First example of Azo-Sulfa conjugated chromene moieties: Synthesis,characterization, antimicrobial assessment,docking simulation as potent class I histone deacetylase inhibitors and antitumor agents |
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| Affiliation: | 1. Chemistry Department, Faculty of Science, Taibah University, 30002, Al-Madinah Al-Munawarah, Saudi Arabia;2. Pharmacognosy and Pharmaceutical Chemistry Department, Pharmacy College, Taibah University, Al-Madinah Al-Munawarah, Saudi Arabia;3. Clinical and Hospital Pharmacy Department, Taibah University, College of Pharmacy, Taibah University, Al-Madinah Al-Munawarah 41477, Saudi Arabia;4. Department of Chemistry, Faculty of Science, Al‐Azhar University at Assiut, Assiut 71524, Egypt;5. Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Al-Azhar University, 11884 Nasr City, Cairo, Egypt;6. Chemistry Department, Faculty of Science, Al-Azhar University, 11884 Nasr City, Cairo, Egypt;1. Pharmacognosy and Pharmaceutical Chemistry Department, College of Pharmacy, Taibah University, Al-Madinah Al-Munawarah, Saudi Arabia;2. Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt;3. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt;4. Pharmaceutical Chemistry Department, Faculty of Pharmacy, King Abdul-Aziz University, Jeddah, Saudi Arabia;5. Pharmacology and Toxicology Department, College of Pharmacy, Taibah University, Al-Madinah Al-Munawarah, Saudi Arabia;6. Department of Pharmacology and Toxicology, Faculty of Pharmacy, Beni-Suef University, Egypt;7. Department of Pharmaceutical and Medicinal Chemistry, Pharmacy College, Misr University for Science and Technology, Cairo, Egypt;8. Medicinal Chemistry Department, Faculty of Pharmacy, Assiut University, Assiut, Egypt;9. The Regional Center for Mycology and Biotechnology, Al-Azhar University, Cairo, Egypt;1. Chemistry Department, Faculty of Science, King Khalid University, Abha 61413, Saudi Arabia;2. Chemistry Department, Faculty of Science, Al-Azhar University, Cairo 11884, Egypt;3. Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, Egypt;4. Chemistry Department, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia;1. Faculty of Pharmacy, International Campus (TUMS-IC), Tehran University of Medical Sciences, Tehran, Iran;2. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran;3. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran;4. Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran;5. Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran;6. Department of Cellular Biotechnology at Cell Science Research Center, Royan Institute for Biotechnology, ACECR, Isfahan, Iran;7. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran;8. Department of Pharmacology, School of Medicine TUMS-IC, Tehran, Iran;9. Department of Medicinal Chemistry, Faculty of Pharmacy and Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran;1. Chemistry Department, Faculty of Science, King Khalid University, Abha 61413, Saudi Arabia;2. Chemistry Department, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia;3. Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City 11884, Cairo, Egypt;1. Department of Medicinal Chemistry, Shahreza Branch, Islamic Azad University, P.O. Box 311-86145, Shahreza, Isfahan, Iran;2. Faculty of Mechanical Engineering and Design, Kaunas University of Technology, Studentu Street 56, Kaunas, LT 51373, Lithuania;3. Department of Chemistry, Shahreza Branch, Islamic Azad University, P.O. Box 311-86145, Shahreza, Isfahan, Iran;4. Razi Chemistry Research Center (RCRC), Shahreza Branch, Islamic Azad University, Isfahan, Iran;5. Department of Organic Colorants, Institute for Color Science and Technology, P.O. Box 16656118481, Tehran, Iran;6. Advanced Materials Research Center, Department of Materials Engineering, Najafabad Branch, Islamic Azad University of Najafabad, P.O. Box 85141-43131, Najafbad, Isfahan, Iran;1. Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, 63100, Pakistan;2. Rural Health Centre Dera Bakha, Bahwalpur, Pakistan;3. Nishtar Medical University, Multan, Pakistan;4. Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan |
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| Abstract: | This report presents the development of a novel and primary model of sulfonamide compounds encompassing a chromene azo motif with the intent of becoming applicable for drug candidates in the cases of drug-resistant pathogens. The novel molecules (7a–n) have been synthesized via a two-step reaction. First, 4-((2, 4-dihydroxyphenyl)diazenyl)benzenesulfonamide (3a–e) were obtained through the reaction of their corresponding diazotized 4-aminobenzenesulfonamides (1a–e) with resorcinol, followed by the heterocyclization of 3a–e with arylidenemalononitriles (6a–d). Upon structural identification, the newly synthesized compounds were evaluated for their antibacterial and antifungal activities. Moreover, their cytotoxic screening was performed against three cancer cell lines: HCT-116, HepG-2, and MCF-7. Further examinations were comprised of the inhibitory effect analyses of the novel sulfonamide/chromene derivatives against the HDAC classes and the Tubulin polymerization in order to discern the prime antitumor drug candidates. |
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| Keywords: | Chromene Sulfonamide Antimicrobial Anticancer activity HDAC examination |
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