تحضير وتشخيص مشتقات 2-امينو -5-كلوروبنزوثايزول جديدة تحوي على انواع مختلفة من حلقات غير المتجانسة كمضادات للفطريات
محتوى المقالة الرئيسي
الملخص
تم في هذا البحث تحضير تسع مركبات جديدة من مشتقات 2-امينو-5-كلورو بنزوثايزول من خلال تفاعل2-امينو -5-كلوروبنزوثايزول 1مع اثيل كلورواسيتيت بوجود KOH ليعطي مشتق2-امينو -5-كلوروبنزوثايزول استر2 ادخل الاخير بعدة مسارات ، تفاعل مشتق الاستر مع هيدرازين هيدريت لتعطي مشتق الهيدرازايد3 ومفاعلة المركب الاخير مع CS2 بوجود KOH ليعطي مشتق 1,3,4اكساديزول-2-ثايول (4) بعدها تم مفاعله مركب الاستر المحضر مع ثايو سيمكاربزايد ليعطي مركب 5 ثم الغلق الحلقي بواسطه4%من هيدروكسيد الصوديوم ليعطي مشتق 1,2,4-ثايزول -3-ثايول 6 في مسار اخر تم مفاعله 2-امينو-5-كلورو بنزوثايزول مع حامض كلورو اسيتك اسد ليعطي مركب 7 الذي تم مفاعلته مع ارثو امينو انلين ليعطي بنزيميدازول 8.تم الحصول على مشتق ازوميثين 9 من خلال تفاعل2-امينو6-كلوروبنزثايزول مع بروموبنزالديهايد. المركب الاخير 9حول الى مشتق ثايوزولدينون 10 من خلال تفاعله مع 2-مركبتواسيتك اسد. المركبات المحضرة تم تشخيصها من خلال استعمال طيف الأشعة تحت الحمراء وطيف بروتون النووي المغناطيسي وتحليل العناصر C.H.N وتعيين الصفات الفيزياوية لكل المركبات المحضرة. كما تم فحص الفعالية البايولوجيه للمركبات المحضرة تجاه نوعين من الفطريات وأظهرت النتائج لبعض فعاليات قياسية جيدة بالمقارنة مع العقار القياسي فلوكينازول.
Received 03/01/2023
Revised 17/03/2023
Accepted 19/03/2023
Published Online First 20/08/2023
تفاصيل المقالة
هذا العمل مرخص بموجب Creative Commons Attribution 4.0 International License.
كيفية الاقتباس
المراجع
Yang Hu, Cui-Yun Li, Xiao-Ming Wang, Yong-Hua Yang, Hai-Liang Zhu. 1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry. Chem Rev. 2014 ; 114 (10): 5572-5610. https://doi.org/10.1021/cr400131u.
Irfan A, Batool F, Zahra Naqvi SA, Islam A, Osman SM, Nocentini A, et al. Benzothiazole derivatives as anticancer agents. J Enzyme Inhib Med Chem. 2020 ; Dec; 35(1): 265-279. https://doi.org/10.1080/14756366.2019.1698036
Ismail MMF, Abdulwahab HG, Nossier ES, El Menofy NG, Abdelkhalek BA. Synthesis of novel 2-aminobenzothiazole derivatives as potential antimicrobial agents with dual DNA gyrase/topoisomerase IV inhibition. Bioorg Chem. 2020 May; 98: 103716. https://doi.org/10.1016/j.bioorg.2019.103437
Zhilitskaya LV, Yarosh NО. Synthesis of biologically active derivatives of 2-aminobenzothiazole. Chem Heterocycl Comp. 2021; 57: 369–373. https://doi.org/10.1007/s10593-021-02914-6
Nikhil D, Amnerkar Kishore P. Bhusari. Synthesis of some thiazolyl aminobenzothiazole derivatives as potential antibacterial, antifungal and anthelmintic agents. J Enzyme Inhib Med Chem. 2011; 26(1): 22-28. https://doi.org/10.3109/14756360903555258
Alminderej F, Lotfi A. Design, Synthesis, Characterization and Anticancer Evaluation of Novel Mixed Complexes Derived from 2-(1H-Benzimizadol-2-yl)aniline Schiff base and 2-Mercaptobenzimidazole or 2-Aminobenzothiazole. Egypt J Chem. 2021; 64(7): 3351-3364. https://doi.org/10.21608/ejchem.2021.60640.3305.
Montalvão S, Leino TO, Kiuru PS, Lillsunde KE, Yli-Kauhaluoma J, Tammela P. Synthesis and Biological Evaluation of 2-Aminobenzothiazole and Benzimidazole Analogs Based on the Clathrodin Structure. Arch Pharm (Weinheim). 2016; 349(2): 137-149. https://doi.org/10.1002/ardp.201500365
Haroun M, Petrou A, Tratrat C, Kositsi K, Gavalas A, Geronikaki A, et al. Discovery of benzothiazole-based thiazolidinones as potential anti-inflammatory agents: anti-inflammatory activity, soybean lipoxygenase inhibition effect and molecular docking studies. SAR QSAR Environ Res. 2022; 33(6): 485-497. https://doi.org/10.1080/1062936X.2022.2084772
Mahmood WAR, Aldabbagh AKA, Mahmoud MA. Synthesis and Characterization of New Benzothiazole-derived Schiff Bases Metal Complexes. Baghdad Sci J. 2022 Apr. 1 [cited 2023 Mar. 17]; 19(2): 0378. https://doi.org/10.21123/bsj.2022.19.2.0378
Nam MH, Park M, Park H, Kim Y, Yoon S, Sawant V S, et al. Indole-Substituted Benzothiazoles and Benzoxazoles as Selective and Reversible MAO-B Inhibitors for Treatment of Parkinson's Disease. ACS Chem Neurosci. 2017; 8(7): 1519-1529. https://doi.org/10.1021/acschemneuro.7b00050
Abdulfatai U, Uzairu A, Uba S. Molecular docking and quantitative structure-activity relationship study of anticonvulsant activity of aminobenzothiazole derivatives. Beni Suef Univ J Basic Appl Sci. 2018; 7, (2): 204-214. https://doi.org/10.1016/j.bjbas.2017.11.002.
Gao X, Liu J, Zuo X, Feng X, Gao Y. Recent Advances in Synthesis of Benzothiazole Compounds Related to Green Chemistry. Molecules. 2020 Apr 5; 25(7): 1675.DOI: 10.3390/molecules25071675. PMID: 32260500; PMCID: PMC7181030.
Djuidje EN, Barbari R, Baldisserotto A, Durini E, Sciabica S, Balzarini J, et al. Benzothiazole Derivatives as Multifunctional Antioxidant Agents for Skin Damage: Structure-Activity Relationship of a Scaffold Bearing a Five-Membered Ring System. Antioxidants (Basel). 2022 Feb 17; 11(2): 407. https://doi.org/10.3390/antiox11020407. PMID: 35204288; PMCID: PMC8869097.
Gill RK, Rawal RK, Bariwal J. Recent. Advances in the Chemistry and Biology of Benzothiazoles. Arch. Pharm. Chem. Life Sci. 2015; 348(3): 155-178. https://doi.org/10.1002/ardp.201400340
Nguyen T B. Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur. Monatsh Chem. 2020; 362 (17) :3448-3484. https://doi.org/10.1002/adsc.202000535
Hacıoğlu N, Güngör T, Tokay E, Önder, Ferah Cömert, Ay, Mehmet, Köçkar, Feray. Synthesis and biological evaluation of 2,4,6-trinitroaniline derivatives as potent antitumor agents. Monatshefte fur Chemie. 2020; 151: 1629–1641. https://doi.org/10.1007/s00706-020-02690-7
Alzubaidy SN, Yasin MA, lateef OA, Thamer HF. Synthesis, Characterization and study biologicalactivity of several 1-cyclopentene-1,2-dicarboxylimidyl Containing oxadiazole and Benzothiazole. Baghdad Sci J . 2014 Jun. 1; 11(2): 429-37. https://doi.org/10.21123/bsj.2014.11.2.429-437
Mohammed MH, chyad SI, Jabbar S.Abdul-Satar. Preparation, diagnostics, and biological evaluation of new1,3,4-thiadiazol derivatives. Mater Today Proc: 2022; 61(3): 710–716. https://doi.org/10.1016/j.matpr.2021.08.278. https://www.sciencedirect.com/science/article/pii/S2214785321057229
Quiroga EN, Sampietro AR, Vattuone MA. Screening anti-fungal activities of selected medicinal plants. J Ethnopharmacol .2001; 74: 89–96. https://doi.org/10.1016/S0378-8741(00)00350-0
Zheng X, Ma Z, Zhang D. Synthesis of Imidazole-Based Medicinal Molecules Utilizing the van Leusen Imidazole Synthesis. Pharmaceuticals (Basel). 2020; 13(3): 37. Published 2020 Mar 3. https://doi.org/10.3390/ph13030037
AlTamiemi EO, Khammas SJ, AlKaissi SS. Synthesis, Characterization and Study the Biological Activity of New Morpholine Derivative. Baghdad Sci J. 2015 Dec. 6; 12(4): 761-73. https://doi.org/10.21123/bsj.2015.12.4.761-773
Maged A, Ahamed LS. Synthesis of new heterocyclic derivatives from 2-furyl methanethiol and study their applications. Eurasian Chem Commun. 2021; 3(7): 461-476. https://doi.org/10.22034/ecc.2021.279489.1158
AL-Joubory AKJ, Abdullah LW, Mohammed AJ. Synthesis, Characterization and Biological Activity Evaluation of Some Pyrazoles, Thiazoles and Oxazoles Derived from 2-Mercaptoaniline. Baghdad Sci J. 2021 Mar. 30; 18(1(Suppl.): 0764. https://doi.org/10.21123/bsj.2021.18.1(Suppl.).0764
Ahamed LS, Ali RA, Ahmed RS. Solvent-free synthesis of new chalcone derivatives from 3-nitro phthalic acid and evaluation of their biological activities. Egypt J Chem. 2021; 64(6): 2963-2968. https://doi.org/10.21608/ejchem.2021.55742.3176
Hamzah MA, Jebur IK, Ahmed AK. Synthesis, Characterization and Biological Activity Evaluation of Some New Azo Derivatives from 2- Amino Benzothiazole and Their Derivatives. KUJSS. 2018; 13(1):219-224.
https://kujss.uokirkuk.edu.iq/article_143033.html
Al-hitti NF, Jebur Ikh. Synthesis and characterization of some new 2-mercapto benzimidazole derivative from ortho phenylenediamine. KUJSS. 2015; 10 (4):229-230.