6-ethyl-2-methylsulfanyl-9-oxo-6,9-dihydro-thiazolo[5,4-f]quinoline-8-carboxylic acid ethyl ester | 34976-36-8

• 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: 6-ethyl-2-methylsulfanyl-9-oxo-6,9-dihydro-thiazolo[5,4-f]quinoline-8-carboxylic acid ethyl ester
• 英文别名: Ethyl 6-ethyl-2-methylsulfanyl-9-oxo-[1,3]thiazolo[5,4-f]quinoline-8-carboxylate
• CAS: 34976-36-8
• 化学式: C₁₆H₁₆N₂O₃S₂
• 分子量: 348.447
• InChiKey: NTXANHRNNGNJCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-ethyl-2-methylsulfanyl-9-oxo-6,9-dihydro-thiazolo[5,4-f]quinoline-8-carboxylic acid ethyl ester 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 6-ethyl-2-methylsulfanyl-9-oxo-6,9-dihydro-thiazolo[5,4-f]quinoline-8-carboxylic acid
  参考文献：
  名称：

  合成化学治疗剂。I.2-取代的噻唑并（5，4-f）喹啉衍生物的合成。

  摘要：

  通过使用6-氨基苯并噻唑作为起始材料，经过一系列步骤，例如与二乙基乙氧亚甲基丙二酸二乙酯缩合、Gould-Jacobs反应、N-烷基化和水解，制备了一系列2-取代的6-乙基-6,9-二氢-9-氧代噻唑并[5,4-f]喹啉-8-羧酸。这些化合物在体外进行了抗菌活性评估。2-氯代衍生物(10d)显示出与萘啶酸几乎相同的活性。

  DOI：

  10.1248/cpb.24.130
• 作为产物：
  描述：

  2,2,2-trifluoro-N-(2-methylsulfanyl-benzothiazol-6-yl)-acetamide 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 6-ethyl-2-methylsulfanyl-9-oxo-6,9-dihydro-thiazolo[5,4-f]quinoline-8-carboxylic acid ethyl ester
  参考文献：
  名称：

  合成化学治疗剂。I.2-取代的噻唑并（5，4-f）喹啉衍生物的合成。

  摘要：

  通过使用6-氨基苯并噻唑作为起始材料，经过一系列步骤，例如与二乙基乙氧亚甲基丙二酸二乙酯缩合、Gould-Jacobs反应、N-烷基化和水解，制备了一系列2-取代的6-乙基-6,9-二氢-9-氧代噻唑并[5,4-f]喹啉-8-羧酸。这些化合物在体外进行了抗菌活性评估。2-氯代衍生物(10d)显示出与萘啶酸几乎相同的活性。

  DOI：

  10.1248/cpb.24.130

文献信息

• Synthetic chemotherapeutic agents. IV. Synthesis of 3-substituted thiazolo(5,4-f)quinoline derivatives.
  作者：NORIO SUZUKI、SHIZUO KADOYA、RENZO DOHMORI

  DOI：10.1248/cpb.24.1050

  日期：——

  A method of synthesizing for 3, 6-disubstituted 2, 9-dioxo-2, 3, 6, 9-tetrahydrothiazolo-[5, 4-f] quinoline-8-carboxylic acids via the thiazolium salts was studied and proved to be practical. The reactions of the thiazolium salt with various nucleophilic reagents afforded several new derivatives. Gould-Jacobs reaction of the benzothiazole-2-ones and benzothiazole-2-thione derivatives were also carried out.

  研究并证明了通过噻唰盐合成3,6-二取代-2,9-二氧-2,3,6,9-四氢噻唑并[5,4-f]喹啉-8-羧酸的方法是切实可行的。噻唑盐与各种亲核试剂的反应得到了几种新衍生物。还进行了苯并噻唑-2-酮和苯并噻唑-2-硫酮衍生物的Gould-Jacobs反应。
• Synthetic chemotherapeutic agents. III. Synthesis of 3-substituted thiazolo(5,4-f)quinoline derivatives. (1).
  作者：SHIZUO KADOYA、NORIO SUZUKI、ISAO TAKAMURA、RENZO DOHMORI

  DOI：10.1248/cpb.24.147

  日期：——

  For the search of the more active antimicrobial compounds than the 2, 6-disubstituted derivatives, 3, 6-disubstituted 2, 3, 6, 9-tetrahydro-2, 9-dioxothiazolo [5, 4-f] quinoline-8-carboxylic acid (1, 3, 7, 8, 11, 20, 21, and 22) were synthesized from the 2-oxo-6-substituted thiazolo [5, 4-f] quinoline derivatives (2, 17, or 18). Thermal rearrangement of the 2-methylthio derivative (23) gave the 2-thioxo-3-methyl derivative (24), which was converted into the 2-oxo-3-methyl derivative (26) by reaction with mercuric acetate. The 2-ethoxy derivative (27) was also thermally rearranged to give the 2-oxo-3-ethyl derivative (8b). The 3, 6-disubstituted compounds obtained in this work showed the stronger activities against gram-negative and gram-positive bacteria in vitro than nalidixic acid and the 2, 6-disubstituted derivatives prepared in the previous work. 6-Ethyl-2, 3, 6, 9-tetrahydro-3-methyl-9-oxothiazolo [5, 4-f] quinoline-8-carboxylic acid (8a) exhibited the strongest activities among these compounds against many gram-negative bacteria including E. coli resistant to nalidixic acid and Ps. aeruginosa, and against some gram-positive bacteria.

  为了寻找比2,6-取代衍生物更活跃的抗微生物化合物，合成了3,6-取代的2,3,6,9-四氢-2,9-二氧噻唑[5,4-f]喹啉-8-羧酸（1、3、7、8、11、20、21和22），这些化合物是从2-氧-6-取代噻唑[5,4-f]喹啉衍生物（2、17或18）合成的。2-甲基硫衍生物（23）的热重排反应生成了2-硫氧-3-甲基衍生物（24），该衍生物与醋酸汞反应转化为2-氧-3-甲基衍生物（26）。2-醇乙氧基衍生物（27）也经过热重排生成了2-氧-3-乙基衍生物（8b）。本研究中获得的3,6-取代化合物在体外对革兰阴性菌和革兰阳性菌的活性较之前工作中制备的氟喹诺酮酸和2,6-取代衍生物更强。6-乙基-2,3,6,9-四氢-3-甲基-9-氧噻唑[5,4-f]喹啉-8-羧酸（8a）在这些化合物中对包括对氟喹诺酮酸耐药的大肠杆菌和铜绿假单胞菌在内的多种革兰阴性菌，以及对一些革兰阳性菌表现出最强的活性。
• Synthetic chemotherapentic agents. II. Synthesis of 2-substituted thiazolo(5,4-f)quinoline derivatives. (2).
  作者：SHIZUO KADOYA、ISAO TAKAMURA、NORIO SUZUKI、RENZO DOHMORI

  DOI：10.1248/cpb.24.136

  日期：——

  In order to search for new antimicrobial agents, a number of 2-substituted 6-ethyl-6, 9-dihydro-9-oxothiazolo [5, 4-f] quinoline-8-carboxylic acids were prepared. Nucleophilic reactions of the 2-methylsulfonyl derivative (6 or 13) gave the 2-alkoxy (12), 2-cyano (14), 2-amino (15 and 19) and other derivatives. By using the 2-cyano compound (3 or 14), various derivatives were also prepared, e.g., the 2-amidine (24h), 2-imido-ether (27), 2-carbamoyl (26 and 30) and other derivatives. Formation of the 9-ethoxy compound (33) by ethylation of the 8-decarboxylated compound (34) was also described. These compounds obtained were tested for their antimicrobial activities in vitro. The 2-cyano (14), 2-carbamoyl (26), 2-diethylaminoethylcarbamoyl (30f) and some other derivatives showed the stronger activities than nalidixic acid. The most active compound, 30f, exhibited the activities against Escherichia coli resistant to nalidixic acid, but had no activity against Ps. aeruginosa.

  为了寻找新的抗菌药物，制备了多种2-取代的6-乙基-6, 9-二氢-9-氧代噻唑并[5, 4-f]喹啉-8-羧酸。 2-甲基磺酰基衍生物（6或13）的亲核反应得到2-烷氧基（12）、2-氰基（14）、2-氨基（15和19）和其他衍生物。利用2-氰基化合物（3或14）还可以制备各种衍生物，例如2-脒（24h）、2-亚氨基醚（27）、2-氨基甲酰基（26和30）等衍生物。还描述了通过8-脱羧化合物(34)的乙基化形成9-乙氧基化合物(33)。测试了获得的这些化合物的体外抗菌活性。 2-氰基(14)、2-氨基甲酰基(26)、2-二乙氨基乙基氨基甲酰基(30f)等衍生物的活性比萘啶酸更强。最活跃的化合物30f表现出针对耐萘啶酸的大肠杆菌的活性，但对Ps没有活性。铜绿假单胞菌。
• KADOYA S.; SUZUKI N.; TAKAMURA I.; DOHMORI R., CHEM. AND PHARM. BULL. <CPBT-AL>, 1976, 24, NO 1, 147-155
  作者：KADOYA S.、 SUZUKI N.、 TAKAMURA I.、 DOHMORI R.

  DOI：——

  日期：——