1-苄基-3-甲基-2-硫代脲 | 2740-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苄基-3-甲基-2-硫代脲
• 英文名称: 1-methyl-3-benzyl thiourea
• 英文别名: 1-benzyl-3-methylthiourea；N-benzyl-N'-methylthiourea；N-Methyl-N'-benzyl-thioharnstoff；1-Benzyl-3-methyl-2-thiourea
• CAS: 2740-94-5
• 化学式: C₉H₁₂N₂S
• mdl: MFCD00004924
• 分子量: 180.274
• InChiKey: GDUBTTXVKWIAKV-UHFFFAOYSA-N

物化性质

• 熔点：
  74 °C
• 沸点：
  281.7±33.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 危险品运输编号：
  UN3335
• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  1-苄基-3-甲基-2-硫代脲 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 5-bromoethyl-3-benzyl-2-methyliminothiazolidin-4-one
  参考文献：
  名称：

  Use of OB-104 to treat ocular inflammation

  摘要：

  一种用于治疗和预防眼部炎症的新化合物被披露。该化合物OB-104在炎症的早期和晚期均有效。

  公开号：

  US05198454A1
• 作为产物：
  描述：

  N,N'-dimethylthioperoxydicarbamic acid 、 苄胺 以 乙醇 为溶剂， 生成 1-苄基-3-甲基-2-硫代脲
  参考文献：
  名称：

  Nair,G.V., Journal of the Indian Chemical Society, 1965, vol. 42, p. 359 - 366

  摘要：

  DOI：

文献信息

• New Benzimidazole-Derived Isothioureas as Potential Antileukemic Agents - Studies <i>In Vitro</i>
  作者：Miroslawa Koronkiewicz、Anna Romiszewska、Zdzislaw Chilmonczyk、Zygmunt Kazimierczuk

  DOI：10.2174/1573406410666141203124329

  日期：2015.4.29

  Isothioureas are a class of amphiphilic compounds carrying a highly basic isothiourea group of pKa ranging between 10 and 11. Hence, they exist in protonated (cation) form at physiological pH, a characteristic is of key importance for their pharmacological activity. Recently, we have found that a number of S-pentabromobenzylisothiourea derivatives show substantial cytotoxicity toward a variety of human glioblastoma, leukemia, and adenocarcinoma cell lines. Whereas there is a growing body of data on aliphatic and alkylaromatic isothioureas, little attention was given to this day to heterocyclic isotiourea derivatives. Here we report on the synthesis and pharmacological in vitro properties of 10 novel S-(benzimidazol-2-ylmethyl)- and S-(5,6-dichlorobenzimidazol-2-ylmethyl)isothiourea derivatives. The compounds were obtained by the condensation of the respective 2-chloromethyl benzimidazoles with various substituted N(N’)-thioureas. Besides the essential physicochemical characteristics (H-NMR, UV, elemental analysis) of the new compounds, their log P values, which are of key importance for in vivo drug distribution and interactions, were determined. Pharmacological (anticancer) activity of the compounds was evaluated based on their ability to induce apoptosis in exponentially growing cultures of the human acute myelogenous leukemia cell line KG-1; the apoptosis was assessed with a variety of flow cytometric methods. Of the novel compounds tested, the most potent apoptosis inducer in KG-1 cells was N-methyl-S- (5,6-dichloro-1H-benzimidazol-2-ylmethyl)isothiouronium chloride (ClBMMe).

  异硫脲是一种两亲性化合物的类别，携带一个高碱性的异硫脲基团，其pKa值在10到11之间。因此，它们在生理pH下以质子化（阳离子）形式存在，这一特性对它们的药理活性至关重要。最近，我们发现一些S-五溴苄基异硫脲衍生物对多种人类胶质母细胞瘤、白血病和腺癌细胞系显示出显著的细胞毒性。尽管有关脂肪族和烷基芳香族异硫脲的数据越来越多，但至今对杂环异硫脲衍生物的关注较少。在这里，我们报道了10种新型S-(苯并咪唑-2-甲基)和S-(5,6-二氯苯并咪唑-2-甲基)异硫脲衍生物的合成及其体外药理学特性。这些化合物是通过相应的2-氯甲基苯并咪唑与各种取代的N(N’)-硫脲的缩合反应获得的。除了新化合物的重要物理化学特性（H-NMR、UV、元素分析）外，还测定了它们的关键性质——log P值，这对药物在体内的分布和相互作用至关重要。通过评估这些化合物在指数增长的KG-1人类急性髓系白血病细胞系中诱导凋亡的能力来评估其药理（抗癌）活性；凋亡是通过多种流式细胞术方法评估的。在测试的新化合物中，N-甲基-S-(5,6-二氯-1H-苯并咪唑-2-甲基)异硫脲氯化物（ClBMMe）在KG-1细胞中是最有效的凋亡诱导剂。
• Tetrahydro-1,3,5-thiadiazin-4-one derivative
  申请人：Nihon Nohyaku Co., Ltd.

  公开号：US04159328A1

  公开（公告）日：1979-06-26

  A tetrahydro-1,3,5-thiadiazin-4-one represented by the general formula, ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, represent each an alkyl group, allyl group, cycloalkyl group, alkoxyalkyl group, benzyl group, phenyl group or substituted phenyl group having as substituents alkyl groups, nitro group, halogen atoms, alkoxy groups, or trifluoromethyl group and R.sup.2 and R.sup.3 may also represent hydrogen atoms, is a new compound and useful for controlling insects and mites.

  由通用公式表示的1,3,5-噻二嗪-4-酮，其中R1、R2和R3相同或不同，每个代表一个烷基、烯丙基、环烷基、烷氧基烷基、苄基、苯基或取代的苯基，取代基可以是烷基、硝基、卤素原子、烷氧基或三氟甲基，R2和R3还可以代表氢原子，这是一个新化合物，用于控制昆虫和螨虫。
• Thiazolidine derivatives
  申请人：Hoechst Aktiengesellschaft

  公开号：US04061761A1

  公开（公告）日：1977-12-06

  The invention relates to thiazolidine derivatives having in 4-position a hydroxy group and a 3'-sulphamyl-phenyl substituent, in 2-position an imino group and in 1-position an aliphatic or cycloaliphatic substituent. Said thiazolidines have diuretic activity. The invention also relates to a process for the manufacture of said compounds.

  本发明涉及在4位具有羟基和3'-磺酰氨基-苯基取代基，在2位具有亚氨基，在1位具有脂肪族或环脂肪族取代基的噻唑烷衍生物。所述噻唑烷具有利尿活性。本发明还涉及制造所述化合物的方法。
• Catalytic Asymmetric Synthesis of Quaternary Barbituric Acids
  作者：Sandra del Pozo、Silvia Vera、Mikel Oiarbide、Claudio Palomo

  DOI：10.1021/jacs.7b09124

  日期：2017.11.1

  The catalytic asymmetric α-functionalization of prochiral barbituric acids, a subtype of pseudosymmetric 1,3-diamides, to yield the corresponding 5,5-disubstituted (quaternary) derivatives remains essentially unsolved. In this study 2-alkylthio-4,6-dioxopirimidines are designed as key 1,3-diamide surrogates that perform exceedingly in amine-squaramide catalyzed C-C bond forming reactions with vinyl

  前手性巴比妥酸（假对称 1,3-二酰胺的一种亚型）的催化不对称 α-官能化产生相应的 5,5-二取代（季）衍生物基本上仍未解决。在这项研究中，2-烷硫基-4,6-二氧嘧啶被设计为关键的 1,3-二酰胺替代物，在胺-方酸酰胺催化的 CC 键形成反应中表现出色，乙烯基酮或 Morita-Baylis-Hillmann 型烯丙基溴作为亲电子试剂。加合物的温和酸水解以前所未有的对映选择性提供具有环内季碳的巴比妥酸衍生物，为生物学评估提供有价值的材料。
• N-methylthioureas as new agonists of retinoic acid receptor-related orphan receptor
  作者：Yohan Park、Suckchang Hong、Myungmo Lee、Hyojun Jung、Won-Jea Cho、Eun-Jin Kim、Ho-Young Son、Mi-Ock Lee、Hyeung-geun Park

  DOI：10.1007/s12272-012-0809-0

  日期：2012.8

  Thirty two thiourea derivatives were prepared and their agonistic activities on the retinoic acid receptor-related orphan receptor α (RORα) were evaluated. The replacement of the 3-allyl-2-imino-thiazolidin-4-one moiety of the lead compound CGP52608 (1) with various functional group substituted aromatic rings, improved the agonistic activity of RORα. Among the prepared derivatives, 1-methyl-3-(4-phenoxy-benzyl)-thiourea (32) showed 2.6-fold higher agonistic activity than CGP52608 in the RORα-activation assay.

  制备了三十二种硫脲衍生物，并评估了它们对视黄酸受体相关孤儿受体α（RORα）的激动活性。将先导化合物CGP52608（1）的3-烯丙基-2-亚氨基-噻唑烷-4-酮部分替换为各种官能团取代的芳香环，从而提高了RORα的激动活性。在制备的衍生物中，1-甲基-3-（4-苯氧基-苄基）-硫脲（32）在RORα激活试验中显示出比CGP52608高2.6倍的激动活性。

表征谱图