2-chloro-4-(N,N-diethylthiocarbamoyl)quinoline | 135323-94-3

• 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: 2-chloro-4-(N,N-diethylthiocarbamoyl)quinoline
• 英文别名: 2-chloro-N,N-diethylquinoline-4-carboxamide；N,N-diethyl 2-chloroquinoline-4-carboxamide；2-chloro-quinoline-4-carboxylic acid diethylamide；2-Chlor-chinolin-4-carbonsaeure-diaethylamid
• CAS: 135323-94-3
• 化学式: C₁₄H₁₅ClN₂O
• mdl: MFCD00444355
• 分子量: 262.739
• InChiKey: HOLOVODXKJDYQV-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  434.1±30.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-4-(N,N-diethylthiocarbamoyl)quinoline 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 diethylamide of 1,2,4-triazolo[4,3-a]quinoline-9-carboxylic acid
  参考文献：
  名称：

  取代的2-肼基-和2-（Β-酰基肼基）-辛二酸酰胺的合成及其环化成1,2,4-三唑并[4,3-a]喹啉-9-羧酸酰胺

  摘要：

  DOI：

  10.1007/bf00480836
• 作为产物：
  描述：

  2-羟基喹啉-4-羧酸 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 2-chloro-4-(N,N-diethylthiocarbamoyl)quinoline
  参考文献：
  名称：

  Further Studies on the Interaction of the 5-Hydroxytryptamine₃ (5-HT₃) Receptor with Arylpiperazine Ligands. Development of a New 5-HT₃ Receptor Ligand Showing Potent Acetylcholinesterase Inhibitory Properties

  摘要：

  Novel arylpiperazine derivatives bearing lipophilic probes were designed, synthesized, and evaluated for their potential ability to interact with the 5-hydroxytryptamine(3) (5-HT3) receptor. Most of the new compounds show subnanomolar 5-HT3 receptor affinity. Ester 6bc showing a picomolar K-i value is one of the most potent 5-HT3 receptor ligands so far synthesized. The structure-affinity relationship study suggests the existence of a certain degree of conformational freedom of the amino acid residues interacting with the substituents in positions 3 and 4 of the quipazine quinoline nucleus. Thus, the tacrine-related heterobivalent ligand 6o was designed in an attempt to capitalize on the evidence of such a steric tolerance. Compound 6o shows a nanomolar potency for both the 5-HT3 receptor and the human AChE and represents the first example of a rationally designed high-affinity 5-HT3 receptor ligand showing nanomolar AChE inhibitory activity. Finally, the computational analysis performed on compound 6o allowed the rationalization of the structure-energy determinants for AChE versus BuChE selectivity and revealed the existence of a subsite at the boundary of the 5-HT3 receptor extracellular domain, which could represent a "peripheral" site similar to that evidenced in the AChE gorge.

  DOI：

  10.1021/jm0493461

文献信息

• Reactions of thionyl chloride with C-methyl heterocycles. Part 2. The formation of [1,2]dithiolo[3,4-c]quinolin-1-ones and bis[dichloro(4-quinolyl)methyl]trisulphanes from 4-methylquinolines
  作者：Adnan H. M. Al-Shaar、David J. Lythgoe、Ian McClenaghan、Christopher A. Ramsden

  DOI：10.1039/p19880003025

  日期：——

  4-Methylquinolines (1) react with hot thionyl chloride to give either 4-chloro[1,2]dithiolo[3,4-c]quinolin-1-ones (2) or bis[dichloro(4-quinolyl)methyl]trisulphanes (18). The mode of formation of these products is discussed and their reactions with various reagents are described.

  4-甲基喹啉（1）与热的亚硫酰氯反应，生成4-氯[1,2]二硫代[3,4- c ]喹啉-1-酮（2）或双[二氯（4-喹啉基）甲基]三硫氰酸根。 （18）。讨论了这些产物的形成方式，并描述了它们与各种试剂的反应。
• Synthesis and antiinflammatory and analgesic activities of quinolino[2,1-b]quinazoline derivatives
  作者：A. I. Mikhalev、M. E. Konshin、O. A. Yanborisova、A. S. Zaks、V. V. Yushkov

  DOI：10.1007/bf00768982

  日期：1991.10

  694697 (1988). 3. I.F. Izmerov, I. V. Sanotskii, and K. K. Sidorov, Parameters of Toxicometry of Industrial Poisons in the Case of Single Exposure [in Russian], Moscow (1977). 4. Kh. M. Nasyrov, Synthesis and Preclinical investigation of Novel Biologically Active Compounds [in Russian], Ufa (1988), pp. 49-54. 5. G.A. Tolstikov, U. M. Dzhemilev, and A. Sh. Yukhanova, Zh. Obshch. Khim., 46, No. 4, 917-923

  一世。LA Baltina、RM Kondratenko 和 GA Tolstikov，Zh。奥布希。Khim., 54, No. ii, 2573-2579 (1984)。2. LA Baltina, VA Davydova, IG Chikaeva, et ai., Khim.-farm。Zh., No. 6, 694697 (1988)。3. IF Izmerov、IV Sanotskii 和 KK Sidorov，《单一暴露情况下工业毒物的毒理学参数》[俄语]，莫斯科（1977 年）。4. 小时。M. Nasyrov，新型生物活性化合物的合成和临床前研究 [俄文]，Ufa (1988)，第 49-54 页。5. GA Tolstikov、UM Dzhemilev 和 A. Sh. 尤哈诺娃，Z. 奥布希。Khim., 46, No. 4, 917-923 (1976)。6. GA Tolstikov、LA
• Untersuchungen über den Zusammenhang von chemischer Konstitution und anästhesierender Wirkung bei 2-Alkoxy-chinolin-Derivaten
  作者：Hans Wojahn

  DOI：10.1002/ardp.19362740202

  日期：——
• DE537104
  申请人：——

  公开号：——

  公开（公告）日：——
• Dehalogenation and Barbier-Type Hydroxyalkylation of π-Deficient Haloheterocycles Using Indium
  作者：Osamu Sugimoto、Ken-ichi Tanji、Eri Fukuda、Yukiko Takahashi、Natsumi Hirasawa

  DOI：10.3987/com-08-s(f)95

  日期：——

  The reaction of pi-deficient haloheterocycles with indium metal in water gave corresponding dehalogenated heterocycles. The use of diluted hydrochloric acid instead of water accelerated the reductive reactivity of indium metal. Furthermore, Barbier-type additions proceeded by reactions of alpha-iodoheterocycles with indium in the presence of pivalaldehyde.