620A1

  公开（公告）日：2002-08-22

  6-O-Carbamoyl ketolide antibacterials of the formula: 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X, X′, Y, and Y′ are as described herein and in which the substituents have the meaning indicated in the description. These compounds are useful as antibacterial agents.

  其中R1、R2、R3、R4、R5、R6、X、X'、Y和Y'如本文所述，并且其中取代基具有描述中指示的含义。这些化合物可用作抗菌剂。
• ANTICANCER 1,3-DIOXANE-4,6-DIONE DERIVATIVES AND METHOD OF COMBINATORIAL SYNTHESIS THEREOF
  申请人：National Guard Health Affairs

  公开号：US20200290975A1

  公开（公告）日：2020-09-17

  Compounds, methods of synthesis, and methods of cancer treatment by arylidene-1,3-dioxane-4,6-diones. A Meldrum's acid-based chemistry and hybrid solid-liquid method. The method includes protection of ketone and aldehyde components and simultaneous immobilization on the solid phase, introduction of substituents, grafts and derivatives compatible with the protection, detachment and restoration of active carbonyl reactivity, reaction of ketone library with malonate, reacting of the products with the aldehyde library in liquid phase and separation of the products by preparative HPLC.

  芳基亚甲基-1,3-二氧杂环己-4,6-二酮的化合物、合成方法和癌症治疗方法。基于梅尔德鲁姆酸的化学和混合固-液方法。该方法包括对酮和醛组分进行保护并同时固相固定，引入适用于保护的取代基、嫁接和衍生物，分离和恢复活性羰基反应性，将酮库与马隆酸酯反应，将产物与液相中的醛库反应，通过制备性高效液相色谱法分离产物。
• Synthesis and antibacterial activity of 6-O-heteroarylcarbamoyl-11,12-lactoketolides
  作者：Eugene B. Grant、Deodialsingh Guiadeen、Darren Abbanat、Barbara D. Foleno、Karen Bush、Mark J. Macielag

  DOI：10.1016/j.bmcl.2005.12.097

  日期：2006.4

  12-lactoketolides, with activity against macrolide-resistant streptococci, are described. Structurally, these macrolide antibiotics are characterized by a heteroaryl side chain attached to the macrolactone core through a carbamate linkage at the C6 position, as well as 11,12-gamma-lactone and 3-keto functionalities. The synthesis and antibacterial activity of this new series of ketolides are discussed.

  描述了一系列新的红霉素A衍生物，即6-O-杂芳基氨基甲酰基-11,12-乳酮醇内酯，对大环内酯类耐药链球菌具有活性。从结构上讲，这些大环内酯类抗生素的特征是杂芳基侧链通过C6位置的氨基甲酸酯键连接到大内酯核心上，以及11,12-γ-内酯和3-酮官能团。讨论了该新系列酮醇化物的合成和抗菌活性。