2-phenylthiazolidine-4-carboxylic acid ethyl ester

• 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
• 英文名称: 2-phenylthiazolidine-4-carboxylic acid ethyl ester
• 英文别名: ethyl 2-phenylthiazolidine-4-carboxylate；Ethyl 2-phenyl-1,3-thiazolidine-4-carboxylate
• 化学式: C₁₂H₁₅NO₂S
• 分子量: 237.323
• InChiKey: JDQCUPXTJONOEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenylthiazolidine-4-carboxylic acid ethyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 3-acetylamino-3-ethoxycarbonyldihydrothieno[2,3-g]quinolin-4,9-dione
  参考文献：
  名称：

  Reaction between quinone and thiazolidine. A study on the formation mechanism of new antiproliferative quinolindiones

  摘要：

  Reaction between quinolinquinone and thiazolidine in basic medium was investigated. 2-Arylthiazolidine-4-carboxylic acid ethyl esters undergo two different cleavages in basic medium, yielding the 1-aryl-2-azadiene and a thiolic species. In the presence of quinolinquinone, the isomeric 1-aryl-3-ethoxycarbonyl-pyridoisoquinolin-5,10-diones and 3-amino-3-ethoxycarbonyl-dihydrothienoquinolin-4,9-diones are formed by a hetero-Diels-Alder reaction and 1,4-Michael addition reaction, respectively. A mechanism for the formation of the reaction products is presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.098
• 作为产物：
  描述：

  L-半胱氨酸乙酯盐酸盐 、 苯甲醛 在 叔丁基过氧化氢 、 碘 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以99%的产率得到2-phenylthiazolidine-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  I 2 / TBHP介导的串联环化和氧化反应：容易获得2-取代的噻唑和苯并噻唑

  摘要：

  利用容易获得的半胱氨酸酯和2-氨基苯硫醇作为N和S源，已经完成了2-取代的噻唑和苯并噻唑的有效合成。反应在I 2 / TBHP系统下进行，涉及一锅串联串联和氧化过程。这种无过渡金属的方案适用于多种醛类，这为快速访问含噻唑的分子提供了另一种方法。

  DOI：

  10.1039/c8ob02826e

文献信息

• Antitumor Agents. 3. Design, Synthesis, and Biological Evaluation of New Pyridoisoquinolindione and Dihydrothienoquinolindione Derivatives with Potent Cytotoxic Activity
  作者：Adele Bolognese、Gaetano Correale、Michele Manfra、Antonio Lavecchia、Orazio Mazzoni、Ettore Novellino、Paolo La Colla、Giuseppina Sanna、Roberta Loddo

  DOI：10.1021/jm030918b

  日期：2004.2.1

  1-aryl-3-ethoxycarbonyl-pyrido[2,3-g]isoquinolin-5,10-diones (PIQDs, 1-7), were designed on the basis of a molecular model obtained by aligning the common quinolinquinone substructure of 5H-pyrido[3,2-a]phenoxazin-5-one (PPH) and some known anticancer agents. A Diels-Alder reaction between quinolin-5,8-dione (QD) and a 2-azadiene, formed by demolition of 2-aryl-1,3-thiazolidine ethyl esters (T compounds)

  根据通过比对共同点而获得的分子模型，设计了新的抗增殖化合物，即1-芳基-3-乙氧基羰基-吡啶并[2,3-g]异喹啉-5,10-二酮（PIQD，1-7）。 5H-吡啶并[3,2-a]苯恶嗪-5-one（PPH）的喹啉醌亚结构和一些已知的抗癌药。喹啉5,8-二酮（QD）与2-氮杂二烯之间的Diels-Alder反应是由2-芳基-1,3-噻唑烷乙酯（T化合物）分解形成的，用于制备1-7和异构体1-芳基-3-乙氧基羰基吡啶并[3，2-g]异喹啉-5，10-二酮（8-14）。其他两种化合物，3-氨基-3-乙氧基羰基二氢噻吩并[2,3-g]喹啉-4,9-二酮（15）和3-氨基-3-乙氧基羰基二氢噻吩并[3,2-g]喹啉-4.9 -二酮（16），是由QD的1，4迈克尔反应与通过打开T化合物形成的硫醇盐类反应而产生的，从反应混合物中回收。评估了1-16的抗增殖活性，针对代表性的人类液体和固体肿瘤细胞系。这些化合物的IC（50）的中值范围为2
• Phosphonoalkanoylamino acids
  申请人：ANALYTICAL RESEARCH PHARMACEUTICALS PTY. LTD.

  公开号：EP0091525A2

  公开（公告）日：1983-10-19

  Certain new phosphonoalkanoylamino acids of the formula (I) herein and their pharmaceutically acceptable salts exhibit improved antihypertensive properties and are particularly useful for the reduction of angiotensin related hypertension.

  某些新的式（I）膦酰基丙酰亚胺酸及其药学上可接受的盐类具有更好的降压特性，尤其适用于降低与血管紧张素相关的高血压。
• Antitumor Agents 6. Synthesis, Structure−Activity Relationships, and Biological Evaluation of Spiro[imidazolidine-4,3′-thieno[2,3-<i>g</i>]quinoline]-tetraones and Spiro[thieno[2,3-<i>g</i>]quinoline-3,5′-[1,2,4]triazinane]-tetraones with Potent Antiproliferative Activity
  作者：Adele Bolognese、Gaetano Correale、Michele Manfra、Anna Esposito、Ettore Novellino、Antonio Lavecchia

  DOI：10.1021/jm8007689

  日期：2008.12.25

  Two series of quinolinquinone derivatives, 2'H-spiro[imidazolidine-4,3'-thieno[2,3-g]quinoline]-2,4',5,9'-tetraones (2a-n) and 2H-spiro[thieno[2,3-g]quinoline-3.5'-[1,2,4]triazinane]-3',4,6',9-tetraones (3a-e), were designed and synthesized using the previously described ethyl 3-amino-4,9-dioxo-2,3,4,9-tetrahydrothieno[2,3-g]quinoline-3-carboxylate (1) as a starting material. All compounds were evaluated for their anti proliferative activity against a panel of representative liquid and solid human tumor cell lines and exhibit IC(50) values in the micromolar/submicromolar range. Series 2 displayed higher cytotoxicity than did series 3. The nature of the substituents on both imidazoline and triazinane N1 nitrogen markedly affected the activity profile of these series. Spectrophotometric and fluorescence measurements as well as Unwinding assays performed on the most cytotoxic compounds, 2c, 2g, and 2k, showed that they are nonintercalative DNA agents and inhibit the catalytic activity of Topo II in a concentration-dependent mode. 2g was the most active Topo II inhibitor with activity levels comparable to those of VP-16.
• BADR, MAHMOUD, ZARIF, AMIN;ALY, MORSY, MOHAMED;FAHMY, ATIAT, MOHAMED.;MAN+, BULL. CHEM. SOC. JAP., 1981, 54, N 6, 1844-1847
  作者：BADR, MAHMOUD, ZARIF, AMIN、ALY, MORSY, MOHAMED、FAHMY, ATIAT, MOHAMED.、MAN+

  DOI：——

  日期：——
• I₂/TBHP-Mediated tandem cyclization and oxidation reaction: Facile access to 2-substituted thiazoles and benzothiazoles
  作者：Li Liu、Chen Tan、Rong Fan、Zihan Wang、Hongguang Du、Kun Xu、Jiajing Tan

  DOI：10.1039/c8ob02826e

  日期：——

  readily available cysteine esters and 2-aminobenzenethiols as N and S sources. The reaction proceeds under an I2/TBHP system and involves a one-pot tandem cyclization and oxidation sequence. A diverse range of aldehydes is amenable for this transition-metal-free protocol, which provides an alternative method to rapidly access thiazole-containing molecules.

  利用容易获得的半胱氨酸酯和2-氨基苯硫醇作为N和S源，已经完成了2-取代的噻唑和苯并噻唑的有效合成。反应在I 2 / TBHP系统下进行，涉及一锅串联串联和氧化过程。这种无过渡金属的方案适用于多种醛类，这为快速访问含噻唑的分子提供了另一种方法。