5-p-Methylbenzylidenisorhodanin | 38675-73-9

• 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: 5-p-Methylbenzylidenisorhodanin
• 英文别名: 5-(4-methyl-benzylidene)-4-thioxo-thiazolidin-2-one；5-[(4-Methylphenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one
• CAS: 38675-73-9
• 化学式: C₁₁H₉NOS₂
• 分子量: 235.331
• InChiKey: HINACWNSVOMORM-UHFFFAOYSA-N

物化性质

• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基肉桂酸 、 5-p-Methylbenzylidenisorhodanin 在 溶剂黄146 、 对苯二酚 作用下， 反应 2.0h， 以69%的产率得到5-(3,4-dimethoxyphenyl)-7-(4-methylphenyl)-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-6-carboxylic acid
  参考文献：
  名称：

  Crotonic, cynnamic, and propiolic acids motifs in the synthesis of thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels–Alder reaction and related tandem processes

  摘要：

  Various novel thiopyrano[2,3-d][1,3]thiazol-2-one-6-carboxylic acids derivatives were synthesized in 54-86% yields via hetero-Diels Alder reactions and related acylation-based tandem processes of 5-arylidene-4-thioxo-2-thiazolidinones with crotonic, propiolic, and cynnamic acids derivatives. Stereo- and regioselectivity of cycloaddition were investigated. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.083
• 作为产物：
  描述：

  5-(4-methylbenzylidene)thiazolidine-2,4-dione 在 tetraphosphorus decasulfide 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-p-Methylbenzylidenisorhodanin
  参考文献：
  名称：

  V'yunov,K.A. et al., Journal of Organic Chemistry USSR (English Translation), 1975, vol. 11, p. 882 - 885

  摘要：

  DOI：

文献信息

• Synthesis and in vivo antidiabetic activity of novel dispiropyrrolidines through [3+2] cycloaddition reactions with thiazolidinedione and rhodanine derivatives
  作者：Ramalingam Murugan、S. Anbazhagan、S. Sriman Narayanan

  DOI：10.1016/j.ejmech.2009.03.035

  日期：2009.8

  reaction with 5-arylidene-1,3-thiazolidine-2,4-dione and 5-arylidene-4-thioxo-1,3-thiazolidine-2-one derivatives as dipolarophiles. The structure and stereochemistry of the cycloadduct have been established by single crystal X-ray structure and spectroscopic techniques. Molecular docking studies were performed on 1FM9 protein. The synthesized compounds were screened for their antidiabetic activity on male

  通过与5-亚芳基-1,3-噻唑烷-2,4-二酮和5-亚芳基-4-硫代-1,3-噻唑烷-的1,3-偶极环加成反应完成了一系列新型双螺并吡咯烷的合成。 2-one衍生物为双极性亲和剂。环加合物的结构和立体化学已经通过单晶X射线结构和光谱技术确定。对1FM9蛋白进行了分子对接研究。筛选合成的化合物对雄性Wistar大鼠的抗糖尿病活性。
• Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-<i>d</i>]thiazoles as potential biologically active compounds
  作者：Andrii Lozynskyi、Borys Zimenkovsky、Ihor Nektegayev、Roman Lesyk

  DOI：10.1515/hc-2014-0204

  日期：2015.2.1

  Novel rel-(5R,6S,7S)-2-oxo-5,7-diaryl-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazol-6-yl-oxo-acetic acids were synthesized in 52–70% yields via regioselective and diastereoselective hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with a series of arylidene pyruvic acids. The synthesized compounds were evaluated for anticancer activity in NCI60 cancer cell lines and for antiexudative activity on the carrageenan edema model in rats. Biological screening data led to identification of 3e as having moderate antitumor activity on the colon cancer HT-29 cell line and of 3b as having promising antiexudative effect.

  新型rel-(5R,6S,7S)-2-氧代-5,7-二芳基-3,5,6,7-四氢-2H-噻吩并[2,3-d]噻唑-6-基-氧代-乙酸在52-70%的产率下通过5-芳基亚亚甲基-4-硫代-2-噻唑烷酮与一系列芳基亚亚甲基丙酮酸的区域选择性和对映选择性异-Diels-Alder反应合成。合成的化合物在NCI60癌细胞系中进行了抗癌活性评价，并在大鼠卡拉胶水肿模型上进行了抗渗出活性评价。生物筛选数据表明3e在结肠癌HT-29细胞系中具有中等抗肿瘤活性，3b具有有希望的抗渗出效果。

• Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids
  作者：Andrii Lozynskyi、Viktoria Zasidko、Dmytro Atamanyuk、Danylo Kaminskyy、Halyna Derkach、Olexandr Karpenko、Volodymyr Ogurtsov、Roman Kutsyk、Roman Lesyk

  DOI：10.1007/s11030-017-9737-8

  日期：2017.5

  AbstractHere it is described the synthesis, antioxidant and antimicrobial activity determination of novel rel-(\(5R,6S,7R\))-6-benzoyl-7-phenyl-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-5-carboxylic acids. The target compounds were obtained in good yields from 5-arylidene-4-thioxo-2-thiazolidinones and \(\upbeta \)-aroylacrylic acids via regio- and diastereoselective hetero-Diels–Alder

  抽象的这里描述了新型rel-（\（5R，6S，7R \））-6-苯甲酰基-7-苯基-2-氧代-3,5,6,7-四氢-的合成，抗氧化剂和抗菌活性的测定2 H-硫代吡喃并[2，3 - d ]噻唑-5-羧酸。通过区域-和非对映选择性的杂-Diels-Alder反应，从5-芳叉基-4-硫代-2--2-噻唑烷酮和\（upbeta \）-芳酰基丙烯酸以高收率获得了目标化合物。通过NMR光谱证实了环加成的立体化学。进行抗氧化和抗菌活性筛选，鉴定出7种化合物（3c，3e，3f，3g，3k，3l，3p）具有高水平的自由基清除能力（43-77％DPPH测定），以及对金黄色葡萄球菌，枯草芽孢杆菌和白色念珠菌有显着影响的化合物（MIC 3.13-6.25 \（\ upmu \ hbox g / mL} \）），但对大肠杆菌有轻微影响。 图形概要
• Brandao; Rocha Filho; Chantegrel, Annales Pharmaceutiques Francaises, 1997, vol. 55, # 5, p. 206 - 211
  作者：Brandao、Rocha Filho、Chantegrel、Albuquerque、Ximenes、Galdino、Pitta、Perrissin、Luu-Duc

  DOI：——

  日期：——
• Albuquerque; Galdino; Chantegrel, Annales Pharmaceutiques Francaises, 1997, vol. 55, # 5, p. 201 - 205
  作者：Albuquerque、Galdino、Chantegrel、Thomasson、Pitta、Luu-Duc

  DOI：——

  日期：——