N-(phenylpropionyl)benzoxazoline-2-thione | 312313-34-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: N-(phenylpropionyl)benzoxazoline-2-thione
• 英文别名: N-(2-Phenylpropanoyl)benzoxazole-2-thione；3-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)propan-1-one；3-Phenyl-1-(2-sulfanylidene-1,3-benzoxazol-3-yl)propan-1-one
• CAS: 312313-34-1
• 化学式: C₁₆H₁₃NO₂S
• 分子量: 283.351
• InChiKey: HPSACBAWQPSJCV-UHFFFAOYSA-N

物化性质

• 沸点：
  432.6±38.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(phenylpropionyl)benzoxazoline-2-thione 在 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 1.25h， 生成 2-[(3,3,4,4-tetramethylthietan-2-ylidene)amino]phenyl acetate
  参考文献：
  名称：

  N-酰基苯并恶唑-2-硫酮的光化学反应

  摘要：

  研究了N-酰基苯并恶唑-2-硫酮1的光化学反应。在多种存在下辐照N-酰基苯并恶唑-2-硫酮1烯烃 2产生2取代苯并恶唑 3–20和/或意想不到的产物，通过分子内诱捕亚氨基噻吨21–29酰基 经过 硫醇根阴离子两性离子中间体I和酚盐阴离子分别由区域选择性形成的螺环氨基硫杂环丁烷AT衍生的两性离子中间体II[2 + 2]环加成的碳硫双键1与烯烃 双键。

  DOI：

  10.1039/b002548h
• 作为产物：
  描述：

  2-巯基苯并恶唑 、 3-苯丙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以35%的产率得到N-(phenylpropionyl)benzoxazoline-2-thione
  参考文献：
  名称：

  Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase

  摘要：

  Bacterial hyaluronan lyases (Hyal) degrade hyaluronan, an important component of the extracellular matrix, and are involved in microbial spread. Hyal inhibitors may serve as tools to study the role of the enzyme, its substrates and products in the course of bacterial infections. Moreover, such enzyme inhibitors are potential candidates for antibacterial combination therapy. Based on crystal structures of Streptococcus pneumoniae Hyal in complex with a hexasaccharide substrate and with different inhibitors, 1-acylated benzimidazole-2-thiones and benzoxazole-2-thiones were derived as new leads for the inhibition of Streptococcus agalactiae strain 4755 Hyal. Structure-based optimization led to N-(3-phenylpropionyl)benzoxazole-2-thione, one of the most potent compounds known to date (IC50 values: 24 mu M at pH 7.4, 15 mu M at pH 5). Among the 27 new derivatives, other N-acylated benzimidazoles and benzoxazoles are just as active at pH 7.4, but not at pH 5. The results support a binding mode characterized by interactions with residues in the catalytic site and with a hydrophobic patch. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.014

文献信息

• Photoaddition Reactions of Benzoxazole-2(3H)-thiones to Cycloalkenes and Heteroaromatics
  作者：Takehiko Nishio、Kiyoko Shiwa、Masami Sakamoto

  DOI：10.1002/hlca.200390266

  日期：2003.10

  cyclohexa-1,4-diene (2d), and indene (2e) yielded 2-substituted benzoxazoles 4–13, 18 and 19, and iminothietanes 14–17, by intramolecular trapping of the acyl or MeOCO and PhOCO groups by thiolate anion of the zwitterionic intermediate I and by the phenolate anion of the zwitterionic intermediate II, respectively, derived from the spirocyclic amino-thietanes AT formed by [2+2] cycloaddition of the CS bond of

  苯并恶唑-2-硫酮的光加成反应1与环烯烃2和杂芳族化合物3进行了检查。的照射Ñ -acylbenzoxazole -2-硫酮1A和1B，和3-（甲氧羰基） -苯并恶唑-2-和3-（苯氧基羰基）（3 ħ）-thiones（1F和1H。，RESP）在环烯烃的存在2A -图2c，环己-1,4-二烯（2D）和茚（2E），得到2-取代的苯并恶唑4 - 13，18和19，和iminothietanes 14- 17，由两性离子中间体的硫醇盐阴离子的酰基或MeOCO和PhOCO基团的分子内俘获我和由两性离子中间体的酚盐阴离子II，分别从螺环氨基thietanes衍生AT通过形成[2 + 2] 1的CS键和2的CC键的环加成。在杂芳族化合物3的存在下照射1只能得到2-取代的苯并恶唑20 – 33。
• Synthesis of Aliphatic Polyamide Dendrimers Based on Facile Convergent Method
  作者：Yumiko Ito、Tomoya Higashihara、Mitsuru Ueda

  DOI：10.1021/ma300735w

  日期：2012.5.22

  A novel and rapid approach for the synthesis of aliphatic polyamide dendrimers, consisting of the 3,4-dialkoxyhydrocinnamamide structure as a repeating unit, has been developed. Aliphatic polyamide dendrons and dendrimers were easily prepared by a convergent approach involving activation of a carboxylic acid at the focal point using (2,3-dihydro-2-thioxo-3-benzoxazolyl)phosphonate (DBOP) as the activating

  已经开发了一种新颖且快速的合成脂肪族聚酰胺树枝状大分子的方法，该方法由3,4-二烷氧基氢肉桂酰胺结构作为重复单元。脂肪族聚酰胺树枝状和树枝状聚合物很容易通过收敛方法制备，包括使用（2,3-二氢-2-硫代羰基-3-苯并恶唑基）膦酸酯（DBOP）作为活化剂在焦点处活化羧酸，然后缩合带有未受保护的AB 2构件。由第三代树突和含有两个或三个官能团的核心分子制备哑铃形和星形的第三代树状聚合物。以上所有产物只能通过沉淀纯化，其结构经1证实。H NMR，IR和基质辅助激光解吸电离飞行时间质谱（MALDI–TOF–MS）的光谱学和元素分析。
• Acylation and Alkoxycarbony-lation of Benzoxazoline-2-thione and Benzothiazoline-2-thione
  作者：Takehiko Nishio、Kiyoko Shiwa

  DOI：10.3987/com-03-s(p)10

  日期：——

  Acylation of benzoxazoline-2-thione (1) and benzothiazoline-2-thione (2) with acetic anhydride (3) and acyl chlorides (4) gave N-acyl (5, 6) and/or S-acyl (7, 8) derivatives depending on the nature of acylating agents and bases used. Alkoxycarbonylation of 1 with aralkyl chlorocarbonates (9) gave N-alkoxycarbonyl derivatives (10) mainly, while that of 2 with aralkyl chloroccarbonates (9) gave S-alkoxycarbonyl derivatives (12) exclusively. Photolysis of N-acyl derivatives (5 or 6) in the presence of alcohols afforded 1 or 2, respectively, together with esters (16).
• Photochemical reactions of N-acylbenzoxazole-2-thiones
  作者：Takehiko Nishio、Ikuo Iida、Kunio Sugiyama

  DOI：10.1039/b002548h

  日期：——

  presence of a variety of alkenes 2 yields 2-substituted benzoxazoles 3–20 and/or the unexpected products, iminothietanes 21–29 by intramolecular trapping of the acyl group by thiolate anion of the zwitterionic intermediate I and by the phenolate anion of the zwitterionic intermediate II, respectively, derived from the spirocyclic aminothietanes AT which are formed by regioselective [2+2] cycloaddition of

  研究了N-酰基苯并恶唑-2-硫酮1的光化学反应。在多种存在下辐照N-酰基苯并恶唑-2-硫酮1烯烃 2产生2取代苯并恶唑 3–20和/或意想不到的产物，通过分子内诱捕亚氨基噻吨21–29酰基 经过 硫醇根阴离子两性离子中间体I和酚盐阴离子分别由区域选择性形成的螺环氨基硫杂环丁烷AT衍生的两性离子中间体II[2 + 2]环加成的碳硫双键1与烯烃 双键。
• Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase
  作者：Stephan Braun、Alexander Botzki、Sunnhild Salmen、Christian Textor、Günther Bernhardt、Stefan Dove、Armin Buschauer

  DOI：10.1016/j.ejmech.2011.07.014

  日期：2011.9

  Bacterial hyaluronan lyases (Hyal) degrade hyaluronan, an important component of the extracellular matrix, and are involved in microbial spread. Hyal inhibitors may serve as tools to study the role of the enzyme, its substrates and products in the course of bacterial infections. Moreover, such enzyme inhibitors are potential candidates for antibacterial combination therapy. Based on crystal structures of Streptococcus pneumoniae Hyal in complex with a hexasaccharide substrate and with different inhibitors, 1-acylated benzimidazole-2-thiones and benzoxazole-2-thiones were derived as new leads for the inhibition of Streptococcus agalactiae strain 4755 Hyal. Structure-based optimization led to N-(3-phenylpropionyl)benzoxazole-2-thione, one of the most potent compounds known to date (IC50 values: 24 mu M at pH 7.4, 15 mu M at pH 5). Among the 27 new derivatives, other N-acylated benzimidazoles and benzoxazoles are just as active at pH 7.4, but not at pH 5. The results support a binding mode characterized by interactions with residues in the catalytic site and with a hydrophobic patch. (C) 2011 Elsevier Masson SAS. All rights reserved.