diethyl 2-mercapto-1-phenylimidazole-4,5-dicarboxylate | 117121-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: diethyl 2-mercapto-1-phenylimidazole-4,5-dicarboxylate
• 英文别名: 1-phenyl-2-thioxo-2,3-dihydro-1H-imidazole-4,5-dicarboxylic acid diethyl ester；1-Phenyl-2-thioxo-2,3-dihydro-1H-imidazol-4,5-dicarbonsaeure-diaethylester；Diethyl 2-mercapto-1-phenyl-4,5-imidazoledicarboxylate；diethyl 3-phenyl-2-sulfanylidene-1H-imidazole-4,5-dicarboxylate
• CAS: 117121-07-0
• 化学式: C₁₅H₁₆N₂O₄S
• 分子量: 320.369
• InChiKey: PJLJARJJENHAGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-mercapto-1-phenylimidazole-4,5-dicarboxylate 在 lithium aluminium tetrahydride 、 sodium methylate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 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：

  N-phenyl-N-formylglycine ethyl ester 、 草酸二乙酯 在 盐酸 、 potassium thioacyanate 、 sodium 作用下， 生成 diethyl 2-mercapto-1-phenylimidazole-4,5-dicarboxylate
  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

文献信息

• First catalytic hetero-Diels–Alder reaction of imidazole-2-thiones and in silico biological evaluation of the cycloadducts
  作者：Nikolaos Eleftheriadis、Evanthia Samatidou、Constantinos G. Neochoritis

  DOI：10.1016/j.tet.2016.02.034

  日期：2016.4

  reactions of suitably substituted imidazole-2-thiones with dienes were studied. It was found that the electron density of the imidazole core influenced the reaction, since electron withdrawing groups led to the novel spiro-derivatives 2 whereas electron donating groups gave rise to the sulfur substituted imidazole derivatives 6. The reaction conditions were optimized and full assignment of all 1H and 13C

  研究了路易斯酸催化适当取代的咪唑-2-硫酮与二烯的狄尔斯-阿尔德反应。发现咪唑核心的电子密度影响了反应，因为吸电子基团导致了新型螺衍生物2，而供电子基团产生了硫取代的咪唑衍生物6。优化了反应条件，并明确实现了所有1 H和13 C NMR化学位移的完全分配。在计算机上通过三种不同蛋白质的分子建模对环加合物进行了计算机评估，并计算了ADME-Tox特性。
• 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。
• Bis (acyloxymethyl) imidazole Derivative
  申请人：THE RESEARCH FOUNDATION OF STATE UNIVERSITY OF NEW YORK

  公开号：EP0313724A2

  公开（公告）日：1989-05-03

  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: wherein M is N < or R: each R, R', and R" are independently selected from hydrogen and Z substituted or unsubstituted alkyl, cycloalkyl, cycloalkenyi, alkenyl, aryl, and heterocyclic ring wherein said ring comprises at least one of oxygen, nitrogen, sulfur or silicon; provided that N < 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(酰氧基甲基)咪唑衍生物；涉及包含这些衍生物的组合物；涉及它们作为杀真菌剂、杀细菌剂和作为癌症（尤其是实体瘤癌症）生长抑制剂在温血动物中的应用过程，其式如下： 其中 M 是 N < 或 R：每个 R、R'和 R "独立地选自氢和 Z 取代或未取代的烷基、环烷基、环烯基、烯基、芳基和杂环，其中所述环包括氧、氮、硫或硅中的至少一种；条件是 N < 可形成 Z 取代或未取代的杂环，而连接到咪唑环上的 R 和 R 可形成 Z 取代或未取代的杂环；X 选自氧、硫、氮和烷基中的至少一种；条件是硅不直接与氧、硫或氮相连，且当 X 为氧或硫时，R'不是氢；Z 选自卤素、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、磺酰酰胺、磺酰脲、亚砜、砜、取代和未取代的胺或它们的混合物。
• Studies on Imidazoles. V. The S-Alkylation of 2-Mercaptoimidazoles with Esters
  作者：Reuben G. Jones

  DOI：10.1021/ja01124a510

  日期：1952.2
• 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：——