1,3-di-1-naphthoylimidazolidine-2-thione | 1146942-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-di-1-naphthoylimidazolidine-2-thione
• 英文别名: [3-(Naphthalene-1-carbonyl)-2-sulfanylideneimidazolidin-1-yl]-naphthalen-1-ylmethanone
• CAS: 1146942-66-6
• 化学式: C₂₅H₁₈N₂O₂S
• 分子量: 410.496
• InChiKey: GTTXQKHSTUKWDM-UHFFFAOYSA-N

物化性质

• 熔点：
  189-191 °C(Solvent: Dichloromethane; Diethyl ether)
• 沸点：
  609.7±38.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  亚乙基硫脲 、 1-萘甲酰氯 在 吡啶 作用下， 反应 0.5h， 以68%的产率得到1,3-di-1-naphthoylimidazolidine-2-thione
  参考文献：
  名称：

  N-Acylated and N,N′-diacylated imidazolidine-2-thione derivatives and N,N′-diacylated tetrahydropyrimidine-2(1H)-thione analogues: Synthesis and antiproliferative activity

  摘要：

  Fifty-one acylthioureas (ATUs) incorporating imidazolidine-2-thione or its upper cyclohomologue were prepared by parallel synthesis and evaluated against a high number of human cancer cell lines for antiproliferative activity. ATUs 1o (3,5-dichlorobenzoyl), 1s (2-furoyl), 3s (2-furoyl) and 1t (2-thenoyl) displayed activity against leukemia, melanoma LOX IMVI, non-small cell lung NCI-H522, renal 786-0, CAKI-1, SN12C, UO-31 and breast MCF7, MDA-MB-435, T-47D cancer cell lines in the 0.3-9.7 mu M concentration range. Compound 14s exhibited selectivity for melanoma SK-MEL-5 (GI(50) < 5 nM); 1s for leukemia MOLT-4 (GI(50): 300 nM); 1q, 3b and 3q for renal cancer UO-31 (GI(50): 70200 nM); 8s, 9s for non-small cell lung cancer EKVX (GI(50): 300, 10 nM) and 3j for HOP-92 (GI(50): 700 nM) cell line. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.06.010

文献信息

• N-Acylated and N,N′-diacylated imidazolidine-2-thione derivatives and N,N′-diacylated tetrahydropyrimidine-2(1H)-thione analogues: Synthesis and antiproliferative activity
  作者：Sara Cesarini、Andrea Spallarossa、Angelo Ranise、Silvia Schenone、Camillo Rosano、Paolo La Colla、Giuseppina Sanna、Bernardetta Busonera、Roberta Loddo

  DOI：10.1016/j.ejmech.2008.06.010

  日期：2009.3

  Fifty-one acylthioureas (ATUs) incorporating imidazolidine-2-thione or its upper cyclohomologue were prepared by parallel synthesis and evaluated against a high number of human cancer cell lines for antiproliferative activity. ATUs 1o (3,5-dichlorobenzoyl), 1s (2-furoyl), 3s (2-furoyl) and 1t (2-thenoyl) displayed activity against leukemia, melanoma LOX IMVI, non-small cell lung NCI-H522, renal 786-0, CAKI-1, SN12C, UO-31 and breast MCF7, MDA-MB-435, T-47D cancer cell lines in the 0.3-9.7 mu M concentration range. Compound 14s exhibited selectivity for melanoma SK-MEL-5 (GI(50) < 5 nM); 1s for leukemia MOLT-4 (GI(50): 300 nM); 1q, 3b and 3q for renal cancer UO-31 (GI(50): 70200 nM); 8s, 9s for non-small cell lung cancer EKVX (GI(50): 300, 10 nM) and 3j for HOP-92 (GI(50): 700 nM) cell line. (C) 2008 Elsevier Masson SAS. All rights reserved.