2-amino-N-methylthiobenzamide | 2415-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-N-methylthiobenzamide
• 英文别名: Benzenecarbothioamide, 2-amino-N-methyl-；2-amino-N-methylbenzenecarbothioamide
• CAS: 2415-10-3
• 化学式: C₈H₁₀N₂S
• 分子量: 166.247
• InChiKey: DDBSWGLLYLTWRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-N-methylthiobenzamide 在 TEA 、 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 3.0h， 生成 2-(4-methylphenyl)-3-methylquinazoline-4-thione
  参考文献：
  名称：

  2-苯甲酰基氨基-N-甲基-硫代苯甲酰胺的环化成3-甲基-2-苯基喹唑啉-4-硫酮

  摘要：

  2-氨基的酰化ñ -甲基-硫代苯甲酰胺与取代的苯甲酰氯已被用于合成相应的2- benzoylamino- Ñ -methylthiobenzamides。随后甲醇钠催化的闭环得到相应的3-甲基-2-苯基喹唑啉-4-硫酮。这些化合物通过其1 H-和12 C-NMR光谱进行表征。在甲醇钠的甲醇溶液中，于100°C进行UV-VIS光谱分析，跟踪环化反应的动力学。

  DOI：

  10.1002/jhet.5570430521
• 作为产物：
  描述：

  2-氨基-N-甲基苯甲酰胺 在 吡啶 、 tetraphosphorus decasulfide 、 水 作用下， 生成 2-amino-N-methylthiobenzamide
  参考文献：
  名称：

  Synthesis and Pharmacological Activity of Triazole Derivatives Inhibiting Eosinophilia

  摘要：

  In order to develop novel antiasthmatic agents based on a new mechanism of action, a series of 3-substituted 5-amino-1-[(methylamino)(thiocarbonyl)]-1H-1,2,4-triazole derivatives were synthesized and evaluated in a model in which eosinophilia was induced in the ah-way through intravenous (iv) injection of Sephadex particles on days 0, 2, and 5. After screening of several hundred derivatives, we finally identified the highly potent eosinophilia inhibitor 5-amino-3-(4-chlorophenyl)-1-[(methylamino)(thiocarbonyl)]-1H-triazole (23c, GCC-AP0341), which had ID50 values of 0.3 and 0.07 mg/kg when administered orally (os) and intraperitoneally tip), respectively. This compound showed complete inhibition of the hypersensitivity induced by ascaris inhalation at an ip dose of 1 mg/kg as well as low toxicity, with an LD(50) value of > 2.0 g/kg in mice. Extensive study of its mechanism of action revealed that 23c inhibited eosinophil survival induced by interleukin-5 (IL-5), but had little or no effect on leukotriene D-4 (LTD(4)) or platelet-activating factor (PAF)-induced responses. Taken together, these results suggest 23e as a novel candidate for the treatment of chronic asthma. Further studies are now underway.

  DOI：

  10.1021/jm9507993

文献信息

• Addition reactions of heterocyclic compounds. Part 74. Products from dimethyl acetylenedicarboxylate with thiourea, thioamide, and guanidine derivatives
  作者：R. Morrin Acheson、John D. Wallis

  DOI：10.1039/p19810000415

  日期：——

  in acetonitrile gave a fused thiazolidinone derivative, but in methanol a fused thiazinone was obtained. Structures were assigned to adducts from other thioureas by comparison with the 13C n.m.r. spectra for these compounds. A method has been developed for distinguishing between the possible structural types of adducts for guanidine and amidine derivatives with DMAD using 1H and 13C n.m.r. spectroscopy

  将苯并咪唑-2-硫酮与乙炔二甲酸二甲酯（DMAD）在乙腈中混合，得到稠合的噻唑烷酮衍生物，但在甲醇中，得到了稠合的噻嗪酮。通过与这些化合物的13 C nmr光谱比较，将结构分配给其他硫脲的加合物。已开发出一种使用1 H和13 C nmr光谱技术来区分DMAD与胍和am衍生物的加合物可能的结构类型的方法。从各种硫代酰胺和DMAD的产物通过其核磁共振谱和其他光谱进行鉴定。
• Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones
  作者：Jiří Hanusek、Ludmila Hejtmánková、Lenka Kubicová、Miloš Sedlák

  DOI：10.3390/60400323

  日期：——

  Acylation of 2-aminothiobenzamide or 2-methylaminothiobenzamide with substituted benzoyl chlorides has been used to synthesise the corresponding 2-benzoyl-aminothiobenzamides whose subsequent sodium methoxide-catalysed ring closure gives the corresponding quinazoline-4-thiones. These compounds were characterised by means of their 1H- and 13C-NMR spectra. The preferred tautomeric form of selected compounds

  2-氨基硫代苯甲酰胺或 2-甲氨基硫代苯甲酰胺与取代的苯甲酰氯的酰化已被用于合成相应的 2-苯甲酰基-氨基硫代苯甲酰胺，其随后的甲醇钠催化闭环得到相应的喹唑啉-4-硫酮。这些化合物通过它们的 1H-和 13C-NMR 谱进行表征。已根据它们的 13C-NMR、IR 和拉曼光谱讨论了所选化合物的优选互变异构形式。已经发现，在给定的介质中，1-甲基-喹唑啉-4-硫酮的硫取代基被氧取代，得到1-甲基-喹唑啉-4-酮。在强酸介质中，2-苯甲酰氨基硫代苯甲酰胺通过其硫原子环化得到2-苯基苯并[d-1,3]thiazin-4-one。
• Synthesis and Pharmacological Activity of Triazolo[1,5-<i>a</i>]triazine Derivatives Inhibiting Eosinophilia
  作者：Fumihiko Akahoshi、Shinji Takeda、Takehiro Okada、Masahiko Kajii、Hiroko Nishimura、Masanori Sugiura、Yoshihisa Inoue、Chikara Fukaya、Youichiro Naito、Takashi Imagawa、Norifumi Nakamura

  DOI：10.1021/jm970759u

  日期：1998.7.1

  )thiocarbonyl]-1H-1,2, 4-triazole. In the triazolo[1,5-a]triazine series, 2-(4-chlorophenyl)-6-methyl-1,2,4-triazolo[1,5-a]-1,3, 5-triazine-7(6H)-thione (3h) was highly potent, and when given orally it had an ID50 value of 0.3 mg/kg, which is comparable to that of GCC-AP0341. The fact that the structure-activity relationship of these two series was quite similar suggests that a common substructure

  在继续我们先前关于嗜酸性粒细胞增多抑制剂的工作时，我们合成了另外一系列抑制剂，包括5-氨基-1-[[（甲基氨基）硫代羰基] -1H-1,2,4-三唑衍生物和一系列新开发的抑制剂。 1,2,4-三唑并[1,5-a] -1,3,5-三嗪衍生物。我们评估了它们对气道嗜酸性粒细胞模型的抑制活性，该模型是通过静脉内（iv）注射Sephadex颗粒诱导的。在三唑环的3位带有多个取代基的1,2,4-三唑系列中，例如2-呋喃基，吡啶基和苯氧基，没有一种衍生物具有与先前报道的化合物GCC-AP0341相当的活性，即5-氨基-3-（4-氯苯基）-1-[（甲基氨基）硫代羰基] -1H-1,2，4-三唑。在三唑并[1,5-a]三嗪系列中，2-（4-氯苯基）-6-甲基-1,2,4-三唑并[1,5-a] -1,3，5-三嗪-7（6H）-硫酮（3h）具有很高的效力，口服时ID50值为0.3 mg / kg，与GCC-A
• 一种硫代苯甲酰衍生物及其应用
  申请人：沈阳化工研究院有限公司

  公开号：CN112876420B

  公开（公告）日：2023-01-24

  本发明属化学领域，具体的说是一种硫代苯甲酰衍生物，及所述衍生物在治疗癌症、炎症或免疫系统疾病的应用。硫代苯甲酰衍生物结构如通式I所示；式中各取代基的定义见说明书。本发明的化合物可用于治疗癌症疾病。
• Shinde; Shenoy; Pai, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 8, p. 711 - 720
  作者：Shinde、Shenoy、Pai

  DOI：——

  日期：——

表征谱图