4-(isothiocyanatomethyl)benzoic acid | 35009-14-4

• 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: 4-(isothiocyanatomethyl)benzoic acid
• CAS: 35009-14-4
• 化学式: C₉H₇NO₂S
• 分子量: 193.226
• InChiKey: YJHAFHMZBVQRFC-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  377.1±25.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(isothiocyanatomethyl)benzoic acid 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 37.5h， 生成 (R)-tert-butyl N-(2-(4-((3-(2-hydroxy-2-phenylethyl)thioureido)methyl)benzamido)phenyl)carbamate
  参考文献：
  名称：

  Potent and Selective Inhibitors of Histone Deacetylase-3 Containing Chiral Oxazoline Capping Groups and a N-(2-Aminophenyl)-benzamide Binding Unit

  摘要：

  A novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contains an oxazoline capping group and a N-(2-aminophenyl)-benzamide unit. Among several new inhibitors of this type exhibiting Class I selectivity and potent inhibition of HDAC3-NCoR2, in vitro assays for the inhibition of HDAC1, HDAC2, and HDAC3-NCoR2 by N-(2-aminophenyl)-benzamide 15k gave respective IC50 values of 80, 110, and 6 nM. Weak inhibition of all other HDAC isoforms (HDAC4, 5, 6, 7, and 9: IC50 > 100 000 nM; HDAC8: IC50 = 25 000 nM; HDAC10: IC50 > 4000 nM; HDAC11: IC50 > 2000 nM) confirmed the Class I selectivity of 15k 2-Aminoimidazolinyl, 2-thioimidazolinyl, and 2-aminooxazolinyl units were shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl)-benzamides previously reported, but the 2-aminooxazolinyl unit was the most potent in inhibiting HDAC3-NCoR2. Many of the new HDAC inhibitors showed higher solubilities and lower binding to human serum albumin than that of Mocetinostat. Increases in histone H3K9 acetylation in the human cell lines U937 and PC-3 was observed for all three oxazolinyl inhibitors evaluated; those HDAC inhibitors also lowered cyclin E expression in U937 cells but not in PC-3 cells, indicating underlying differences in the mechanisms of action of the inhibitors on those two cell lines.

  DOI：

  10.1021/acs.jmedchem.5b00545
• 作为产物：
  描述：

  二硫化碳 、 4-氨甲基苯甲酸 在 三乙胺 、 碘 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 26.07h， 生成 4-(isothiocyanatomethyl)benzoic acid
  参考文献：
  名称：

  EP2248800

  摘要：

  公开号：

文献信息

• Facile synthesis of aliphatic isothiocyanates and thioureas on solid phase using peptide coupling reagents
  作者：Ulrik Boas、Heidi Gertz、Jørn B. Christensen、Peter M.H. Heegaard

  DOI：10.1016/j.tetlet.2003.10.182

  日期：2004.1

  Peptide coupling reagents can be used as versatile reagents for the formation of aliphatic isothiocyanates and thioureas on solid phase from the corresponding solid-phase anchored aliphatic primary amines. The formation of the thioureas is fast and highly chemoselective, and proceeds via formation of the intermediate isothiocyanate. The isothiocyanate and subsequent thiourea formation take place under

  肽偶联剂可用作通用试剂，用于由相应的固相锚定的脂族伯胺在固相上形成脂族异硫氰酸酯和硫脲。硫脲的形成是快速且高度化学选择性的，并且通过中间体异硫氰酸酯的形成而进行。异硫氰酸酯和随后的硫脲的形成在标准肽偶联条件下进行，使用二硫化碳作为“氨基酸”。硫脲从树脂中释放出来，并以中等至高收率分离。
• Process for preparing peptide derivatized oligomeric compounds
  申请人：——

  公开号：US20020156235A1

  公开（公告）日：2002-10-24

  Methods of preparing peptide linked oligomeric compounds are provided. The method is useful for preparing larger scale amounts of peptide linked oligomeric compounds. More particularly, the synthesis of peptide linked oligomeric compounds is performed without the problems of aggregation associated with electrostatic interactions. The present method describes using equimolar amounts of oligomeric compounds and peptide reagents providing for an increase in overall efficiency.

  提供了制备肽链寡聚化合物的方法。该方法适用于制备规模较大的肽链寡聚化合物。更具体地说，肽链寡聚化合物的合成是在没有与静电相互作用有关的聚集问题的情况下进行的。本方法描述了使用等摩尔量的寡聚化合物和肽试剂，从而提高了整体效率。
• Method for producing isothiocyanate compound having carboxyl group
  申请人：Nakano Satoshi

  公开号：US08367857B2

  公开（公告）日：2013-02-05

  To provide a novel method for producing an isothiocyanate compound having a carboxyl group(s) from the corresponding amino compound having a carboxyl group(s). A method for producing an isothiocyanate compound which has a carboxyl group(s) and is represented by the formula (2). And the method comprises reacting an amino compound which has a carboxyl group(s) and is represented by the formula (1) (wherein A is e.g. a C6-14 aromatic hydrocarbon group or a C1-12 saturated hydrocarbon group, and B is e.g. a single bond, a C6-14 aromatic hydrocarbon group or a C1-12 saturated hydrocarbon group), in a solvent, with carbon disulfide (CS2) and then with a halogen as a simple substance.

  提供一种从具有羧基的相应氨基化合物中产生具有羧基的异硫氰酸酯化合物的新方法。一种产生具有羧基的异硫氰酸酯化合物的方法，该化合物由公式（2）表示。该方法包括在溶剂中反应具有羧基的氨基化合物，该氨基化合物由公式（1）表示（其中A为例如C6-14芳香烃基或C1-12饱和烃基，B为例如单键，C6-14芳香烃基或C1-12饱和烃基），然后与二硫化碳（CS2）和卤素作为简单物质反应。
• METHOD FOR PRODUCING ISOTHIOCYANATE COMPOUND HAVING CARBOXYL GROUP
  申请人：Nakano Satoshi

  公开号：US20100312000A1

  公开（公告）日：2010-12-09

  To provide a novel method for producing an isothiocyanate compound having a carboxyl group(s) from the corresponding amino compound having a carboxyl group(s). A method for producing an isothiocyanate compound which has a carboxyl group(s) and is represented by the formula (2). And the method comprises reacting an amino compound which has a carboxyl group(s) and is represented by the formula (1) (wherein A is e.g. a C 6-14 aromatic hydrocarbon group or a C 1-12 saturated hydrocarbon group, and B is e.g. a single bond, a C 6-14 aromatic hydrocarbon group or a C 1-12 saturated hydrocarbon group), in a solvent, with carbon disulfide (CS2) and then with a halogen as a simple substance.

  提供一种新的方法，用于从具有羧基（s）的相应氨基化合物制备具有羧基（s）的异硫氰酸酯化合物。一种用于生产具有羧基（s）的异硫氰酸酯化合物的方法，其表示为公式（2）。该方法包括在溶剂中反应具有羧基（s）的氨基化合物，其表示为公式（1）（其中A是例如C6-14芳香族碳氢基团或C1-12饱和碳氢基团，B是例如单键，C6-14芳香族碳氢基团或C1-12饱和碳氢基团），与二硫化碳（CS2）然后与卤素作为简单物质。
• Grabenko,A.D. et al., Journal of Organic Chemistry USSR (English Translation), 1972, vol. 8, p. 532 - 534
  作者：Grabenko,A.D. et al.

  DOI：——

  日期：——