تشييد بعض الهيدرازايد-هيدرازون والمركبات الحلقية غير المتجانسة الجديدة مشتقات الثايوفين ، ايمين ، كومارين و البيرازول

المؤلفون

  • استبرق محمد المولى قسم الكيمياء الصيدلانية، كلية الصيدلة، جامعة الموصل، موصل، العراق.
  • عمار حسين السبعاوي قسم الكيمياء، كلية العلوم، جامعة الموصل، موصل، العراق. https://orcid.org/0000-0002-8991-2991

DOI:

https://doi.org/10.21123/bsj.2024.9395

الكلمات المفتاحية:

كومارين ، مركبات حلقية غير متجانسة ، هيدرازيد –هيدرازون ، ايمين ، بيرازول ، ثايوفين.

الملخص

تم تشييد سلسلة من المشتقات الجديدة الثايوفين ، الايمين ، الكومارين و البيرازول X4-X16 باستخدام N – (1- (4- (بنزيل سلفونيل) فينيل) ايثيليدين)-2- سيانو اسيتو هيدرازيد X3 بوصفه مادة اساسية أولية عن طريق مفاعلتها مع كواشف مختلفة مثل (التترالون ، سايكلو بنتانون ، سايكلو هبتانون ، 2-هيدروكسي بنزالديهايد ، 2-هيدروكسي-1- نفثالديهايد ، كبريتيد ثنائي كاربون و فنيل ايزوثايو سيانيد). تم تحضير المركب X3 من تصعيد 4-(بنزايل سلفونيل) اسيتوفينون مع 2- سيانو اسيتوهيدرازايد في الايثانول. تم تشخيص تراكيب المركبات المحضرة الجديدة من خلال القياسات الفيزيائية و الطيفية (الأشعة تحت الحمراء والتحليل الطيفي البروتون والكاربون 13 النووي المغناطيسي).

المراجع

Boulebd H, Zine Y, Khodja I A, Mermer A, Demir A, Debache A. Synthesis and radical scavenging activity of new phenolic hydrazone/hydrazide derivatives: Experimental and theoretical studies. J Mol Struct. 2022; 1249: 131546. https://doi.org/10.1016/j.molstruc.2021.131546

Hassan RA, Al-Sabawi AH. Synthesis and Spectral Study of some New α, β-Unsaturated Carbonyl Compounds and Pyrazole Derivatives. Rafi J Sci. 2023; 32(1): 138-148. https://doi.org/10.33899/rjs.2023.177296

Mohammed SJ, Sheat AM, Abood SA, Yahya OM. Using Microwave and ultrasound to prepare of substituted Bis-acyl hydrazone Derivatives. Egypt J Chem. 2021; 64(11): 6423-6427. https://doi.org/10.21608/ejchem.2021.78532.3842

Şenkardeş S, Han MI, Kulabaş N, Abbak M, Çevik Ӧ, Küçükgüzel L, et al. Synthesis, molecular docking and evaluation of novel sulfonyl hydrazones as anticancer agents and COX-2 inhibitors. Mol Divers. 2020; 24: 673.

https://doi.org/10.1007/s11030-019-09974-z

Houssem B, Yasmine Z, Imene K, Arif M, Adem D, Abdelmadjid D. Synthesis and radical scavenging activity of new phenolic hydrazone/hydrazide derivatives: Experimental and theoretical studies. J Mol Struct. 2022; 1249(1): 131546.http://dx.doi.org/10.1016/j.molstruc.2021.131546

Łukasz P. Updated Information on Antimicrobial Activity of Hydrazide–Hydrazones. Int J Mol Sci. 2021; 22(9389): 1-20. https://doi.org/10.3390/ijms22179389

Thibaut B, Alexia B, Jérémy M, Cédric B, Floriane D, Anne B, et al. Synthesis and Biological Evaluation of Benzo[b]thiophene Acylhydrazones as Antimicrobial Agents against Multidrug-Resistant Staphylococcus aureus. Biomolecules. 2022; 12(1): 131.https://doi.org/10.3390%2Fbiom12010131

Altaee EA, Al-Sabawi AH. Synthesis and Spectral Study of Some New 4-substituted but-2-enolide Derivatives. Egypt J Chem. 2021. 64(12): 7117-7122. https://dx.doi.org/10.21608/ejchem.2021.80154.3957

Mishra R, Kumar N, Mishra I, Sachan N. A Review on Anticancer Activities of Thiophene and Its Analogs. Mini Rev Med Chem. 2020; 20(19): 1944-1965. https://dx.doi.org/10.2174/1389557520666200715104555.

Shah R, Verma PK. Therapeutic importance of synthetic thiophene. Chem Cent J. 2018. 12(1): 1-22. https://doi.org/10.1186/s13065-018-0511-5

Benabdellah M, Aouniti A, Dafali A, Hammouti B, Benkaddour M, Yahyi A, et al. nvestigation of the inhibitive effect of triphenyltin 2-thiophene carboxylate on corrosion of steel in 2 M H3PO4 solutions. Appl Surf Sci. 2006; 252(23): 8341-8347.https://doi.org/10.1016/j.apsusc.2005.11.037

Gao L, Wang F, Chen Y, Li F, Han B, Liu D. The antithrombotic activity of natural and synthetic coumarins. Fitoterapia. 2021; 154: 104947. https://doi.org/10.1016/j.fitote.2021.104947

Wang G, Sun S, Wu B, Liu J. Coumarins as Potential Anti-drug Resistant Cancer Agents: A Mini Review. Curr Top Med Chem. 2021; 21(19):1725-1736. https://doi.org/10.2174/1568026620999201113110041

Xu Z, Chen Q, Zhang Y, Liang C. Coumarin-based derivatives with potential anti-HIV activity. Fitoterapia. 2021; 150(104863): 1-10.https://doi.org/10.1016/j.fitote.2021.104863

Saleem M, Asif M, Parveen A, Yaseen HS, Saadullah M, Bashir A, et al. Investigation of in vivo anti-inflammatory and anti-angiogenic attributes of coumarin-rich ethanolic extract of Melilotus indicus. Inflammopharmacology. 2021; 29: 281-293. https://doi.org/10.1007/s10787-020-00703-9

Wang T, Peng T, Wen X, Wang G, Liu S, Sun Y, et al. Design, synthesis and evaluation of 3-substituted coumarin derivatives as anti-inflammatory agents. Chem Pharm Bull. 2020; 68(5): 443-446. https://doi.org/10.1248/cpb.c19-01085

Al-shahwany AG, Omer AO. Synthesis and study some new Schiff Bases derived from pyrazolo-coumarin. Raf J Sci. 2021; 30(1): 78-90 https://doi.org/10.33899/rjs.2021.167688

Kasperkiewicz K, Ponczek MB, Owczarek J, Guga P, Budzisz E. Antagonists of vitamin K—popular coumarin drugs and new synthetic and natural coumarin derivatives. Molecules. 2020; 25(6), 1465: 1-24. https://doi.org/10.3390/molecules25061465

Ansari A, Ali A, Asif M. Biologically active pyrazole derivatives. New J Chem. 2017; 41(1): 16-41. https://doi.org/10.1039/C6NJ03181A

Ahmood J, Layth W, Abdullah J. Synthesis, Characterization and Biological ActivityEvaluationof Some Pyrazoles, Thiazoles and Oxazoles Derived from 2-Mercaptoaniline. Baghdad Sci J. 2021; 18(1): 764-774. https://doi.org/10.21123/bsj.2021.18.1(Suppl.).0764

Hosny MA, Zaki YH, Mokbel WA, Abdelhamid AO. Synthesis, Characterization, Antimicrobial Activity and Anticancer of Some New Pyrazolo[1,5-a]pyrimidines and Pyrazolo[5,1-c]1,2,4-triazines. Med Chem. 2020; 16(6): 750-760.https://doi.org/10.2174/1573406415666190620144404

Wissam K, Kadir AM, Ibtisam K. Synthesis and characterization of some heterocyclic including oxazoles,Thiazoles, Pyridazines, phthalizines and Pyrazoles with evaluating of biological activity. Baghdad Sci J. 2013; 10(3): 818-827. https://doi.org/10.21123/bsj.2013.10.3.818-827

Zárate-Zárate D, Aguilar R, Hernández-Benitez RI, Labarrios EM, Delgado F, Tamariz J. Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products. Tetrahedron. 2015; 71(38): 6961-6978. https://doi.org/10.1016/j.tet.2015.07.010

Alsayari A, Asiri YI, Bin Muhsinah A, Hassan MZ. Synthesis of New Pyrazole Hybrids as Potential Anticancer Agents with Xanthine Oxidase Inhibitory Activity. Anticancer Agents Med Chem. 2022; 22(12): 2303-2309. https://doi.org/10.2174/1871520622666220110162651

Payne M, Bottomley A L, Och A, Asmara A P, Harry E J, Ung AT. Synthesis and biological evaluation of 3, 5-substituted pyrazoles as possible antibacterial agents. Bioorg Med Chem. 2021; 48: 116401. https://doi.org/10.1016/j.bmc.2021.116401

Nidhar M, Khanam S, Sonker P, Gupta P, Mahapatra A, Patil S, et al. Click inspired novel pyrazole-triazole-persulfonimide & pyrazole-triazole-aryl derivatives; Design, synthesis, DPP-4 inhibitor with potential anti-diabetic agents. Bioorg Chem. 2022; 120 :105586. https://doi.org/10.1016/j.bioorg.2021.105586

Hassan R A, Al-Sabawi A.H. Synthesis of Some New α, β-Unsaturated Carbonyl Compounds, Thiophene, Imine and Coumarin Derivatives Containing Hydrazide-Hydrazone Moiety. Egyp J Chem. 2023; 66(6): 383-391.https://dx.doi.org/10.21608/ejchem.2022.156323.6764

Al-Sabawi A.H, Younis S.A, Saeed RA. Synthesis of Some Novel Pyridine, Sulfonamide, Coumarin and Thiophene Derivatives. Egyp J Chem. 2023; 66(2): 349-355. https://doi.org/10.21608/ejchem.2022.135732.5979

Khidre RE, El‐Gogary SR, Mostafa MS. Design, synthesis, and antimicrobial evaluation of some novel pyridine, coumarin, and thiazole derivatives. J Heterocycl Chem. 2017; 54(4): 2511-2519. https://doi.org/10.1002/jhet.2854

Salman AS. Utility of activated nitriles in the synthesis of novel heterocyclic compounds with antitumor activity. Org Chem Int. 2013; 1-9 https://dx.doi.org/10.1155/2013/259348

Özkay Y, Tunalı Y, Karaca H, Işıkdağ I. Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety. Eur J Med Chem. 2010; 45(8): 3293-3298. https://doi.org/10.1016/j.ejmech.2010.04.012

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كيفية الاقتباس

1.
تشييد بعض الهيدرازايد-هيدرازون والمركبات الحلقية غير المتجانسة الجديدة مشتقات الثايوفين ، ايمين ، كومارين و البيرازول. Baghdad Sci.J [انترنت]. [وثق 27 سبتمبر، 2024];22(3). موجود في: https://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/9395