methyl (3R)-5-methyl-3-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]thiazole-7-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl (3R)-5-methyl-3-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]thiazole-7-carboxylate
• 英文别名: methyl (3R)-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylate；methyl (3R)-5-methyl-3-phenyl-1,3-dihydropyrrolo[1,2-c][1,3]thiazole-7-carboxylate
• 化学式: C₁₅H₁₅NO₂S
• 分子量: 273.356
• InChiKey: APPWRWBTISUVQR-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  R-2-苯基-噻唑烷-4-羧酸 、 乙酸酐 、 丙炔酸甲酯 反应 4.0h， 以55%的产率得到methyl (3R)-5-methyl-3-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]thiazole-7-carboxylate
  参考文献：
  名称：

  5H，7H-噻唑并[3,4- c ]恶唑-4-鎓-1-油酸酯的分子间偶极环加成反应

  摘要：

  （5R）-3-甲基-5-苯基5H，7H -噻唑并[3,4- Ç的范围dipolarophiles的存在下生成的]恶唑-4-鎓-1-酚盐。导致手性的合成这个介离子物种的分子间的1,3-偶极环加成1H -吡咯并[1,2- c ^ ]噻唑衍生物7A，7B，8，14，18，19和20。在与甲基和乙基乙烯基酮的反应中，还获得了螺化合物9和15。化合物15的结构 通过X射线晶体学测定。

  DOI：

  10.1016/s0040-4020(00)00243-x

文献信息

• Chiral 6-hydroxymethyl-1H,3H-pyrrolo[1,2-c]thiazoles: Novel antitumor DNA monoalkylating agents
  作者：Maria I.L. Soares、Ana Filipa Brito、Mafalda Laranjo、Ana Margarida Abrantes、M. Filomena Botelho、José A. Paixão、Ana Matos Beja、Manuela Ramos Silva、Teresa M.V.D. Pinho e Melo

  DOI：10.1016/j.ejmech.2010.07.029

  日期：2010.10

  New chiral 1H,3H-pyrrolo[1,2-c]thiazoles were synthesized and screened for their in vitro activity as anti-cancer agents in three human tumor cell lines, colorectal adenocarcinoma, melanoma and breast adenocarcinoma. (R)-6-Hydroxymethyl-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazole and the corresponding benzylcarbamate showed selectivity for breast cancer cell lines with IC(50) values of 24 mu M and 2.2 mu M, respectively. The latter also showed significant activity against colorectal adenocarcinoma cancer cell lines (IC(50) = 8.7 mu M) In contrast, the 7-hydroxymethyl-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c] thiazole gave moderate anti-cancer activity. The performance against breast cancer cell lines (IC(50) = 10 mu M) of a potential bisalkylating agent, a (3R)-6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c] thiazole, wasn't significantly different from the one observed for the monoalkylating derivatives indicating that the main mechanism of action may in fact be the monoalkylation process. (C) 2010 Elsevier Masson SAS. All rights reserved
• Intermolecular Dipolar Cycloaddition Reactions of 5H,7H-Thiazolo[3,4-c]oxazol-4-ium-1-olates
  作者：Teresa M.V.D. Pinho e Melo、Maria I.L. Soares、Dália M. Barbosa、António M.d'A. Rocha Gonsalves、Ana Matos Beja、José A. Paixão、Manuela Ramos Silva、Luiz Alte da Veiga

  DOI：10.1016/s0040-4020(00)00243-x

  日期：2000.5

  (5R)-3-Methyl-5-phenyl-5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olate was generated in the presence of a range of dipolarophiles. The intermolecular 1,3-dipolar cycloaddition of this mesoionic species led to the synthesis of chiral 1H-pyrrolo[1,2-c]thiazole derivatives 7a, 7b, 8, 14, 18,19 and 20. In the reaction with methyl and ethyl vinyl ketone, spiro compounds 9 and 15 were also obtained. The structure

  （5R）-3-甲基-5-苯基5H，7H -噻唑并[3,4- Ç的范围dipolarophiles的存在下生成的]恶唑-4-鎓-1-酚盐。导致手性的合成这个介离子物种的分子间的1,3-偶极环加成1H -吡咯并[1,2- c ^ ]噻唑衍生物7A，7B，8，14，18，19和20。在与甲基和乙基乙烯基酮的反应中，还获得了螺化合物9和15。化合物15的结构 通过X射线晶体学测定。