4-isothiocyanato-benzenesulfonic acid pyrimidin-2-ylamide | 64047-46-7

• 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-isothiocyanato-benzenesulfonic acid pyrimidin-2-ylamide
• 英文别名: 4-Isothiocyanato-benzolsulfonsaeure-pyrimidin-2-ylamid；4-isothiocyanato-N-pyrimidin-2-ylbenzenesulfonamide
• CAS: 64047-46-7
• 化学式: C₁₁H₈N₄O₂S₂
• mdl: MFCD01716879
• 分子量: 292.342
• InChiKey: HZRFQEQYOQGXDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  4-isothiocyanato-benzenesulfonic acid pyrimidin-2-ylamide 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 56.0h， 生成
  参考文献：
  名称：

  N-[4-(N-取代氨磺酰基)苯基]氰基硫代甲酰胺在杂环化合物合成中的应用

  摘要：

  新型氰基硫代甲酰胺 2a-d 是通过在室温下用氰化钾处理异硫氰酸基磺酰胺 1a-d 制备的。化合物 2b,c 与异氰酸苯酯作为亲电试剂的环缩合反应得到相应的咪唑烷 3a,b。研究了化合物 3a 对一些氮亲核试剂的反应性。因此，氨基硫脲4和咪唑并[4,5-b]喹喔啉6分别通过化合物3a与氨基氨基硫脲和邻苯二胺的缩合合成。用盐酸处理 3a 得到化合物 7。我们的研究扩展到包括氰基硫代甲酰胺 2 对邻氨基苯酚、邻氨基苯甲酸和邻苯二胺的反应性，并分别产生相应的杂环 9、11 和 13 衍生物。

  DOI：

  10.1002/jccs.200400051
• 作为产物：
  描述：

  硫光气 、 磺胺嘧啶 在 盐酸 作用下， 以 水 为溶剂， 生成 4-isothiocyanato-benzenesulfonic acid pyrimidin-2-ylamide
  参考文献：
  名称：

  Synthesis, characterization and in vitro antimicrobial activity of novel 2-thioxo-4-thiazolidinones and 4,4′-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfones

  摘要：

  2-Thioxo-4-thiazolidinones (3a,b) were achieved by cyclocondensation of isothiocyanatosulfonamides (1a,b) with sulfanylacetic acid at reflux temperature in dioxane in the presence of triethylamine. Compound (3a) was exploited to synthesize the versatile hitherto unknown 2-thioxo-4-thiazolidinones (5-10) via its reaction with some electrophiles. Cyclization of 4,4'-diisothiocyanate diphenylsulfone (11) with sulfanylacetic acid furnished 4,4'-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfone (12) which on treatment with excess 4-methoxybenzaldehyde in refluxing dioxane in the presence of piperidine yielded the bisbenzylidene derivative (13). The novel synthesized compounds were characterized by IR, H-1 NMR and mass spectral studies. All the synthesized compounds were screened in vitro for their antibacterial and antifungal activities. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.05.005

文献信息

• SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF SOME NOVEL THIOUREA, NAPHTHO[2,3-d]THIAZOLE, QUINAZOLINE AND THIENO[2,3-d]PYRIMIDINE DERIVATIVES CONTAINING SULFONAMIDO MOIETIES
  作者：M. S. A. El-Gaby

  DOI：10.1080/10426500008045000

  日期：2000.1

  the corresponding acid hydrazide 6. Finally, treatment of 1a,b,d with 2-amind-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene yielded thieno[2,3-d]pyrimidines 10a-c bearing sulphonamido moieties. Structures of the new compounds were established by their elemental analyses and spectral data. Also, the most of these compounds were tested in vitro for their antimicrobial activity against some Gram positive and

  摘要 对取代的氨磺酰基苯基异硫氰酸酯 1a-d 是使用报道的程序制备的。研究了 1a-d 对一些含氮亲核试剂的反应性。因此，1 与芳香胺和邻氨基苯甲酸的相互作用提供了 N1,N3-二取代硫脲 2a-c 和 3-[4-N-取代磺酰氨基]苯基-2-thioxo-4-(3H)-quinazolin-4-ones 4a -f，分别。在含有无水碳酸钾的丙酮中用氯乙酸乙酯将 4c 烷基化得到喹唑啉 5。使用乙醇水合肼对 5 进行肼解得到相应的酰肼 6。最后，用 2-氨基-3-氰基-4 处理 1a、b、d ,5,6,7-四氢苯并[b]噻吩生成含有磺酰氨基部分的噻吩并[2,3-d]嘧啶10a-c。新化合物的结构是通过元素分析和光谱数据确定的。还，
• Design, synthesis and anticancer evaluation of novel tetrahydroquinoline derivatives containing sulfonamide moiety
  作者：Mostafa M. Ghorab、Fatma A. Ragab、Mostafa M. Hamed

  DOI：10.1016/j.ejmech.2009.05.017

  日期：2009.10

  many types of biological activities and have recently been reported to show substantial antitumor activity in vitro and/or in vivo. There are a variety of mechanisms for the anticancer activity and the most prominent of these is through the inhibition of carbonic anhydrase isozymes. The present work reports the synthesis of some novel quinoline and pyrimido[4,5-b]quinoline derivatives bearing a substituted

  磺酰胺具有许多类型的生物学活性，最近已报道其在体外和/或体内显示出显着的抗肿瘤活性。抗癌活性有多种机制，其中最主要的是通过抑制碳酸酐酶同工酶。本工作报告了一些新型喹啉和嘧啶基的合成[4,5- b带有取代或未取代的磺酰胺部分的对喹啉衍生物。这些化合物的结构设计符合充当碳酸酐酶（CA）抑制剂的磺酰胺化合物的一般药效基团，因为这可能在其抗癌活性中起作用。评价所有新合成的化合物对乳腺癌细胞系（MCF7）的体外抗癌活性。与参考药物相比，大多数被筛选的化合物显示出令人感兴趣的细胞毒性活性。
• The synthesis and transformations of some 3-thiocarbamoylthiazolidines
  作者：Mateja Malešič、Ales Krbavčíč、Amalija Golobič、Ljubo Golič、Branko Stanovnik

  DOI：10.1002/jhet.5570340108

  日期：1997.1

  In connection with our studies on potential bioactive compounds some new polysubstituted 3-thiocarbamoylthiazolidines 5, 6, 7, 9 and 10 were prepared in the reaction between 2-(2-methoxy-phenyl)iminothiazolidine (2) and sulfamoylphenyl isothiocyanates 3 and 4a-c. The structures for compounds 2 and 5 were established by X-ray analyses, showing that the reaction is taking place at the endo-cyclic nitrogen

  与我们对潜在生物活性的研究连接的化合物的一些新取代3- thiocarbamoylthiazolidines 5，6，7，9和10之间的2-（2-甲氧基-苯基）iminothiazolidine（2）和氨磺酰基苯基异硫氰酸酯反应制备3和4A- C。通过X射线分析建立了化合物2和5的结构，表明该反应在噻唑烷环的环内氮原子上发生。
• 2‐Thioxo‐3,4‐dihydropyrimidine and thiourea endowed with sulfonamide moieties as dual EGFRT790M and VEGFR‐2 inhibitors: Design, synthesis, docking, and anticancer evaluations
  作者：Mohamed S. A. El‐Gaby、Mohamed A. M. Abdel Reheim、Zuhir S. M. Akrim、Bassem H. Naguib、Nashwa M. Saleh、Abu Bakr A. A. M. El‐Adasy、Khaled El‐Adl、Samy Mohamady

  DOI：10.1002/ddr.22143

  日期：2024.2

  assessed for dual VEGFR-2 and EGFRT790M inhibition effects. Compounds 8f and 8g were the most potent derivatives inhibited VEGFR-2 at IC50 value of 0.88 and 0.90 µM, correspondingly. As well, derivatives 8f and 8g could inhibit EGFRT790M demonstrating strongest effects with IC50 = 0.32 and 0.33 µM sequentially. Additionally, the greatest active derivatives ADMET profile was evaluated in relationship

  在 HCT-116、MCF-7、HepG2 和 A549 上测试了一系列新的含有磺酰胺部分的硫代嘧啶和硫脲的有效性。 HepG2 细胞系是所有新衍生物中受影响最大的细胞系。针对四种 HepG2、HCT116、MCF-7 和 A549 细胞系最有效的化合物为8f和8g ，IC 50分别为 4.13、6.64、5.74、6.85 µM 和 4.09、4.36、4.22、7.25 µM。化合物8g对HCT116和MCF-7表现出比索拉非尼更高的活性，但对HepG2和A549表现出较低的活性。此外，化合物8f和8g对HepG2、HCT116和MCF-7表现出比厄洛替尼更高的活性，但对A549表现出较低的活性。在正常 VERO 细胞系上检查了最有效的细胞毒性衍生物6f 、 6g 、 8c 、 8d 、 8e 、 8f和8g 。我们的衍生物对 VERO 细胞具有低毒性，IC 50值范围为 32.05 至
• Synthesis and anti-Candidal activity of N-(4-aryl/cyclohexyl)-2-(pyridine-4-yl carbonyl) hydrazinecarbothioamide
  作者：Mashooq Ahmad Bhat、Abdul Arif Khan、Shahanavaj Khan、Mohamed A. Al-Omar、Mohammad Khalid Parvez、Mohammed Salem Al-Dosari、Abdullah Al-Dhfyan

  DOI：10.1016/j.bmcl.2014.01.060

  日期：2014.3

  Eighteen N-(4-aryl/cyclohexyl)-2-(pyridine-4-yl carbonyl) hydrazinecarbothioamide derivatives were synthesized, evaluated against ten clinical isolates of Candida spp. and compared with itraconazole. Introduction of p-chloro (2c), p-iodo (2q), m-chloro (2l) and o-nitro (2r) substitution at phenyl ring of thiosemicarbazide enhanced the anti-Candida activity. Compound (2c) bearing p-cholorophenyl ring was found to be the most effective against Candida albicans ATCC 66027, Candida spp. 12810 (blood) and Candida spp. 178 (HVS) with MIC value of 0.09-0.78 mu g/mL, whereas itraconazole exhibits the inhibitory activity with MIC value of 0.04-1.56 mu g/mL against all tested strains. There is a correlation between anti-Candidal activity and p-chloro substitution at phenyl ring of thiosemicarbazide. All synthesized compounds were investigated for their potential cytotoxicity against non cancer cell line MCF-10A. The active compounds 2c, 2r and 2a were further investigated for their cytotoxic effects on three cancer cell lines; HT1080 (skin), HepG2 (liver) and A549 (lung). The active compounds showed minimal cytotoxic activity against non cancer cell line and all three cancer cell lines. Moreover, compound 2c displaying better activity against C. albicans ATCC66027 and Candida spp. [blood] compared to reference drug (itraconazole), represents a good lead for the development of newer, potent and broad spectrum anti-Candidal agents. (C) 2014 Elsevier Ltd. All rights reserved.