dimethyl 2-(methylthio)-1-phenylimidazole-4,5-dicarboxylate | 117120-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dimethyl 2-(methylthio)-1-phenylimidazole-4,5-dicarboxylate
• 英文别名: dimethyl 2-(methylthio)-1-phenyl-4,5-imidazoledicarboxylate；dimethyl 2-methylsulfanyl-1-phenylimidazole-4,5-dicarboxylate
• CAS: 117120-96-4
• 化学式: C₁₄H₁₄N₂O₄S
• 分子量: 306.342
• InChiKey: NIESYWLUXQWEGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  95.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(methylthio)-1-phenylimidazole-4,5-dicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以81%的产率得到1-phenyl-2-(methylthio)-4,5-bis (hydroxymethyl)imidazole
  参考文献：
  名称：

  Design, synthesis, antineoplastic activity, and chemical properties of bis(carbamate) derivatives of 4,5-bis(hydroxymethyl)imidazole

  摘要：

  A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia. Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds. However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active. The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia. The solution stability, water solubility, pKa, and log P of carmethizole are also reported.

  DOI：

  10.1021/jm00121a023
• 作为产物：
  描述：

  dimethyl 3-phenyl-2-sulfanylidene-1H-imidazole-4,5-dicarboxylate 、 碘甲烷 以80%的产率得到
  参考文献：
  名称：

  ANDERSON, W. K.;BHATTACHARJEE, D.;HOUSTON, D. M., J. MED. CHEM., 32,(1989) N, C. 119-127

  摘要：

  DOI：

文献信息

• Bis(acyloxmethyl)imidazole compounds
  申请人：The Research Foundation of State University of New York

  公开号：US05329012A1

  公开（公告）日：1994-07-12

  This invention relates to new bis(acyloxymethyl)imidazole derivatives; to compositions comprising these derivatives; and to processes for their utility as fungicides, bactericides and as inhibitors of the growth of cancer, particularly solid tumor cancer, in warm blooded animals of the formula: ##STR1## wherein M is ##STR2## or R; each R, R' and R" are independently selected from hydrogen and Z substituted or unsubstituted alkyl, cycloalkyl, cycloalkenyl, alkenyl, aryl, and heterocyclic ring wherein said ring comprises at least one of oxygen, nitrogen, sulfur or silicon; provided that ##STR3## may form a Z substituted or unsubstituted heterocyclic, and R' and R" attached to the imidazole ring, may form a Z substituted or unsubstituted heterocyclic ring; X is selected from at least one of oxygen, sulfur, nitrogen and alkyl; provided further that silicon is not directly attached to oxygen, sulfur or nitrogen and R' is not hydrogen when X is oxygen or sulfur; and Z is selected from halogen, nitro, nitrile, alkyl, haloalkyl, alkenyl, carboxylic acid, carboxylic acid ester, carboxylic acid amide, ether, thioether, hydroxyl, acylated hydroxyl, sulfonylamide, sulfonylurea, sulfoxide, sulfone, substituted and unsubstituted amine or mixtures thereof.

  本发明涉及新的双(酰氧甲基)咪唑衍生物；包括这些衍生物的组合物；以及将它们作为杀真菌剂、杀菌剂和抑制癌症生长的过程，特别是在温血动物中用于固体肿瘤癌症的过程，其化学式为：##STR1## 其中M是##STR2##或R；每个R、R'和R"独立地选择氢和Z取代或未取代的烷基、环烷基、环烯基、烯基、芳基和杂环环，其中所述环至少包括氧、氮、硫或硅中的一种；但##STR3##可以形成取代或未取代的杂环，而附在咪唑环上的R'和R"可以形成取代或未取代的杂环环；X选择至少由氧、硫、氮和烷基中的一种；进一步提供的是，硅没有直接连接到氧、硫或氮，当X是氧或硫时，R'不是氢；Z选择卤素、硝基、腈、烷基、卤代烷基、烯基、羧酸、羧酸酯、羧酸酰胺、醚、硫醚、羟基、酰化羟基、磺酰胺、磺酰脲、亚砜、砜、取代和未取代胺或其混合物。
• ANDERSON, W. K.;BHATTACHARJEE, D.;HOUSTON, D. M., J. MED. CHEM., 32,(1989) N, C. 119-127
  作者：ANDERSON, W. K.、BHATTACHARJEE, D.、HOUSTON, D. M.

  DOI：——

  日期：——
• Bis (acyloxymethyl) imidazole Derivative
  申请人：THE RESEARCH FOUNDATION OF STATE UNIVERSITY OF NEW YORK

  公开号：EP0313724B1

  公开（公告）日：1995-08-09
• US5329012A
  申请人：——

  公开号：US5329012A

  公开（公告）日：1994-07-12
• Design, synthesis, antineoplastic activity, and chemical properties of bis(carbamate) derivatives of 4,5-bis(hydroxymethyl)imidazole
  作者：Wayne K. Anderson、Debkumar Bhattacharjee、D. Michael Houston

  DOI：10.1021/jm00121a023

  日期：1989.1

  A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia. Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds. However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active. The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia. The solution stability, water solubility, pKa, and log P of carmethizole are also reported.