acetoxybenzoyl isothiocyanate | 1232634-50-2

• 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: acetoxybenzoyl isothiocyanate
• 英文别名: (2-Carbonisothiocyanatidoylphenyl) acetate
• CAS: 1232634-50-2
• 化学式: C₁₀H₇NO₃S
• 分子量: 221.236
• InChiKey: RZBCVLCCLVALHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  87.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acetoxybenzoyl isothiocyanate 、 2-溴苯胺 以 丙酮 为溶剂， 反应 24.0h， 以34.7%的产率得到2-(((2-bromophenyl)carbamothioyl)carbamoyl)phenyl acetate
  参考文献：
  名称：

  In vitro cytotoxicity evaluation of thiourea derivatives bearing Salix sp. constituent against HK-1 cell lines

  摘要：

  In searching for drugs from natural product scaffolds has gained interest among researchers. In this study, a series of twelve halogenated thiourea (ATX 1-12) via chemical modification of aspirin (a natural product derivative) and evaluated for cytotoxic activity against nasopharyngeal carcinoma (NPC) cell lines, HK-1 via MTS-based colorimetric assay. The cytotoxicity studies demonstrated that halogens at meta position of ATX showed promising activity against HK-1 cells (IC50 value <= 15 mu M) in comparison to cisplatin, a positive cytotoxic drug (IC50 value =8.9 +/- 1.9 mu M). ATX 11, bearing iodine at meta position, showed robust cytotoxicity against HK-1 cells with an IC50 value of 4.7 +/- 0.7 mu M. Molecular docking interactions between ATX 11 and cyclooxygenase-2 demonstrated a robust binding affinity value of -8.1 kcal/mol as compared to aspirin's binding affinity value of -6.4 kcal/mol. The findings represent a promising lead molecule from natural product with excellent cytotoxic activity against NPC cell lines.

  DOI：

  10.1080/14786419.2018.1517120
• 作为产物：
  描述：

  阿司匹林 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.0h， 生成 acetoxybenzoyl isothiocyanate
  参考文献：
  名称：

  含有烷基化胺的新型合成单硫脲阿司匹林衍生物作为潜在的抗菌剂

  摘要：

  通过异硫氰酸酯与一系列苯胺衍生物反应合成了一系列带有烷基化胺部分 1-12 的新阿司匹林，总产率为 16-56%。使用元素分析、FTIR 以及 1H 和 13C NMR 光谱证实了所有合成化合物的拟议结构。通过比浊动力学和柯比鲍尔圆盘扩散法评估所有化合物对大肠杆菌和金黄色葡萄球菌的抗菌活性。与邻位和对位取代基相比，带有间位 CH3 取代基的化合物 5 对受试细菌显示出最高的相对抑菌圈直径。此外，带有较短链的阿司匹林衍生物比较长的烷基链表现出更好的细菌抑制作用。

  DOI：

  10.1155/2017/2378186

文献信息

• Synthesis and In Vitro Anticancer Activity of Novel 2-((3-thioureido)carbonyl) phenyl Acetate Derivatives
  作者：Lin Xiong、Ya-Qin Gao、Chu-E Niu、Hong-Bo Wang、Wei-Hong Li

  DOI：10.2174/15701808113106660075

  日期：2013.12.31

  Novel simplified Aspirin derivatives were developed, characterized by using IR, 1H NMR, 13C NMR and elemental analysis techniques and evaluated for anticancer activity in human cell lines. The results revealed that most of the compounds exhibited inhibitory effects of growth of cancer cell lines in vitro against T-acute lymphoblastic leukemia cell lines Molt-4, chronic myclogenous leukemia cell lines K-562, acute myelocytic leukemia cells lines HL-60, human breast cancer cell lines MCF-7, human hepatic carcinoma cell lines HepG-2 and human lung cancer cell lines A-549. It was observed that some of these compounds exhibited significant anticancer activity particularly 5i which had stronger antileukemia activity with IC50 values ranging from 11.12 to 19.25 µmol·L-1 against 3 leukemia cells than control fluorouracil, so some of the compounds may constitute a novel class of anticancer medicines, which deserves further study.

  新简化的阿司匹林衍生物被开发出来，通过使用红外光谱、核磁共振氢谱、碳谱和元素分析技术进行表征，并在人癌细胞系中评估了其抗癌活性。结果显示，大部分化合物对体外T-急性淋巴母细胞白血病细胞系Molt-4、慢性髓性白血病细胞系K-562、急性髓细胞白血病细胞系HL-60、人乳腺癌细胞系MCF-7、人肝癌细胞系HepG-2和人肺癌细胞系A-549表现出生长抑制效应。观察到其中一些化合物，特别是5i，显示出显著的抗癌活性，其对三种白血病细胞的IC50值在11.12至19.25 µmol·L-1之间，抗白血病活性强于对照药物氟尿嘧啶。因此，这些化合物可能构成一类新型的抗癌药物，值得进一步研究。
• Synthesis and Antibacterial Activity of Acetoxybenzoyl Thioureas with Aryl and Amino Acid Side Chains
  作者：Zainab Ngaini、Maya Asyikin Mohd Arif、Hasnain Hussain、Er Su Mei、Donna Tang、Dyg Halimatulzahrah Abang Kamaluddin

  DOI：10.1080/10426507.2011.562398

  日期：2012.1.1

  Abstract A series of acetoxybenzoylthioureas derivatives with aryl and amino acid ester side chains were prepared by reaction of acetoxybenzoyl isothiocyanate, an acyloxy benzyl ester-based derivative of aspirin, with aryl amines or amino-functionalized amino acids with overall yields of 46–73%. The products that display a thiourea segment as a linker showed improved antibacterial properties in comparison

  摘要 通过乙酰氧基苯甲酰异硫氰酸酯（一种基于阿司匹林的酰氧基苄酯衍生物）与芳胺或氨基官能化氨基酸反应，制备了一系列具有芳基和氨基酸酯侧链的乙酰氧基苯甲酰硫脲衍生物，总产率为 46-73%。与阿司匹林相比，显示硫脲片段作为接头的产品显示出更好的抗菌性能。合成化合物的结构通过红外光谱、 13 C 核磁共振 (NMR) 和 1 H NMR 光谱表征。通过使用革兰氏阴性菌（大肠杆菌 ATCC 8739）筛选化合物的抗菌活性。[2-(苯基氨基甲硫酰基氨基甲酰基)苯基]乙酸酯与其他合成化合物相比，对大肠杆菌的抗菌活性最高。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• Synthesis and structure–activity relationship studies of mono- and <i>bis</i>-thiourea derivatives featuring halogenated azo dyes with antimicrobial properties
  作者：Zainab Ngaini、Ainaa Nadiah Abd Halim、Ferlicia Rasin、Wan Sharifatun Handayani Wan Zullkiplee

  DOI：10.1080/10426507.2022.2046577

  日期：2022.9.2

  Abstract A series of mono-substituted thiourea (2a–i) and bis-substituted thiourea-azo (3a–f) derived from paracetamol derivatives were prepared from isothiocyanates with one and two equivalents of halogenated azo dyes, respectively. The incorporation of azo-derived paracetamol via thiourea moiety in 2a–i depicted excellent microbial activity on Staphylococcus aureus, and 2-(((3-((2-bromophenyl)di

  摘要 由对乙酰氨基酚衍生物衍生的一系列单取代硫脲 ( 2a-i ) 和双取代硫脲-偶氮 ( 3a-f)分别由异硫氰酸酯与一当量和二当量卤化偶氮染料制备。在2a-i中通过硫脲部分引入偶氮衍生的对乙酰氨基酚，描绘了对金黄色葡萄球菌和 2-(((3-((2-溴苯基)二氮烯基)-4-羟苯基)氨基甲硫酰基)氨基甲酰基)苯乙酸酯的优异微生物活性，图 2a显示了与标准氨苄青霉素 (10 mm) 等效的抑制特性。2a的构效关系研究得到了支持与阿司匹林 (-6.4 kcal/mol) 相比，与金黄色葡萄球菌酪氨酰-tRNA 合成酶蛋白的分子对接相互作用显示出 -7.7 kcal/mol 的自由能相互作用。
• Efficient synthesis of new (R)-2-amino-1-butanol derived ureas, thioureas and acylthioureas and in vitro evaluation of their antimycobacterial activity
  作者：Georgi M. Dobrikov、Violeta Valcheva、Yana Nikolova、Iva Ugrinova、Evdokia Pasheva、Vladimir Dimitrov

  DOI：10.1016/j.ejmech.2013.02.034

  日期：2013.5

  The synthesis of 22 structurally diverse urea, thiourea and acylthiourea derivatives containing the (R)-2-amino-1-butanol motif has been performed. The evaluation of their in vitro activity against Mycobacterium tuberculosis (H(37)Rv and strain 43) showed promising results in the case of the acylthiourea derivatives (MIC range 0.36-7.46 mu M for H(37)Rv strain). (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis and molecular design of mono aspirinate thiourea-azo hybrid molecules as potential antibacterial agents
  作者：Zainab Ngaini、Ferlicia Rasin、Wan Sharifatun H. Wan Zullkiplee、Ainaa Nadiah Abd Halim

  DOI：10.1080/10426507.2020.1828885

  日期：2021.3.4

  New mono aspirinate thiourea-azo derivatives2a-fwere synthesized using aspirin as a natural product-based precursor, with 4-aminophenylazophenol derivatives in excellent 70-90% yields. Overall,2a-fgave excellent antibacterial activity againstStaphylococcus aureusS48/81 and 2-(((3-((2-bromophenyl)diazenyl)-4-hydroxyphenyl)carbamothioyl)carbamoyl)phenyl acetate(2d)exhibited a larger zone of inhibition 10 mm, comparable to the standard ampicillin. The molecular docking analysis of2dagainstS. aureustyrosyl-tRNA synthetase protein displayed a free energy interaction of -7.7 kcal/mol compared to aspirin (-6.4 kcal/mol).