N-[(5-溴-2-吡啶基)硫代氨基甲酰]苯甲酰胺 | 31430-37-2

• 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: N-[(5-溴-2-吡啶基)硫代氨基甲酰]苯甲酰胺
• 英文名称: N-benzoyl-N'-(5-bromo-2-pyridyl)thiourea
• 英文别名: N-(5'-bromo-2'-pyridyl)-N'-benzoylthiourea；1-benzoyl-3-(5-bromo-pyridin-2-yl)-thiourea；N-[(5-bromopyridin-2-yl)carbamothioyl]benzamide
• CAS: 31430-37-2
• 化学式: C₁₃H₁₀BrN₃OS
• 分子量: 336.212
• InChiKey: GWFCYWAONSDFIU-UHFFFAOYSA-N

物化性质

• 熔点：
  164-168 °C
• 密度：
  1.616±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  N-[(5-溴-2-吡啶基)硫代氨基甲酰]苯甲酰胺 在 sodium hydroxide 作用下， 生成 1-(5-溴-2-吡啶基)-2-硫脲
  参考文献：
  名称：

  Identification of 2-amino-5-(thioaryl)thiazoles as inhibitors of nerve growth factor receptor TrkA

  摘要：

  2-Amino-5-(thioaryl)thiazoles are potent inhibitors of TrkA (e.g., 20h, TrkA IC50 = 0.6 nM) that show anti-proliferative effect in cellular assays. A proposed inhibitor binding mode to TrkA active site is consistent with key SAR observations. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.076
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 、 苯甲酰基异硫氰酸酯 以 乙醇 为溶剂， 反应 0.25h， 生成 N-[(5-溴-2-吡啶基)硫代氨基甲酰]苯甲酰胺
  参考文献：
  名称：

  正甲基和正苯甲酰基吡啶基硫脲的氧化环化。新型噻唑并[4,5- b ]和[5,4- b ]吡啶衍生物的制备

  摘要：

  由相应的氨基吡啶-吡啶制备的N-甲基和N-苯甲酰基吡啶基硫脲的环化已经使用各种条件实现。用溴在乙酸或铁氰化钾中的环化反应在吡啶环的氮上进行，得到吡啶鎓盐或1,2,4-噻二唑并[2,3- a ]吡啶亚砜体系。另一方面，在N-甲基吡咯烷酮（NMP）中用甲醇钠处理硫脲导致导致噻唑并[4,5- b ]和[5,4- b ]吡啶的形成，这是生物学评估中令人关注的目标。

  DOI：

  10.1002/jhet.5570400210

文献信息

• Oxidative cyclization of<i>n</i>-methyl- and<i>n</i>-benzoylpyridylthioureas. Preparation of new thiazolo[4,5-<i>b</i>] and [5,4-<i>b</i>] pyridine derivatives
  作者：Karine Jouve、Jan Bergman

  DOI：10.1002/jhet.5570400210

  日期：2003.3

  Cyclization of N-methyl- and N-benzoylpyridylthioureas, prepared from the corresponding aminopy-ridines, has been realized using various conditions. With bromine in acetic acid or potassium ferricyanide, the cyclization occurred on the nitrogen of the pyridine ring and pyridinium salts or 1,2,4-fhiadiazolo[2,3-a]pyridylidene systems were obtained. On the other hand, treatment of the thioureas with

  由相应的氨基吡啶-吡啶制备的N-甲基和N-苯甲酰基吡啶基硫脲的环化已经使用各种条件实现。用溴在乙酸或铁氰化钾中的环化反应在吡啶环的氮上进行，得到吡啶鎓盐或1,2,4-噻二唑并[2,3- a ]吡啶亚砜体系。另一方面，在N-甲基吡咯烷酮（NMP）中用甲醇钠处理硫脲导致导致噻唑并[4,5- b ]和[5,4- b ]吡啶的形成，这是生物学评估中令人关注的目标。
• The first synthesis of pyridinium N-benzoylguanidines by bismuth- and mercury-promoted guanylation of N-iminopyridinium ylide with thioureas
  作者：Silvio Cunha、Manoel T. Rodrigues、Cleuza C. da Silva、Hamilton B. Napolitano、Ivo Vencato、Carlito Lariucci

  DOI：10.1016/j.tet.2005.08.052

  日期：2005.10

  This work describes the first successful synthesis of five pyridinium N-benzoylguanidines. These new pyridinium ylides were prepared in moderate to good yields through the guanylation reaction of N-iminopyridinium ylide with N-benzoylthioureas, using both bismuth nitrate and mercury chloride as inorganic thiophiles. X-ray analysis of one pyridinium N-benzoylguanidine was investigated and the E configuration

  这项工作描述了五个吡啶N-苯甲酰胍的首次成功合成。通过的脒化反应在中等至良好的产率制备这些新的吡啶鎓叶立德Ñ -iminopyridinium叶立德与Ñ -benzoylthioureas，同时使用硝酸铋和氯化汞作为无机thiophiles。研究了一种吡啶鎓N-苯甲酰胍的X射线分析，并确定了E构型。在固态下观察到C–H⋯O和C–H⋯π型的分子间相互作用。这项研究中相关的结果代表了叶立德在鸟苷酸化反应中作为亲核伴侣的首次描述。
• Antimicrobial Activity and Structural Study of Disubstituted Thiourea Derivatives
  作者：Silvio Cunha、Fernando C. Macedo、Giselle A. N. Costa、Manoel T. Rodrigues、Rosival B. V. Verde、Lourdes C. de Souza Neta、Ivo Vencato、Carlito Lariucci、Fernando P. Sá

  DOI：10.1007/s00706-007-0600-y

  日期：2007.5

  The antimicrobial activity of six N-phenyl- and fourteen N-benzoylthiourea derivatives were evaluated from their Minimal Inhibitory Concentration (MIC) values using the microdilution procedure against ten microorganisms. Most of the compounds exhibited selective activity against fungi and Gram-positive bacteria, which were very effectively inhibited by some of the tested thioureas. Additionally, SAR considerations and four novel X-ray diffraction structures of N-benzoylthioureas are included.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Rh: SVol.B3, 1.1.4.3.2, page 11 - 11
  作者：

  DOI：——

  日期：——
• Shome, S. C.; Mazumdar, M.; Haldar, P. K., Journal of the Indian Chemical Society, 1977, vol. 54, p. 947 - 950
  作者：Shome, S. C.、Mazumdar, M.、Haldar, P. K.、Das, D. K.

  DOI：——

  日期：——