ethyl 5-(benzo[d][1,3]dioxol-5-yl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate | 327032-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: ethyl 5-(benzo[d][1,3]dioxol-5-yl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate
• 英文别名: ethyl 5-(benzo[1,3]dioxol-5-yl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate；ethyl 5-(1,3-benzodioxol-5-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate；ethyl 5-(1,3-benzodioxol-5-yl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• CAS: 327032-80-4
• 化学式: C₁₇H₁₆N₂O₅S
• 分子量: 360.39
• InChiKey: MASAWHHQNXHKRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5-(benzo[d][1,3]dioxol-5-yl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate 、 对氟苯甲醛 在 乙酸酐 、 溶剂黄146 、 zinc(II) chloride 作用下， 反应 9.0h， 以36%的产率得到diethyl 2,2'-((4-fluorophenyl)methylene)bis(5-(benzo[d][1,3]dioxol-5-yl)-3-hydroxy-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate)
  参考文献：
  名称：

  One-pot Synthesis of 1,2,3,4-Tetrahydropyrimidin-2(1H)-thione Derivatives and their Biological Activity

  摘要：

  2‐Thioxo/oxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate derivatives 2a, 2b, 2c, 2d were prepared by the reaction of ethyl acetoacetate and thiourea or urea with aldehydes using NH4Cl as a catalyst. Compounds 2a and 2c reacted with mono and bihalogenated compounds such as ethyl iodide, chloroacetonitrile, epichlorohydrin, acetyl chloride, ethyl bromoacetate, chloroacetic acid, chloroacetylchloride, and/or oxalyl chloride to afford compounds 3, 4a, 4b, 5, 6a, 6b, 7, 8, 9 and 10, respectively. Compounds 2a, 2c, and 7 were allowed to react with p‐fluorobenzaldehyde to yield the corresponding products 11a, 11b, and 12, respectively. Oxidation of 2a and 2c gave 2b, 13a, 13b, 14, 15, 16 dependent on the oxidizing agent used. Vilsmeiere‐Haack formylation of 2a and 2b with POCl3/DMF afforded 17a and 17b. Chlorination of 2b and 2d gave the chlorinated derivative 18a and 18b, which reacted with thiourea to give thioureidopyrimidine 19a and 19b. Reactions of 2a with hydrazine monohydrate, semicarbazide hydrochloride, and sodium hydroxide gave compounds 20, 21, 22, respectively. The cytotoxicity and in vitro anticancer evaluation of some prepared compounds have been assessed against two different human tumor cell lines including breast adenocarcinoma MCF‐7 and human hepatocellular carcinoma HepG2. Antimicrobial and antioxidant activities of some compounds were investigated. The newly synthesized compounds were characterized by IR, 1H‐NMR, 13C‐NMR, and mass spectral data.

  DOI：

  10.1002/jhet.2358
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 氯化铵 、 三乙胺 作用下， 以 苯 为溶剂， 反应 10.0h， 生成 ethyl 5-(benzo[d][1,3]dioxol-5-yl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  One-pot Synthesis of 1,2,3,4-Tetrahydropyrimidin-2(1H)-thione Derivatives and their Biological Activity

  摘要：

  2‐Thioxo/oxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate derivatives 2a, 2b, 2c, 2d were prepared by the reaction of ethyl acetoacetate and thiourea or urea with aldehydes using NH4Cl as a catalyst. Compounds 2a and 2c reacted with mono and bihalogenated compounds such as ethyl iodide, chloroacetonitrile, epichlorohydrin, acetyl chloride, ethyl bromoacetate, chloroacetic acid, chloroacetylchloride, and/or oxalyl chloride to afford compounds 3, 4a, 4b, 5, 6a, 6b, 7, 8, 9 and 10, respectively. Compounds 2a, 2c, and 7 were allowed to react with p‐fluorobenzaldehyde to yield the corresponding products 11a, 11b, and 12, respectively. Oxidation of 2a and 2c gave 2b, 13a, 13b, 14, 15, 16 dependent on the oxidizing agent used. Vilsmeiere‐Haack formylation of 2a and 2b with POCl3/DMF afforded 17a and 17b. Chlorination of 2b and 2d gave the chlorinated derivative 18a and 18b, which reacted with thiourea to give thioureidopyrimidine 19a and 19b. Reactions of 2a with hydrazine monohydrate, semicarbazide hydrochloride, and sodium hydroxide gave compounds 20, 21, 22, respectively. The cytotoxicity and in vitro anticancer evaluation of some prepared compounds have been assessed against two different human tumor cell lines including breast adenocarcinoma MCF‐7 and human hepatocellular carcinoma HepG2. Antimicrobial and antioxidant activities of some compounds were investigated. The newly synthesized compounds were characterized by IR, 1H‐NMR, 13C‐NMR, and mass spectral data.

  DOI：

  10.1002/jhet.2358

文献信息

• Use of derivatives of 3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine or of 3-oxo-2,3-dihydro-5H-imidazolo[3,2-a]pyrimidine for the preparation of pharmaceutical compositions intended for the treatment of cancer
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP2000140A1

  公开（公告）日：2008-12-10

  The present invention is related to the use of a compound of formula (I) for the preparation of a pharmaceutical composition intended for the treatment of cancer and in particular for the treatment of the prostate cancer, hepatocarcinomas, head and neck cancer, oesophagus cancer, thyroid gland cancer or non-hodgkinian lymphomas and some new compounds and pharmaceutical compositions containing them.

  本发明涉及使用式（I）的化合物制备用于治疗癌症的药物组合物，特别是用于治疗前列腺癌、肝癌、头颈癌、食管癌、甲状腺癌或非霍奇金淋巴瘤的药物组合物，以及一些新的化合物和含有它们的药物组合物。
• One-pot Synthesis of 1,2,3,4-Tetrahydropyrimidin-2(1<i>H</i>)-thione Derivatives and their Biological Activity
  作者：Mounir A. I. Salem、Magda I. Marzouk、Marwa S. Salem、Ghazala A. Alshibani

  DOI：10.1002/jhet.2358

  日期：2016.3

  2‐Thioxo/oxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate derivatives 2a, 2b, 2c, 2d were prepared by the reaction of ethyl acetoacetate and thiourea or urea with aldehydes using NH4Cl as a catalyst. Compounds 2a and 2c reacted with mono and bihalogenated compounds such as ethyl iodide, chloroacetonitrile, epichlorohydrin, acetyl chloride, ethyl bromoacetate, chloroacetic acid, chloroacetylchloride, and/or oxalyl chloride to afford compounds 3, 4a, 4b, 5, 6a, 6b, 7, 8, 9 and 10, respectively. Compounds 2a, 2c, and 7 were allowed to react with p‐fluorobenzaldehyde to yield the corresponding products 11a, 11b, and 12, respectively. Oxidation of 2a and 2c gave 2b, 13a, 13b, 14, 15, 16 dependent on the oxidizing agent used. Vilsmeiere‐Haack formylation of 2a and 2b with POCl3/DMF afforded 17a and 17b. Chlorination of 2b and 2d gave the chlorinated derivative 18a and 18b, which reacted with thiourea to give thioureidopyrimidine 19a and 19b. Reactions of 2a with hydrazine monohydrate, semicarbazide hydrochloride, and sodium hydroxide gave compounds 20, 21, 22, respectively. The cytotoxicity and in vitro anticancer evaluation of some prepared compounds have been assessed against two different human tumor cell lines including breast adenocarcinoma MCF‐7 and human hepatocellular carcinoma HepG2. Antimicrobial and antioxidant activities of some compounds were investigated. The newly synthesized compounds were characterized by IR, 1H‐NMR, 13C‐NMR, and mass spectral data.