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Synthesis and Biological Evaluation of Sulfamoyl Carboxamide Derivatives from Sulfur-containing α-Amino acids


Paper Type 
Contributed Paper
Title 
Synthesis and Biological Evaluation of Sulfamoyl Carboxamide Derivatives from Sulfur-containing α-Amino acids
Author 
Melford C. Egbujor, Uchechukwu C. Okoro, Attah S. Egu, Vivian I. Okonkwo, Sunday N. Okafor, Chigbundu N. Emeruwa, Pius I. Egwuatu, Odera R. Umeh, Mercy I. Eziafakaego, Ifeanyi S. Amasiatu and David C. Nwobodo
Email 
nwobododave@gmail.com, egbujormc@gmail.com
Abstract:

    A series of new sulfamoyl carboxamide analogs were synthesized using sulfur-containing amino acids and sulfonyl chloride. The characterization of the compounds was done using FTIR, 1H-NMR, 13C-NMR, and elemental analysis. Their antioxidant, antimalarial, antimicrobial activities and molecular docking were evaluated. Compounds 5h (MIC, 0.3, 0.5, 0.3 and 0.4 mg/mL) was the most potent antibacterial agent against Staphylococcus aureus, Escherichia coli, Bacillus subtilis and Salmonella typhi, compounds 5a (MIC, 0.7 mg/mL) and 5g (MIC, 0.7m g/mL) were most potent against Pseudomonas aeruginosa while compound 5e (MIC, 0.5 and 0.8 mg/mL) had the best in vitro antifungal activity against Aspergillus niger and Candida albicans. Compound 5d (1C50 = 1.128 μg/mL) displayed an antioxidant activity comparable with ascorbic acid (1C50 = 1.000 μg/mL) and compound 5e (4, 14, 4%) effected the most significant reduction in the percentage malaria parasitaemia comparable with artemeter lumefantrin (5, 4, 4%) after 5 days of treatment of the mice. From the molecular docking results, compound 5c had a strong molecular interaction with the appropriate drug target, Escherichia coli DNA gyrase complexed with 1-ethyl-3-[8-methyl-5-(2-methyl-pyridin-4-yl) isoquinolin-3-yl]urea (PDB code: 5MMN). The title compounds displayed signifi cant antimicrobial, antioxidant and antimalarial activities.

Start & End Page 
1100 - 1115
Received Date 
2022-03-08
Revised Date 
2022-05-21
Accepted Date 
2022-05-25
Full Text 
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Keyword 
antimalarial, antimicrobial, antioxidant, carboxamide, sulphonamide, methionine, cysteine, molecular docking
Volume 
Vol.49 No.4 (July 2022)
DOI 
https://doi.org/10.12982/CMJS.2022.070
Citation 
Egbujor M.,C.,Okoro U.,C.,Egu A.,S.,Okonkwo V.,I.,Okafor S.,N.,Emeruwa C.,N., et al., Synthesis and Biological Evaluation of Sulfamoyl Carboxamide Derivatives from Sulfur-containing α-Amino acids, Chiang Mai Journal of Science, 2022; 49(4): 1100-1115. DOI 10.12982/CMJS.2022.070.
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page: 176 - 183
Author:Thidarat Somdee *, Udomsak Mahaweerawat, Jindawan Wibulutai, Namphuang Dungkokruad and Suneerat Yung
Vol.44 No.1 (JANUARY 2017) View: 838 Download:1,674
Ultrasonic Extraction, Antioxidant and Anti-glycation Activities of Polysaccharides from Gynura divaricata Leaves
page: 144 - 156
Author:Pawinee Deetae*[a, e], Kwanrudee Tseng [a], Chanathinart Pasuphan [a], Atikorn Panya [b], Pawadee Methacanon [c], Waranya Temthawee [a] and Manop Suphantharika [d]
Vol.44 No.1 (JANUARY 2017) View: 1,867 Download:343
Phenolic Profile, Fatty Acid and Essential Oil Composition Analysis and Antioxidant, Antialzheimer and Antibacterial Activities of Verbascum flavidum Extracts
page: 1090 - 1101
Author:Mehmet Boğa*[a], Abdulselam Ertaş [b], Nesrin Haşimi [c], Serpil Demirci [d], Mustafa Abdullah Yılmaz [e], Hamdi Temel [f] and Ufuk Kolak [g]
Vol.43 No.5 (OCTOBER 2016) View: 799 Download:231
Antioxidant Compounds and Activities in Selected Fresh and Blanched Vegetables from Northeastern Thailand
page: 834 - 844
Author:Thidarat Somdee*[a], Udomsak Mahaweerawat [a], Methin Phadungkit [b] and Suneerat Yangyuen [a]
Vol.43 No.4 (JULY 2016) View: 707 Download:234
Synthesis, Characterization and Antioxidant Activity of 2-Halobenzoyl Thiourea bearing α- and β-Alanine
page: 578 - 584
Author:Nurziana Ngah*, Nor Azanita Mohamed, and Deny Susanti Darnis
Vol.43 No.3 (APRIL 2016) View: 731 Download:245
Determination of Antioxidant and Anticancer Activities together with Total Phenol and Flavonoid Contents of Cleidion javanicum Bl. and Bridelia retusa (L.) A. Juss.
page: 535 - 546
Author:Duangsuree Sanseera, Boonsom Liawruangrath *, Stephen G. Pyne and Saisunee Liawruangrath*
Vol.43 No.3 (APRIL 2016) View: 1,232 Download:539
Phytochemical Constituents with Antimicrobial and Antioxidant Activities from Xylia xylocarpa (Roxb.) Taub. Sawdust Extracts
page: 11 - 21
Author:Pattarawadee Sumthong Nakmee* [a], Soontree Khuntong [a] and Nitra Nuengchamnong [b]
Vol.43 No.1 (JANUARY 2016) View: 789 Download:319
Optimization of the Preparation of Gelatin Hydrolysates with Antioxidative Activity from Lizardfish (Saurida spp.) Scales Gelatin
page: 68 - 79
Author:Sutee Wangtueai [a, b]*, Susanne Siebenhandl-Ehn [c] and Dietmar Haltrich [c]
Vol.43 No.1 (JANUARY 2016) View: 878 Download:467
Antioxidant Capacity and Phenolic Content Evaluation on Peanut Skins from 3 Peanut Types
page: 123 - 137
Author:Pornnapa Chuenchom, Prasan Swatsitang, Thanaset Senawong, Sanun Jogloy
Vol.43 No.1 (JANUARY 2016) View: 842 Download:498
Insights Into The Causes and Anti-hyperglycemic Effects Of Punica granatum Rind in Alloxan-induced Diabetic Rats
page: 112 - 122
Author:Sushil Kumar Middha [a,c], Talambedu Usha [b]* and Veena Pande [a]
Vol.43 No.1 (JANUARY 2016) View: 689 Download:210
Ameliorating Reactive Oxygen Species-Induced in vitro Lipid Peroxidation in Liver, Carbohydrate and DNA Damage by Dendrocalamus hamiltonii Different Leaf Extracts
page: 80 - 88
Author:Arvind Kumar Goyal [a,b], Sushil Kumar Middha [c], Talambedu Usha [c] and Arnab Sen*[a]
Vol.43 No.1 (JANUARY 2016) View: 747 Download:171
Fatty Acid, Essential Oil and Phenolic Compositions of Alcea pallida and Alcea apterocarpa with Antioxidant, Anticholinesterase and Antimicrobial Activities
page: 89 - 99
Author:Abdulselam Ertas*[a,b], Mehmet Boga [b,c], Isil Gazioglu [d], Yeter Yesil [e] , Nesrin Hasimi [f], Cumali Ozaslan [g], Hasibe Yilmaz[h], Muammer Kaplan[j]
Vol.43 No.1 (JANUARY 2016) View: 752 Download:297
Comparative Studies on Chemical Composition, Phenolic Compounds and Antioxidant Activities of Brown and White Perilla (Perilla frutescens) Seeds
page: 896 - 906
Author:Sikeret Kongkeaw, Siriporn Riebroy and Manat Chaijan
Vol.42 No.4 (OCTOBER 2015) View: 824 Download:254
HPTLC Analysis, Antioxidant, Anti-Inflammatory and Xanthine Oxidase Inhibitory Activity of Plumbago zeylanica L
page: 886 - 895
Author:Shivraj Hariram Nile, Umesh Bapurao Patil and Se Won Park
Vol.42 No.4 (OCTOBER 2015) View: 746 Download:378
Prediction of Antioxidant Capacity of Thai Vegetable Extracts by Infrared Spectroscopy
page: 657 - 668
Author:Trakul Prommajak, Sang Moo Kim, Cheol-Ho Pan, Sang Min Kim, Suthat Surawang, Nithiya
Vol.42 No.3 (JULY 2015) View: 764 Download:257
Determination of the Effects of Adding Milk and Sugar on the Antioxidant Capacity of Oolong Tea by Chemical and Cell Culture-Based Antioxidant Assays
page: 699 - 711
Author:Angkana Wipatanawin, Sudarat Phongsawanit, Thadthanan Maneeratprasert, Sittiwat Lertsiri
Vol.42 No.3 (JULY 2015) View: 825 Download:243
Fatty Acid Composition, Physical Properties, Acute Oral Toxicity and Antioxidant Activity of Crude Lipids from Adipose Tissue of Some Commercialized Freshwater Catfish
page: 626 - 636
Author:Wiwat Wangcharoen, Kriangsak Mengumphan and Doungporn Amornlerdpison
Vol.42 No.3 (JULY 2015) View: 722 Download:194
Synthesis, Characterization and Antimicrobial Evaluation of Transition Metal Complexes of Monodentate 2-(Substituted Phenyl)-1H-benzo[d]imidazoles
page: 216 - 227
Author:Minaxi S Maru and Manish K Shah
Vol.42 No.1 (JANUARY 2015) View: 799 Download:259
Phenolics production from a novel substrate palm oil mill effluent by Aspergillus niger IBS-103ZA: Evaluation of fermentation conditions and antioxidant activity
page: 1 - 16
Author:Zulkarnain Mohamed Idris, Parveen Jamal, Md Zahangir Alam, Abdul Haseeb Ansari, A
Vol.42 No.1 (JANUARY 2015) View: 759 Download:234
Plasma Assisted Immobilization of TiO2 nanoparticles onto PLA Surface to Promote the Antimicrobial Activity
page: 1361 - 1374
Author:Chonlada Theerakarunwong*[a], Somruthai Tunma[b] and Dheerawan Boonyawan[c]
Vol.41 No.5/2 (OCTOBER 2014) View: 657 Download:217
In vitro Antioxidant and Antitumor Activities of an Endophytic Fungus Phomopsis liquidambari QH4 from Artemisia annua
page: 992 - 1006
Author:Yixin Qian [a, b], Jichuan Kang*[a, c], Lu Wang [a], Bangxing Lei [a] and Kevin D. Hyde [d, e]
Vol.41 No.5/1 (OCTOBER 2014) View: 722 Download:244
Gastroprotective Effects and Antioxidant Activities of Paederia pilifera Hook.f. Root Extract
page: 1121 - 1131
Author:Kantarat Jirakittirat, Supap Saenphet and Kanokporn Saenphet*
Vol.41 No.5/1 (OCTOBER 2014) View: 697 Download:213
Phenolic acids content and antioxidant capacity of fruit extracts from Thailand
page: 636 - 642
Author:Nattaya Ongphimai [a], Supathra Lilitchan*[a], Kornkanok Aryusuk [b], Akkarach Bumrungpert [a], et a
Vol.40 No.4 (OCTOBER 2013) View: 805 Download:265
Physical Characteristics and Biological Activities of Thai Flower Extracts Loaded in Niosomes
page: 603 - 617
Author:Aranya Manosroi*[a,b], Bang-on Kietthanakorn [b], Charinya Chankhampan [b], Narinthorn Khositsuntiwo
Vol.40 No.4 (OCTOBER 2013) View: 768 Download:293
Role of Quercetin and L-Arginine in Alleviating Zinc Oxide Nanoparticle Hepatotoxicity in Rats
page: 577 - 592
Author:Nayira A. Abdel Baky [a]*, L.M. Faddah [a] , Nouf M. Al-Rasheed [a], Nawal M. Al-Rasheed [a] , and W
Vol.40 No.4 (OCTOBER 2013) View: 772 Download:254
The Potential of Electrospun Poly(L-lactic Acid) Fiber Mats Containing a Crude Garcinia Dulcis Extract for Use as Wound Dressings
page: 517 - 533
Author:Orawan Suwantong *[a], Porntipa Pankongadisak [a], Suwanna Deachathai [a] and Pitt Supaphol [b]
Vol.40 No.3 (JULY 2013) View: 709 Download:234
Development of Sequential Injection Analysis Using Peristaltic Pump and Electrochemical Detection for Antioxidant Capacity Test by ABTS Assay
page: 224 - 231
Author:Jakkrapun Kongkedsuk [a], Apisake Hongwitayakorn [a], Wannarekha Bootnapang [b], Nisachon Boonto [b
Vol.40 No.2 (APRIL 2013) View: 1,177 Download:270
Antimicrobial and Antioxidant Activities of Methanol, Dichloromethane and Ethyl Acetate Extracts of Scutellaria lindbergii Rech.f.
page: 49 - 59
Author:Bibi Sedigheh Fazly-Bazzaz *[a], Atefeh Arab [b], Seyed Ahmad Emami [c], Javad Asili [c], Mohamad Ha
Vol.40 No.1 (JANUARY 2013) View: 760 Download:271
Antioxidant Potential of Pleurotus porrigens Extract and Application in Sunflower Oil during Accelerated Storage
page: 34 - 48
Author:Hip Seng Yim*[a, b], Fook Yee Chye [b], Mei Lian Liow [a], and Chun Wai Ho [a]
Vol.40 No.1 (JANUARY 2013) View: 775 Download:276
Screening of Volcanic Cave Actinomycetes for Antimicrobial Activity Against Paenibacillus larvae, A Honey Bee Pathogen
page: 26 - 33
Author:Silvia Kay [a], Wasu Pathom-aree [b], and Naowarat Cheeptham*[a]
Vol.40 No.1 (JANUARY 2013) View: 773 Download:312
Preparation, characterization, and antimicrobial activity of electrospun nanofibers from cotton waste fibers
page: 712 - 722
Author:Piyaporn Kampeerapappun*
Vol.39 No.4 (OCTOBER 2012) View: 698 Download:211
Antioxidant and Sensory Properties of Thai Herbal Teas with emphasis on Thunbergia laurifolia Lindl.
page: 599 - 609
Author:Eric W.C. Chan*, Suit Ying Eng, Yuen Ping Tan, Zhiew Cheng Wong, Phui Yan Lye, and Lea Ngar Tan
Vol.39 No.4 (OCTOBER 2012) View: 814 Download:266
Nutritional and Physicochemical Qualities of Thua Nao (Thai Traditional Fermented Soybean)
page: 562 - 574
Author:Katekan Dajanta1,2, Ekachai Chukeatirote3,* and Arunee Apichartsrangkoon2
Vol.39 No.4 (OCTOBER 2012) View: 716 Download:275
Evaluation of Effective Entomopathogenic Fungi to Fruit Fly Pupa, Bactrocera spp., and Their Antimicrobial Activity
page: 464 - 477
Author:Thet Thet Mar and Saisamorn Lumyong*
Vol.39 No.3 (JULY 2012) View: 685 Download:265
Antioxidant, Antibacterial, Anticancer Activities and Chemical Constituents of the Essential Oil from Mesua ferrea Leaves
page: 455 - 463
Author:Sukanya Keawsa-ard* [a] and Samart Kongtaweelert [b]
Vol.39 No.3 (JULY 2012) View: 785 Download:562
In vitro INHIBITION OF LIPID PEROXIDATION AND THE ANTIOXIDANT SYSTEM OF ENDOPHYTIC FUNGI FROM THAI MEDICINAL PLANTS
page: 429 - 444
Author:Teerayut Theantana [a,b], Duangta Kanjanapothi [c], Saisamorn Lumyong* [b]
Vol.39 No.3 (JULY 2012) View: 753 Download:209
Comparative Analysis of Aqueous Extracts of Amaranth and Coriander in Scavenging Free Radical Activity and Protection of DNA against Oxidative Damage
page: 560 - 571
Author:Asmita Dutta and Mukesh Singh
Vol.38 No.4 (OCTOBER 2011) View: 720 Download:315
Antibacterial Activity of Bauhinia acuminata L. Seed Protein Extract with Low Hemolytic Activity Against Human Erythrocytes
page: 242 - 251
Author:Karaket Phansri [a], Rakrudee Sarnthima [a], Sompong Thammasirirak [b], Pasakorn Boonchalee [c] and
Vol.38 No.2 (APRIL 2011) View: 808 Download:243
Antitubercular and Antiplasmodial Prenylated Flavones from the Roots of Artocarpus altilis
page: 339 - 344
Author:Surat Boonphong , Apiwat Baramee, Prasat Kittakoop , and Pakawan Puangsombat
Vol.34 No.3 (SEPTEMBER 2007) View: 780 Download:291
Antioxidant Capacity of Broccoli Seeds Grown in Thailand
page: 117 - 122
Author:Sarunya Chuanphongpanich* [a], Maitree Suttajit [b], Sukon Phanichphant [c Duang Buddhasukh [c]
Vol.33 No.1 (JANUARY 2006) View: 732 Download:222
Extraction of Phenolic Compounds from Fruits of Bitter Melon (Momordica charantia ) with Subcritical Water Extraction and Antioxidant Activities of These Extracts
page: 123 - 130
Author:Parichat Budrat and Artiwan Shotipruk
Vol.35 No.1 (JANUARY 2008) View: 732 Download:527
Red Yeast Rice Prepared from Thai Glutinous Rice and the Antioxidant Activities
page: 42 - 49
Author:Em-on Chairote, Griangsak Chairote, and Saisamorn Lumyong
Vol.36 No.1 (JANUARY 2009) View: 798 Download:278
Screening of Antioxidants from Some Thai Vegetables and Herbs
page: 1 - 5
Author:Anchana Chanwitheesuk, Nuansri Rakariyatham*, Aphiwat Teerawutgulrag and Teerapol Wongchanapiboon
Vol.29 No.1 (APRIL 2002) View: 848 Download:271
Inhibitory Effect of Thermotolerant Lactic Acid Bacteria on the Growth of Bacillus cereus, Staphylococcus aureus, Salmonella enteritidis and Vibrio parahaemolyticus
page: 119 - 124
Author:Atchara Lapmak [a], Sumana Kumpai [b] and Abhinya Plikomol*[b]
Vol.28 No.2 (DECEMBER 2001) View: 816 Download:228
Antimalarial Activity in Vitro of Some Natural Extracts from Vitex trifolia
page: 9 - 13
Author:Sombat Chowwanapoonpohn and Apiwat Baramee
Vol.27 No.1 (JUNE 2000) View: 823 Download:252
Antioxidant and Anti-inflammatory Activities of Brown Marine Alga, Padina minor Yamada
page: 507 - 516
Author:Yuwadee Peerapornpisal, Doungporn Amornlerdpison, Utan Jamjai, Tawat Taesotikul, Yanee Pongpaibul,
Vol.37 No.3 (SEPTEMBER 2010) View: 757 Download:299
In vitro Antioxidant Activity of Vitex negundo L. Leaf Extracts
page: 489 - 497
Author:Raghavendra H. Lakshmanashetty, Vijayananda B. Nagaraj, Madhumathi G. Hiremath and Vadlapudi Kumar
Vol.37 No.3 (SEPTEMBER 2010) View: 1,285 Download:1,049



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