methyl 1H-benzo[d]imidazole-1-carbodithioate | 1179931-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: methyl 1H-benzo[d]imidazole-1-carbodithioate
• 英文别名: Methyl benzimidazole-1-carbodithioate
• CAS: 1179931-67-9
• 化学式: C₉H₈N₂S₂
• 分子量: 208.308
• InChiKey: ARGUAEBBEMMFBN-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  363.7±25.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1H-benzo[d]imidazole-1-carbodithioate 在 Leptosphaeria maculans 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以62%的产率得到苯并咪唑
  参考文献：
  名称：

  Metabolism and Metabolites of Dithiocarbamates in the Plant Pathogenic Fungus Leptosphaeria maculans

  摘要：

  Synthetic compounds containing a dithiocarbamate group are known to have a variety of biological effects and applications including antifungal, herbicidal, and insecticidal application. Leptosphaeria maculans is a fungal pathogen of crucifers able to detoxify efficiently the only plant natural product containing a dithiocarbamate group, the phytoalexin brassinin. To evaluate the effects of dithiocarbamates on L. maculans, a number of structurally diverse S-methyl dithiocarbamates containing indolyl, biphenyl, and benzimidazolyl moieties were synthesized, and their antifungal activities and metabolism by L. maculans were investigated. All dithiocarbamates were transformed by L. maculans through hydrolysis to the corresponding amines, which were less antifungal than the parent compounds. Two dithiocarbonates were shown to be much less antifungal than the corresponding dithiocarbamates. Results of this investigation indicate that S-methyl dithiocarbamates are not useful inhibitors of L. maculans and that their rates of transformation by L. maculans did not correlate with the antifungal activity of the particular compound.

  DOI：

  10.1021/jf302038a
• 作为产物：
  描述：

  苯并咪唑 、 二硫化碳 在 potassium phosphate 作用下， 以 N,N-二甲基甲酰胺 、 N,N-dimethyl-d₆-formamide 为溶剂， 反应 0.41h， 以70%的产率得到methyl 1H-benzo[d]imidazole-1-carbodithioate
  参考文献：
  名称：

  Madhu; Tangeda, Saritha Jyostna; Qarlapati, Achaiah, Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 2, p. 173 - 176

  摘要：

  DOI：

文献信息

• Sequential Xanthalation and <i>O</i>-Trifluoromethylation of Phenols: A Procedure for the Synthesis of Aryl Trifluoromethyl Ethers
  作者：Makoto Yoritate、Allyn T. Londregan、Yajing Lian、John F. Hartwig

  DOI：10.1021/acs.joc.9b02717

  日期：2019.12.20

  known methods to synthesize aryl trifluoromethyl ethers require harsh reagents and highly controlled reaction conditions and rarely occur when heteroaromatic units are present. The two-step O-trifluoromethylation of phenols via aryl xanthates is one such method that suffers from these drawbacks. Herein, we report a method for the synthesis of aryl trifluoromethyl ethers from phenols by the facile conversion

  含有三氟甲氧基芳基的分子由于其独特的物理和电子特性而在药物，农业化学和材料科学研究中受到关注。许多已知的合成芳基三氟甲基醚的方法需要苛刻的试剂和高度受控的反应条件，并且当存在杂芳族单元时很少发生。经由芳基黄原酸酯的酚的两步O-三氟甲基化是遭受这些缺点的一种这样的方法。本文中，我们报道了一种通过用新合成的咪唑鎓甲基硫代羰基硫代硫酸盐将苯酚轻松转化为相应的芳基和杂芳基黄原酸酯并在温和的反应条件下将这些黄原酸酯转化为三氟甲基醚的方法，从苯酚合成芳基三氟甲基醚的方法。
• Azole–carbodithioate hybrids as vaginal anti-Candida contraceptive agents: Design, synthesis and docking studies
  作者：Lalit Kumar、Nand Lal、Vikash Kumar、Amit Sarswat、Santosh Jangir、Veenu Bala、Lokesh Kumar、Bhavana Kushwaha、Atindra K. Pandey、Mohammad I. Siddiqi、Praveen K. Shukla、Jagdamba P. Maikhuri、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1016/j.ejmech.2013.09.007

  日期：2013.12

  Azole and carbodithioate hybrids were synthesized as alkyl 1H-azole-1-carbodithioates (7-27) and evaluated for spermicidal/microbicidal activities against human sperm, Trichomonas vaginalis and Candida species. Seventeen compounds (7-14, 16-18 and 20-25) showed spermicidal activity at MEC 1.0% (w/v) and permanently immobilized 100% normal human spermatozoa within similar to 30 s. Seventeen compounds (7-11, 13-18 and 20-25) exhibited anti-Candida activity (IC50 1.26-47.69 mu g/mL). All compounds were devoid of bactericidal activity against four bacterial strains (50.00 mu g/mL) and antiprotozoal activity against Trichomonas vaginalis (200.00 mu g/mL). Four promising compounds (10, 17, 20 and 22) have better safety profile as compared to Nonoxyno1-9 (N-9). Docking study was done to visualize the possible interaction of designed scaffold with prospective receptor (Cyp51) of Candida albicans. (C) 2013 Elsevier Masson SAS. All rights reserved.
• WO2024091542A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Metabolism and Metabolites of Dithiocarbamates in the Plant Pathogenic Fungus Leptosphaeria maculans
  作者：M. Soledade C. Pedras、Vijay K. Sarma-Mamillapalle

  DOI：10.1021/jf302038a

  日期：2012.8.15

  Synthetic compounds containing a dithiocarbamate group are known to have a variety of biological effects and applications including antifungal, herbicidal, and insecticidal application. Leptosphaeria maculans is a fungal pathogen of crucifers able to detoxify efficiently the only plant natural product containing a dithiocarbamate group, the phytoalexin brassinin. To evaluate the effects of dithiocarbamates on L. maculans, a number of structurally diverse S-methyl dithiocarbamates containing indolyl, biphenyl, and benzimidazolyl moieties were synthesized, and their antifungal activities and metabolism by L. maculans were investigated. All dithiocarbamates were transformed by L. maculans through hydrolysis to the corresponding amines, which were less antifungal than the parent compounds. Two dithiocarbonates were shown to be much less antifungal than the corresponding dithiocarbamates. Results of this investigation indicate that S-methyl dithiocarbamates are not useful inhibitors of L. maculans and that their rates of transformation by L. maculans did not correlate with the antifungal activity of the particular compound.
• Madhu; Tangeda, Saritha Jyostna; Qarlapati, Achaiah, Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 2, p. 173 - 176
  作者：Madhu、Tangeda, Saritha Jyostna、Qarlapati, Achaiah

  DOI：——

  日期：——