Synthesis of Novel 3-Substituted Pyridothienopyrimidine Derivatives with Biological Evaluation as Antimicrobial Agents

doi:10.1007/s40242-016-6218-z

高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (6): 967-972.doi: 10.1007/s40242-016-6218-z

Synthesis of Novel 3-Substituted Pyridothienopyrimidine Derivatives with Biological Evaluation as Antimicrobial Agents

Farag A. El-Essawy^1,2, Nader M. Boshta², Ayman K. El-Sawaf^3,2, Amal A. Nassar⁴, Mohamed S. Khalafallah²

1. Preparatory Year Deanship, Basic Science Department, Prince Sattam Bin Abdulaziz University, KSA;
2. Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koam, Egypt;
3. Collage of Science and Humanities, Prince Sattam Bin Abdulaziz University, KSA;
4. Faculty of Education for Girls, Prince Sattam Bin Abdulaziz University, KSA

收稿日期:2016-05-26 修回日期:2016-08-19 出版日期:2016-12-01 发布日期:2016-08-30
通讯作者: Farag A. El-Essawy, E-mail:faragelessawy@gmail.com E-mail:faragelessawy@gmail.com
基金资助:
Supported by the Deanship of Scientific Research at Prince Sattam Bin Abdulaziz University(No.2015/01/4713).

Synthesis of Novel 3-Substituted Pyridothienopyrimidine Derivatives with Biological Evaluation as Antimicrobial Agents

Farag A. El-Essawy^1,2, Nader M. Boshta², Ayman K. El-Sawaf^3,2, Amal A. Nassar⁴, Mohamed S. Khalafallah²

1. Preparatory Year Deanship, Basic Science Department, Prince Sattam Bin Abdulaziz University, KSA;
2. Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koam, Egypt;
3. Collage of Science and Humanities, Prince Sattam Bin Abdulaziz University, KSA;
4. Faculty of Education for Girls, Prince Sattam Bin Abdulaziz University, KSA

Received:2016-05-26 Revised:2016-08-19 Online:2016-12-01 Published:2016-08-30
Contact: Farag A. El-Essawy, E-mail:faragelessawy@gmail.com E-mail:faragelessawy@gmail.com
Supported by:
Supported by the Deanship of Scientific Research at Prince Sattam Bin Abdulaziz University(No.2015/01/4713).

摘要/Abstract

摘要：

Novel 3-substituted pyridothienopyrimidine derivatives have been synthesized via the reaction of 2-{7,9-dimethyl-4-oxopyrido[3',2':4,5]thieno[3,2-d]pyrimidin-3(4H)-yl}acetohydrazide(5) with a variety of active reagents and chemicals. Structures of the newly synthesized compounds were established based on spectral data. The resulting pyridothienopyrimidine derivatives were evaluated for their possible antimicrobial activity and some of them represent a new class of potentially antimicrobial compounds, especially compounds 9 and 18 which displayed the highest activity against Gram-positive bacteria, Gram-negative bacteria, and Fungi in MIC range of 0.12-1.95 μg/mL.

关键词: Nitrogen-containing heterocycle, Pyridothienopyrimidine, Thieno[2,3-b]pyridine, Antimicrobial

Abstract:

Key words: Nitrogen-containing heterocycle, Pyridothienopyrimidine, Thieno[2,3-b]pyridine, Antimicrobial

Farag A. El-Essawy, Nader M. Boshta, Ayman K. El-Sawaf, Amal A. Nassar, Mohamed S. Khalafallah. Synthesis of Novel 3-Substituted Pyridothienopyrimidine Derivatives with Biological Evaluation as Antimicrobial Agents[J]. 高等学校化学研究, 2016, 32(6): 967-972.

参考文献

[1] Vitaku E., Smith D. T., Njardarson J. T., J. Med. Chem., 2014, 57(24), 10257
[2] Khattab A. F., El-Sakka I. A., Yassin S. M., El-Essawy F. A. G., Sulfur. Lett., 1995, 19(1), 23
[3] Bousquet E., Romeo G., Guerrera F., Caruso A., Amico-Roxas M., Farmaco, 1985, 40(11), 869
[4] Badr M. Z. A., Mahgoub S. A., Abdel-Latif F. F., Abd El-Hafez A. A. A., Phosphorus, Sulfur SiliconRelat. Elem., 1991, 55(1-4), 175
[5] Bernardino A. M., da Silva PinheiroL. C., Rodrigues C. R., Loureiro N. I., Castro H. C., Lanfredi-Rangel A., Sabatini-Lopes J., Borges J. C., Carvalho J. M., Romeiro G. A., Ferreira V. F., Bioorg. Med. Chem., 2006, 14(16), 5765
[6] Al-Trawneh S. A., El-Abadelah M. M., Zahra J. A., Al-Taweel S. A., Zani F., Incerti M., CavazzoniA., Vicini, P., Bioorg. Med. Chem., 2011, 19(8), 2541
[7] Abdel-Rahman A. E., Bakhite E. A., Al-Taifi E. A., J. Chin. Chem. Soc., 2002, 49(2), 223
[8] Leistner S., Wagener G., Guestscharo M., Glusa E., Pharmazie, 1986, 41(1), 54
[9] Bousquent E., Romero G., Guerrera F., Caruso A., Roxas M. A., Farmaco Ed. Sci., 1985, 40, 869
[10] Zhao C., Tovar C., Yin X., Xu Q., Todorov I. T., Vassilev L. T., Chen L., Bioorg. Med. Chem. Lett., 2009, 19(2), 319
[11] Abdelriheem N. A., Ahmad S. A. K., Abdelhamid A. O., Molecules, 2015, 20(1), 822
[12] Bing S., Xiu'e Y., Jin Z., Jian H., Yue X., Furong Z., Jinhui W., Guoqing W., Chun H., Chem. Res. Chinese Universities, 2015, 31(6), 936
[13] Litvinov V. P., Dotsenko V. V., Krivokolysko S. G., NaukaMoscow, 2006, 72
[14] Hossan A. S. M., Abu-Melha H. M. A., Al-Omar M. A., Amr A. E. E., Molecules, 2012, 17(11), 13642
[15] Bakhite E. A., Abdel-Rahman A. E., Mohamed O. S., Thabet E. A., Bull. Korean Chem. Soc., 2002, 23(12), 1709
[16] Rateb N. M., Abdelaziz S. H., Zohdi H. F., J. Sulfur Chem., 2011, 32(4), 345
[17] Gaber H. M., Elgemeie G. E. H., Ouf S. A., Sherif S. M., Heteroatom Chem., 2005, 16(4), 298
[18] El-Essawy F. A., Nucleos. Nucleot. Nucl., 2005, 24(8), 1265
[19] El-Essawy F. A., Chem. Heterocycl. Comp., 2009, 45(7), 837
[20] El-Essawy F. A., Hawatta M. A., Abdel-Megied A. E., El-Sherbeny D. A., Chem. Heterocycl. Comp., 2010, 46(3), 325
[21] El-Essawy F. A., J. Heterocyclic. Chem., 2010, 47(2), 318
[22] El-Essawy F. A., Synthetic Commun., 2010, 40(6), 877
[23] Peinador C., Ojea V., Quintela J. M., J. Heterocycl. Chem., 1992, 29(7), 1693
[24] Quintela J. M., Peinador C., Veiga C., Gonzales L., Botana L. M., Alfonso A., Riguera R., Bioorg. Med. Chem., 1998, 6(10), 1911
[25] El-Essawy F. A., El-Sayed W. A., J. Heterocyclic. Chem., 2013, 50(S1), E1
[26] Clinical and Laboratory Standards Institute, Performance Standards for Antimicrobial Susceptibility Testing, Twenty-Fourth Informatio-nal Supplement(M100-S24), Wayne, 2014, 34(1), 1

Synthesis of Novel 3-Substituted Pyridothienopyrimidine Derivatives with Biological Evaluation as Antimicrobial Agents

Synthesis of Novel 3-Substituted Pyridothienopyrimidine Derivatives with Biological Evaluation as Antimicrobial Agents

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 6

编辑推荐

Metrics

本文评价

[1]	YAN Liuqing, FU Jiaxu, LI Shuang, ZHANG Jinlong, WANG Shuang, GU Qiang, ZHANG Yumin, LIN Feng. Microwave-assisted Catalyzed Synthesis and In vitro Bioactivity Evaluation of Benzimidazoles Bearing Phenolic Hydroxyl[J]. 高等学校化学研究, 2021, 37(3): 639-646.
[2]	FENG Fan, LI Jing, ZHANG Zhihui, FU Jiaxu, ZHANG Yumin, GU Qiang. Design, Ultrasonic-assisted Synthesis and Evaluation In vitro Antimicrobial Activity of Bis-isoxazole Derivatives Bearing Chloro-pyridinyl Group[J]. 高等学校化学研究, 2021, 37(3): 668-673.
[3]	YANG Jiajia, WANG Meng, LI Xia, FAN Ningning, XUE Liangmin, LI Hao, TIAN Chao, WANG Xiaowei, LIU Junyi, ZHANG Zhili. Syntheses and Antiproliferative Evaluation of 6-Thienyl, 6-Polyphenyl Aryl and 6-Naphthyl Derivatives of 2,4-Diaminopyrido[3,2-d]pyramidine as Non-classical Antifolate Targeting DHFR[J]. 高等学校化学研究, 2017, 33(4): 559-568.
[4]	XU Qing-hui, LI Ji-zhen, HE Jiang-hua, ZHAO Xin, HUO Qi-sheng. Synthesis of Novel Flavanone Derivatives and Their Anti Staphylococcus aureus Evaluation[J]. 高等学校化学研究, 2013, 29(4): 695-698.
[5]	HU Xi-yu, CHEN Bing-nian, WANG Li, CHEN Fa-he. Inhibition of α/β-K₆P₂W₁₈O₆₂·10H₂O on the Activity of Mushroom Tyrosinase and Its Antimicrobial Effects[J]. 高等学校化学研究, 2012, 28(5): 862-865 .
[6]	CHEN Feng-ying, WU Wang-ting, LI Heng-xin, HE Shui-yang, WEN Zhen-yi, LI Jia-xing. Molecular Structure and Properties of a Novel Acylhydrazone (C₁₄H₁₄O₆N₄)·HCON(CH₃)₂·2H₂O[J]. 高等学校化学研究, 2012, 28(3): 524-528.