N-benzoyl-N'-(5-chloro-2-pyridyl)thiourea | 31430-26-9

• 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: N-benzoyl-N'-(5-chloro-2-pyridyl)thiourea
• 英文别名: 5-chloropyridyl-N′-benzoylthiourea；1-benzoyl-3-(5-chloro-pyridin-2-yl)-thiourea；N-[(5-chloropyridin-2-yl)carbamothioyl]benzamide
• CAS: 31430-26-9
• 化学式: C₁₃H₁₀ClN₃OS
• 分子量: 291.761
• InChiKey: TXOIIYZNZLUFJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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

反应信息

• 作为反应物：
  描述：

  N-benzoyl-N'-(5-chloro-2-pyridyl)thiourea 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (5-氯吡啶-2-基)硫脲
  参考文献：
  名称：

  Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against Klebsiella pneumoniae

  摘要：

  一系列融合的双环2-氨基噻唑基化合物被合成并评估其与多粘菌素B（PB）对抗肺炎克雷伯菌（SIPI-KPN-1712）的协同效应。

  DOI：

  10.1039/c7md00354d
• 作为产物：
  描述：

  苯甲酰氯 以 乙酸乙酯 、 丙酮 为溶剂， 反应 3.0h， 生成 N-benzoyl-N'-(5-chloro-2-pyridyl)thiourea
  参考文献：
  名称：

  Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against Klebsiella pneumoniae

  摘要：

  一系列融合的双环2-氨基噻唑基化合物被合成并评估其与多粘菌素B（PB）对抗肺炎克雷伯菌（SIPI-KPN-1712）的协同效应。

  DOI：

  10.1039/c7md00354d

文献信息

• Synthesis and spectroscopic properties of some new<i>N,N'</i>-disubstituted thiorueas of potential biological interest
  作者：George Y. Sarkis、Essam D. Faisal

  DOI：10.1002/jhet.5570220134

  日期：1985.1

  Thirty-six new N,N'-disubstituted thioureas have been synthesized by the reaction of phenyl-, p-fluorophenyl- and benzoylisothiocyanates with various substituted anilines, aminopyridines and 4-aminoquinolines. The uv, ir and nmr spectral data are presented and discussed.

  通过使苯基，对氟苯基和苯甲酰基异硫氰酸酯与各种取代的苯胺，氨基吡啶和4-氨基喹啉反应，已经合成了三十六种新的N，N′-二取代的硫脲。介绍并讨论了uv，ir和nmr光谱数据。
• Synthesis and spectral characterization of some new<i>N</i>-substituted 2-aminobenzothiazoles, 2-aminothiazolopyridines and 2-aminothiazoloquinolines
  作者：George Y. Sarkis、Essam D. Faisal

  DOI：10.1002/jhet.5570220322

  日期：1985.5

  A series of N-substituted 2-aminobenzothiazoles, 2-aminothiazolopyridines, and 2-aminothiazoloquinolines were prepared by the cyclization of N,N'-disubstituted thiourea derivatives by bromine in acetic acid. The uv, ir and nmr data for these compounds are presented and discussed.

  通过在乙酸中用溴将N，N′-二取代的硫脲衍生物环化，制备了一系列N-取代的2-氨基苯并噻唑，2-氨基噻唑并吡啶和2-氨基噻唑并喹啉。介绍并讨论了这些化合物的uv，ir和nmr数据。
• Antitumor activity of Pd(II) complexes with N,S or O,S coordination modes of acylthiourea ligands
  作者：Ana M. Plutín、Raúl Ramos、Raúl Mocelo、Anislay Alvarez、Eduardo E. Castellano、Marcia R. Cominetti、Katia M. Oliveira、Tamires Donizeth de Oliveira、Thales E.M. Silva、Rodrigo S. Correa、Alzir A. Batista

  DOI：10.1016/j.poly.2020.114543

  日期：2020.7

  determined by X-ray crystallography. The present study reports on an interesting contribution on the chemistry of Pd(II)/acylthiourea complexes, where the use of monosubstituted acylthiourea conducts to formation of neutral complexes with general formula [Pd(Cl)(PPh3)(acylthiourea)], with a N,S-coordination mode. On the other hand, cationic complexes with formula [Pd(PPh3)2(acylthiourea)]+, with O,S bidentately

  摘要制备了7种新的Pd（II）与N-烷基和N，N-二烷基-N'-酰基硫脲的配合物（1–7），并通过元素分析和光谱技术对其进行了表征。配位化合物[PdCl（PPh3）（5-cloropiridyl-N'-苯甲酰硫脲-k2N，S）]（2），顺式[Pd（PPh3）2（N-吗啉-N'-苯甲酰硫脲-k2O）的晶体结构，S）] PF 6（4）和顺式-[Pd（PPh 3）2（N，N-二苯基-N'-硫代苯基硫脲基-k 2 O，S）] PF 6（7）通过X射线晶体学测定。本研究报告了对Pd（II）/酰基硫脲配合物化学的有趣贡献，其中单取代的酰基硫脲的使用可形成通式为[Pd（Cl）（PPh3）（酰基硫脲）]的中性配合物，其中N，S协调模式。另一方面，式为[Pd（PPh3）2（酰基硫脲）] +的阳离子配合物，带有O，通过使用二取代的酰基硫脲衍生物获得与金属二齿配位的S。针对DU-145肿瘤细胞（前列腺癌细胞）的
• 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。
• Structure–activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis
  作者：Anja Meissner、Helena I. Boshoff、Mahalakshmi Vasan、Benjamin P. Duckworth、Clifton E. Barry、Courtney C. Aldrich

  DOI：10.1016/j.bmc.2013.08.048

  日期：2013.11

  A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl)-1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 mu M or 0.008 mu g/mL in 7H9 media and therapeutic index of nearly similar to 300. However, 55 is rapidly metabolized by human liver microsomes (t(1/2) = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of similar to 10 (5). (C) 2013 Elsevier Ltd. All rights reserved.