1-(methoxymethyl)-2-(phenylthio)-1H-imidazole | 67319-05-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(methoxymethyl)-2-(phenylthio)-1H-imidazole
• 英文别名: 1-(methoxymethyl)-2-(phenylthio)imidazole；1-methoxymethyl-2-phenylthioimidazole；1-methoxymethyl-2-phenylsulfanyl-1H-imidazole；1-methoxymethyl-2phenylthioimidazole；N-Methoxymethyl-2-phenylmercaptoimidazol；1-(methoxymethyl)-2-phenylsulfanylimidazole
• CAS: 67319-05-5
• 化学式: C₁₁H₁₂N₂OS
• 分子量: 220.295
• InChiKey: GBNYQUIYMCRWFY-UHFFFAOYSA-N

物化性质

• 沸点：
  372.8±44.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(methoxymethyl)-2-(phenylthio)-1H-imidazole 在 aluminium amalgam 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 42.5h， 生成 4-diphenylhydroxymethyl-1-methoxymethyl-imidazole
  参考文献：
  名称：

  Synthesis and structure-activity of 4(5)-(2,2-diphenylethyl)imidazoles as new α2-adrenoreceptor antagonists

  摘要：

  DOI：

  10.1016/0223-5234(90)90180-b
• 作为产物：
  描述：

  1-(甲氧基甲基)-1H-咪唑 、 二苯二硫醚 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以62%的产率得到1-(methoxymethyl)-2-(phenylthio)-1H-imidazole
  参考文献：
  名称：

  Dragmacidin D的合成研究：三个片段的合成和组装迈向高级中间体

  摘要：

  我们在此报告了合成具有生物活性的海洋天然产物 Dragmacidin D 的关键高级中间体的方法。通过采用三个片段（5、7 和 8）的模块化合成策略，高级中间体 3 已在 2.5 中成功合成从硝基甲苯 20 开始，经过 15 个步骤的 % 产率。该合成还涉及顺序交叉偶联反应，即 Sonogashira 和 Suzuki-Miyaura 反应，因此可以有效地合成各种类似物，这将允许研究药物的构效关系D.

  DOI：

  10.1002/ejoc.201100242

文献信息

• Synthetic studies on dragmacidin D: synthesis of the left-hand fragment
  作者：Minoru Ikoma、Masato Oikawa、Makoto Sasaki

  DOI：10.1016/j.tetlet.2008.10.020

  日期：2008.12

  We report a synthesis of a left-hand fragment of bis(indole)-class marine alkaloid, dragmacidin D. The synthesis features Suzuki–Miyaura reaction for the coupling of imidazolyl boronic acid and (4-indolyl)vinyl bromide.

  我们报告了双（吲哚）类海洋生物碱，德拉莫达丁D的左手片段的合成。该合成具有Suzuki-Miyaura反应，用于咪唑基硼酸和（4-吲哚基）乙烯基溴的偶联。
• Extending Pummerer Reaction Chemistry: Studies in the Palau’amine Synthesis Area
  作者：Ken S. Feldman、Ahmed Yimam Nuriye、Jianfeng Li

  DOI：10.1021/jo200740b

  日期：2011.6.17

  Exploratory oxidative cyclization studies on cyclopentanelated and cyclohexenelated oroidin derivatives utilized Pummerer chemistry to generate pentacyclic structures related to the palau’amine family of sponge metabolites. Stereochemical issues were paramount, and appropriate choice of annelated ring size led to formation of the pentacyclic framework with complete diastereoselectivity for all of the

  对环戊烷化和环己烯醇吗啡衍生物的探索性氧化环化研究利用Pummerer化学方法生成了与海绵代谢产物的帕劳胺家族有关的五环结构。立体化学问题是最重要的，和稠合环大小的适当选择导致形成与所有核心债券的完整非对映选择性五环框架。
• Synthesis of a regio-isomer of kealiiquinone, a marine benzimidazole alkaloid
  作者：Seikou Nakamura、Naoki Tsuno、Masayuki Yamashita、Ikuo Kawasaki、Shunsaku Ohta、Yoshitaka Ohishi

  DOI：10.1039/b007560o

  日期：——

  Treatment of 1,3-dialkyl-2-(phenylthio)benzimidazolium salts 3 and 1,3-dialkyl-2-phenylthio-1H-imidazolium salts 7 with aq. K2CO3 gives 1,3-dialkyl-1,3-dihydrobenzimidazol-2-ones 4 and 1,3-dialkyl-1,3-dihydroimidazol-2-ones 8, respectively, in 22–94% yield. A regio-isomer 17 of kealiiquinone, a marine benzimidazole alkaloid, where the 4-methoxyphenyl group at the 4-position migrates to the 9-position, is synthesized by application of the reaction. Cytotoxity of 17 and kealiiquinone against 39 human cancer cells is evaluated. They have weak activity but a unique mechanism of action.

  用碱性 K2CO3 处理 1,3-二烷基-2-(苯硫基)苯并咪唑鎓盐 3 和 1,3-二烷基-2-苯硫基-1H-咪唑鎓盐 7，可分别得到 1,3-二烷基-1,3-二氢苯并咪唑-2-酮 4 和 1,3-二烷基-1,3-二氢咪唑-2-酮 8，收率为 22-94%。应用该反应还合成了海洋苯并咪唑生物碱 kealiiquinone 的一个regio-异构体 17，其中 4 位上的 4-甲氧基苯基迁移到了 9 位。评估了 17 和 kealiiquinone 对 39 种人类癌细胞的细胞毒性。它们的活性较弱，但作用机制独特。
• Granulatimide compounds and uses thereof
  申请人：The University of British Columbia

  公开号：US06291447B1

  公开（公告）日：2001-09-18

  Novel granulatimide compounds and pharmaceutical formulations thereof are provided. Compounds of this invention have the general formula: wherein are independently R or Z as defined below, or in combination F and F′ is Ar1 as defined below; Ar1 is a monocyclic, bicyclic or tricyclic, fully or partially aromatic system containing five or six membered carbocyclic or, oxygen, nitrogen or sulphur containing heterocyclic rings, optionally substituted with R or Z; W is selected from the group consisting of formula (i); (ii) or (iii), wherein the structures are as follows:

  本发明提供了新型的颗粒状酰胺化合物及其制药组合物。该发明的化合物具有以下通式：其中R或Z独立地定义如下，或者F和F'的组合是以下定义的Ar1；Ar1是一个含有五个或六个成员的碳环或含氧、氮或硫杂环的单环、双环或三环、完全或部分芳香性系统，可选地取代R或Z；W从以下公式（i）、（ii）或（iii）的群组中选取，结构如下：
• Granulatimide and Isogranulatimide, Aromatic Alkaloids with G2 Checkpoint Inhibition Activity Isolated from the Brazilian Ascidian <i>Didemnum </i><i>granulatum</i>:  Structure Elucidation and Synthesis
  作者：Roberto G. S. Berlinck、Robert Britton、Edward Piers、Lynette Lim、Michel Roberge、Rosana Moreira da Rocha、Raymond J. Andersen

  DOI：10.1021/jo981607p

  日期：1998.12.1

  Crude methanol ex-tracts of the ascidian Didemum granulatum collected in Brazil showed activity in a new screen for G2 cell cycle checkpoint inhibitors. Bioassay-guided fractionation of the extract yielded the known alkaloids didemnimides A (1) and D (2), the new alkaloid didemnimide E (3), and a new G2 checkpoint inhibitor. Two candidate structures for the inhibitor, named granulatimide (4) and isogranulatimide (5), have been prepared via a short and efficient biomimetic synthesis involving the photolysis of didemnimide A (1). The synthesis revealed that the correct structure for the naturally occurring G2 checkpoint inhibitor is isogranulatimide (5). Granulatimide (4), the other candidate structure, was also found to be a G2 checkpoint inhibitor, and it was subsequently detected in chromatographic fractions associated with purification of D. granulatum alkaloids. Granulatimide (4) and isogranulatimide (5) represent the first examples of a new class of G2 specific cell cycle checkpoint inhibitors and the first ones identified through a rational screening program.