Synthesis, characterization and in vitro antibacterial activity of novel phthalazine sulfonamide derivatives

被引：30

作者：

Abbasi, Marzieh ^{[1
,4
]}

Nazifi, Seyed Mohamad Reza ^{[2
]}

Nazifi, Zahra Sadat ^{[1
,3
]}

Massah, Ahmad Reza ^{[1
,3
]}

机构：

[1] Islamic Azad Univ, Dept Chem, Shahreza Branch, Shahreza 86145311, Isfahan, Iran

[2] Isfahan Univ Med Sci, Sch Pharm & Pharmaceut Sci, Dept Med Chem, Esfahan, Iran

[3] Islamic Azad Univ, Shahreza Branch, Razi Chem Res Ctr, Shahreza 86145311, Isfahan, Iran

[4] Islamic Azad Univ, Shahreza Branch, Young Researchers & Elite Club, Shahreza, Isfahan, Iran

来源：

JOURNAL OF CHEMICAL SCIENCES | 2017年 / 129卷 / 08期

关键词：

Phthalazinesulfonamide; aldehyde; dimedone; sulfonated diatomite; heterogeneous catalyst; CATALYZED 3-COMPONENT SYNTHESIS; SOLVENT-FREE CONDITIONS; SILICA SULFURIC-ACID; ONE-POT SYNTHESIS; EFFICIENT CATALYST; PHARMACOLOGICAL EVALUATION; 4-COMPONENT SYNTHESIS; IONIC LIQUID; DESIGN; AGENTS;

D O I：

10.1007/s12039-017-1337-8

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Several phthalazine derivatives were synthesized by the one-pot three-component condensation in good to high yields in the presence of diatomite-SO3H as a solid acid catalyst. Then, a series (n= 14) of phthalazine sulfonamides were synthesized by the reaction phthalazine sulfonyl chloride and various amines under solvent-free conditions. The prepared compounds were screened for antibacterial activity against Escherichia coli (E. coli ATCC 25922) and Staphylococcus aureus (S. aureus ATCC 5213) as gram negative and positive respectively. Also, in silico physicochemical parameters of synthesized compounds were studied to predict absorption and permeability using Molinspiration online property calculation server.

引用

页码：1257 / 1266

页数：10

共 36 条

[1]

Al'-Assar F., 2002, PHARM CHEM J+, V36, P598, DOI [DOI 10.1023/A:1022665331722, 10.1023/a:1022665331722]

[2] Synthesis, biological, anti-inflammatory activities and quantum chemical calculation of some [4-(2, 4, 6-trimethylphenyl)-1(2H)-oxo-phthalazin-2yl] acetic acid hydrazide derivatives [J].

El-Shamy, Ibrahim E. ;

Abdel-Mohsen, A. M. ;

Alsheikh, Amer A. ;

Fouda, Moustafa M. G. ;

Al-Deyab, Salem S. ;

El-Hashash, Maher A. ;

Jancar, J. .

DYES AND PIGMENTS, 2015, 113 :357-371

[3] Design, synthesis and in vitro antitumor activity of novel N-substituted-4-phenyl/benzylphthalazin-1-ones [J].

Eldehna, Wagdy M. ;

Ibrahim, Hany S. ;

Abdel-Aziz, Hatem A. ;

Farrag, Noha N. ;

Youssef, Mohieldin M. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 89 :549-560

[4] Structural optimization of cyclic sulfonamide based novel HIV-1 protease inhibitors to picomolar affinities guided by X-ray crystallographic analysis [J].

Ganguly, Ashit K. ;

Alluri, Sesha S. ;

Wang, Chih-Hung ;

Antropow, Alyssa ;

White, Alex ;

Caroccia, Danielle ;

Biswas, Dipshikha ;

Kang, Eunhee ;

Zhang, Li-Kang ;

Carroll, Steven S. ;

Burlein, Christine ;

Fay, John ;

Orth, Peter ;

Strickland, Corey .

TETRAHEDRON, 2014, 70 (18) :2894-2904

[5] One-pot synthesis of aliphatic and aromatic 2H-indazolo[2,1-b]phthalazine-triones catalyzed by N-halosulfonamides under solvent-free conditions [J].

Ghorbani-Vaghei, Ramin ;

Karimi-Nami, Rahman ;

Toghraei-Semiromi, Zahra ;

Amiri, Mostafa ;

Ghavidel, Mehdi .

TETRAHEDRON, 2011, 67 (10) :1930-1937

[6] Solvent-free, one-pot, four-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones using sulfuric acid-modified PEG-6000 as a green recyclable and biodegradable polymeric catalyst [J].

Hasaninejed, Alireza ;

Kazerooni, Maryam Rasekhi ;

Zare, Abdolkarim .

CATALYSIS TODAY, 2012, 196 (01) :148-155

[7] Improvement of antibacterial activity of some sulfa drugs through linkage to certain phthalazin-1(2H)-one scaffolds [J].

Ibrahim, Hany S. ;

Eldehna, Wagdy M. ;

Abdel-Aziz, Hatem A. ;

Elaasser, Mahmoud M. ;

Abdel-Aziz, Marwa M. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 85 :480-486

[8] Structural variations in keto-glutamines for improved inhibition against hepatitis A virus 3C proteinase [J].

Jain, RP ;

Vederas, JC .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (14) :3655-3658

[9] Efficient one-pot syntheses of 2H-indazolo[2,1-b] phthalazine-triones by catalytic H2SO4 in water-ethanol or ionic liquid [J].

Khurana, Jitender M. ;

Magoo, Devanshi .

TETRAHEDRON LETTERS, 2009, 50 (52) :7300-7303

[10] Experimental and theoretical study on one-pot, three-component route to 2H-indazolo[2,1-b]phthalazine-triones catalyzed by nano-alumina sulforic acid [J].

Kiasat, Ali Reza ;

Noorizadeh, Siamak ;

Ghahremani, Mahboubeh ;

Saghanejad, Seyed Jafar .

JOURNAL OF MOLECULAR STRUCTURE, 2013, 1036 :216-225

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