Research Article
Bazı Yeni 1,2,3-Triazol-arilidenhidrazid Hibrit Bileşiklerinin Sentezi ve Anti-mikrobiyal Etkinliklerinin Belirlenmesi
Abstract
Günümüzde kansere ve diğer mikroorganizmalara karşı kullanılan ilaçların pek çoğunun
biyoyararlanımının düşük olması ve başta toksisite gibi yan etkilerinden dolayı tedavide yeni
ilaçların varlığına ihtiyaç duyulmaktadır. Her gün artan sayıda anti-kanser veya antibiyotik
ilaç geliştirilmesine rağmen, bu ilaçların seçiciliklerinin düşük olması ve çoklu ilaç
direncinin kazanılması, başarılı bir tedavinin önüne geçmektedir. Bu nedenle, tümör
hücrelerini veya mikroorganizmaları yok etmek veya en azından çoğalmasını durdurmak için
yeni, güçlü ve seçici ajanlarının keşfine önemli ölçüde ihtiyaç duyulmaktadır. Bu çalışma
kapsamında 18 adet yeni 1,2,3-triazol/arilidenhidrazid yapısında hibrit bileşik sentezlendi.
Elde edilen 18 yeni bileşiğin (17a-r) Staphylococcus Aureus ve Escheric1hia coli bakteri
türleri ve Candida albicans mantar türü üzerindeki anti-mikrobiyal etkinlikleri araştırıldı.
Elde edilen sonuçlar anti-mikrobiyal ilaç seftazidim ile karşılaştırıldı. Bileşiklerin anti fungal
etkinliklerinin MİK değerleri 62.5 μM olarak bulunurken anti-bakteriyel etkinliklerinin MİK
değerleri 62.5-125 μM olarak belirlendi.
Supporting Institution
TÜBİTAK
Project Number
2209A - 1919B012100494
References
- Aparna, Y., Nirmala, G., Subhashini, N. J. P., Sharada, L. N. ve Sreekanth, S. (2020). Synthesis and Antimicrobial Activity of Novel Bis-1,2,3-triazol-1H-4-yl-substituted Aryl Benzimidazole-2-thiol Derivatives. Russian Journal of General Chemistry, 90 (8), 1501-1506.
- Bayrak, C., Senol, H., Sirtbasi, S., Sahin, E. ve Menzek, A. (2018). Synthesis and rearrangement reactions of 1,4-dihydrospiro[1,4-methanonaphthalene-9,1 '-cyclopropane] derivatives. Tetrahedron, 74 (40), 5839-5849.
- Cardoso, C. S., Silva, D. P. B., Silva, D. M., Fiorentino, I. F., Fajemiroye, J. O., Moreira, L. K. S., Vasconcelos, J. P., Sanz, G., Vaz, B. G., Liao, L. M., Lima, D. D., Dos Santos, F. C. A., Menegatti, R. ve Costa, E. A. (2020). Mechanisms involved in the antinociceptive and anti-inflammatory effects of a new triazole derivative: 5- 1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl -1H-tetrazole (LQFM-096). Inflammopharmacology, 28 (4), 877-892.
- Colin, S., Chinetti-Gbaguidi, G., Kuivenhoven, J. A. ve Staels, B. (2015). Emerging Small Molecule Drugs. High Density Lipoproteins: from Biological Understanding to Clinical Exploitation, 224, 617-630.
- Cramer, J., Schiebel, J., Wulsdorf, T., Grohe, K., Najbauer, E. E., Ehrmann, F. R., Radeva, N., Zitzer, N., Linne, U., Linser, R., Heine, A. ve Klebe, G. (2017). A False-Positive Screening Hit in Fragment-Based Lead Discovery: Watch out for the Red Herring. Angewandte Chemie-International Edition, 56 (7), 1908-1913.
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- De Fusco, C., Brear, P., Iegre, J., Georgiou, K. H., Sore, H. F., Hyvonen, M. ve Spring, D. R. (2017). A fragment-based approach leading to the discovery of a novel binding site and the selective CK2 inhibitor CAM4066. Bioorg Med Chem, 25 (13), 3471-3482.
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- Judge, V., Narasimhan, B., Ahuja, M., Sriram, D., Yogeeswari, P., De Clercq, E., Pannecouque, C. ve Balzarini, J. (2012). Isonicotinic acid hydrazide derivatives: synthesis, antimicrobial activity, and QSAR studies. Medicinal Chemistry Research, 21 (7), 1451-1470.
- Judge, V., Narasimhan, B., Ahuja, M., Sriram, D., Yogeeswari, P., De Clercq, E., Pannecouque, C. ve Balzarini, J. (2013). Synthesis, Antimycobacterial, Antiviral, Antimicrobial Activity and QSAR Studies of N-2-acyl isonicotinic Acid Hydrazide Derivatives. Medicinal Chemistry, 9 (1), 53-76.
- Kaushik, C. P. ve Luxmi, R. (2017). Synthesis and Antimicrobial Activity of 2-(4-(Hydroxyalkyl)-1H-1,2,3-triazol-1-yl)-N-substituted propanamides. Journal of Heterocyclic Chemistry, 54 (6), 3618-3625.
- Kaushik, C. P., Pahwa, A., Kumar, D., Kumar, A., Singh, D., Kumar, K. ve Luxmi, R. (2018). Synthesis and Antimicrobial Evaluation of (1-(2-(Benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl Benzoate Analogues. Journal of Heterocyclic Chemistry, 55 (7), 1720-1728.
- Kaya, B., Kaplancıklı, Z. A., Yurttaş, L. ve Çiftçi, G. A. (2017). Synthesis and biological evaluation of some new pyrimidine bearing 2,5-disubstituted 1,3,4-oxadiazole derivatives as cytotoxic agents. Turkish Journal of Biochemistry, 42 (2), 131-137.
- Krolenko, K. Y., Vlasov, S. V. ve Zhuravel, I. A. (2016). Synthesis and antimicrobial activity of 5-(1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazole derivatives. Chemistry of Heterocyclic Compounds, 52 (10), 823-830.
- Kumar, D., Kumar, N. M., Ghosh, S. ve Shah, K. (2012). Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents. Bioorganic & Medicinal Chemistry Letters, 22 (1), 212-215.
- Kumar, K. S., Mohanty, S., Reddy, G. P., Siddaiah, V., Lilakar, J. D. ve Goud, G. L. (2019). Synthesis and Antimicrobial Activity of 3-{2- (1-Aryl-1H-1,2,3-triazol-4-yl)methoxy -5-fluorophenyl}isoxazoles. Russian Journal of General Chemistry, 89 (6), 1221-1224.
- Kumar, S., Sharma, B., Mehra, V. ve Kumar, V. (2021). Recent accomplishments on the synthetic/biological facets of pharmacologically active 1H-1,2,3-triazoles. European Journal of Medicinal Chemistry, 212, 113069.
- Lal, K., Yadav, P. ve Kumar, A. (2016). Synthesis, characterization and antimicrobial activity of 4-((1-benzyl/phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde analogues. Medicinal Chemistry Research, 25 (4), 644-652. Liu, C. Y., Bian, M., Yu, L. J. ve Wei, C. X. (2018). Synthesis and Anti-Inflammatory Activity Evaluation of 5-(1-Benzyl-1H- 1,2,3 Triazol-4-yl)-4-Phenyl-4H- 1,2,4 Triazole-3-Thiol Derivatives. Indian Journal of Pharmaceutical Education and Research, 52 (3), 505-513.
- Lu, B. S. ve Atala, A. (2014). Small molecules and small molecule drugs in regenerative medicine. Drug Discovery Today, 19 (6), 801-808.
- Mallah, N., Orsini, N., Figueiras, A. ve Takkouche, B. (2022). Education level and misuse of antibiotics in the general population: a systematic review and dose-response meta-analysis. Antimicrobial Resistance and infection control, 11 (1), 24-46.
- Meunier, B. (2008). Hybrid molecules with a dual mode of action: Dream or reality? Accounts of Chemical Research, 41 (1), 69-77.
- Mohamed, N. A. (2019). Antimicrobial itaconimido aromatic hydrazide derivatives for inhibition of the thermal degradation of rigid PVC. Polymer Bulletin, 76 (5), 2341-2365.
- Mohamed, N. A. ve Abd El-Ghany, N. A. (2017). Synthesis, characterization, and antimicrobial activity of chitosan hydrazide derivative. International Journal of Polymeric Materials and Polymeric Biomaterials, 66 (8), 410-415.
- Moningka, R., Romero, F. A., Hastings, N. B., Guo, Z. Q., Wang, M., Di Salvo, J., Li, Y., Trusca, D., Deng, Q. L., Tong, V., Terebetski, J. L., Ball, R. G. ve Ujjainwalla, F. (2020). Fragment-based lead discovery of a novel class of small molecule antagonists of neuropeptide B/W receptor subtype 1 (GPR7). Bioorganic & Medicinal Chemistry Letters, 30 (23), 127510.
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- O'driscoll, C. (2019). Better, safer, small molecule drugs. Chemistry & Industry, 83 (7), 11-11.
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- Steinhagen, H. (2016). Igniting Small-Molecule Drug Discovery. Chemmedchem, 11 (2), 148-149.
- Subhashini, N. J. P., Boddu, L., Amanaganti, J. ve Shivaraj. (2014). Synthesis, characterization, and antimicrobial activity of new bis-1,2,3-triazol-H-yl-substituted 2-arylbenzimidazoles. Russian Journal of General Chemistry, 84 (7), 1442-1449. Şenol, H., Bayrak, C., Menzek, A., Sahin, E. ve Karakus, M. (2016). Cycloaddition reaction of spiro[2.4]hepta-4,6-dien-1-ylmethanol and PTAD: a new rearrangement. Tetrahedron, 72 (20), 2587-2592.
- Şenol, H., Mercümek, B., Şahin, R. B., Kapucu, H. B. ve Hacıosmanoğlu, E. (2022a). Synthesis of oleanolic acid hydrazide-hydrazone hybrid derivatives and investigation of their cytotoxic effects on A549 human lung cancer cells. Results in Chemistry, 4, 100317.
- Şenol, H., Şahin, R. B., Mercümek, B., Kapucu, H. B., Hacıosmanoğlu, E., Dinç, H. ve Yüksel Mayda, P. (2022b). Synthesis of ursolic acid arylidene-hydrazide hybrid compounds and investigation of their cytotoxic and antimicrobial effects. Natural Product Research, 11, 1-8.
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Synthesis of Some New 1,2,3-Triazole-Arylidenehydrazide Hybrid Compounds and Determination of Their Antimicrobial Activities
Abstract
At the present time, due to the low bioavailability of many of the drugs used against cancer
and other microorganisms and their side effects such as toxicity, there is a need for new
drugs in the treatment. Although an increasing number of anticancer or antibiotic drugs are
being developed every day, the low selectivity of these drugs and the acquisition of multidrug
resistance prevent successful treatment. Therefore, there is a great need for the
discovery of new, potent and selective agents to destroy or at least stop the proliferation of
tumor cells or microorganisms. In this study, 18 new 1,2,3-triazole/arylidenehydrazide
hybrid compounds were synthesized. Anti-microbial activities of these compounds (17a-r)
were investigated on Staphylococcus Aureus and Escherichia coli and Candida albicans.
The results were compared with the anti-microbial drug ceftazidime. The MIC values of the
anti-fungal activities of the compounds were found as 62.5 μM, while the MIC values of the
anti-bacterial activities were determined as 62.5-125 μM.
Project Number
2209A - 1919B012100494
References
- Aparna, Y., Nirmala, G., Subhashini, N. J. P., Sharada, L. N. ve Sreekanth, S. (2020). Synthesis and Antimicrobial Activity of Novel Bis-1,2,3-triazol-1H-4-yl-substituted Aryl Benzimidazole-2-thiol Derivatives. Russian Journal of General Chemistry, 90 (8), 1501-1506.
- Bayrak, C., Senol, H., Sirtbasi, S., Sahin, E. ve Menzek, A. (2018). Synthesis and rearrangement reactions of 1,4-dihydrospiro[1,4-methanonaphthalene-9,1 '-cyclopropane] derivatives. Tetrahedron, 74 (40), 5839-5849.
- Cardoso, C. S., Silva, D. P. B., Silva, D. M., Fiorentino, I. F., Fajemiroye, J. O., Moreira, L. K. S., Vasconcelos, J. P., Sanz, G., Vaz, B. G., Liao, L. M., Lima, D. D., Dos Santos, F. C. A., Menegatti, R. ve Costa, E. A. (2020). Mechanisms involved in the antinociceptive and anti-inflammatory effects of a new triazole derivative: 5- 1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl -1H-tetrazole (LQFM-096). Inflammopharmacology, 28 (4), 877-892.
- Colin, S., Chinetti-Gbaguidi, G., Kuivenhoven, J. A. ve Staels, B. (2015). Emerging Small Molecule Drugs. High Density Lipoproteins: from Biological Understanding to Clinical Exploitation, 224, 617-630.
- Cramer, J., Schiebel, J., Wulsdorf, T., Grohe, K., Najbauer, E. E., Ehrmann, F. R., Radeva, N., Zitzer, N., Linne, U., Linser, R., Heine, A. ve Klebe, G. (2017). A False-Positive Screening Hit in Fragment-Based Lead Discovery: Watch out for the Red Herring. Angewandte Chemie-International Edition, 56 (7), 1908-1913.
- Davis, B. J. ve Roughley, S. D., 2017. Fragment-Based Lead Discovery. Annual Reports in Medicinal Chemistry, Vol 50: Platform Technologies in Drug Discovery and Validation ed., Ed: R.A. Goodnow. Annual Reports in Medicinal Chemistry, 371-439.
- De Fusco, C., Brear, P., Iegre, J., Georgiou, K. H., Sore, H. F., Hyvonen, M. ve Spring, D. R. (2017). A fragment-based approach leading to the discovery of a novel binding site and the selective CK2 inhibitor CAM4066. Bioorg Med Chem, 25 (13), 3471-3482.
- Dickson, M. ve Gagnon, J. P. (2004). Key factors in the rising cost of new drug discovery and development. Nature Reviews Drug Discovery, 3 (5), 417-429.
- Dimasi, J. A., Hansen, R. W. ve Grabowski, H. G. (2003). The price of innovation: new estimates of drug development costs. Journal of Health Economics, 22 (2), 151-185.
- Dogan, H. N., Rollas, S. ve Erdeniz, H. (1998). Synthesis, structure elucidation and antimicrobial activity of some 3-hydroxy-2-naphthoic acid hydrazide derivatives. Farmaco, 53 (7), 462-467.
- El-Sayed, H. A., Moustafa, A. H., Abd El-Moneim, M., Awad, H. M. ve Esmat, A. (2018). A new series of hydrazide-hydrazones based 2-oxonicotinonitriles as antimicrobial agents: Design, synthesis and antimicrobial evaluation. Afinidad, 75 (584), 305-310.
- Frutos, R. P., Rodriguez, S., Patel, N. D., Reeves, D., Tampone, T. ve Senanayake, C. H. (2014). A General and Practical Synthesis of N-Aryl-3- 4-(imidazol-4-yl)-1,2,3-triazol-1-yl benzamide Anti-Inflammatory Cytokine Inhibitors. Asian Journal of Organic Chemistry, 3 (7), 769-772.
- Jain, R., Gahlyan, P., Dwivedi, S., Konwar, R., Kumar, S., Bhandari, M., Arora, R., Kakkar, R., Kumar, R. ve Prasad, A. K. (2018). Design, Synthesis and Evaluation of 1H-1,2,3-Triazol-4-yl-methyl Tethered 3-Pyrrolylisatins as Potent Anti-Breast Cancer Agents. Chemistryselect, 3 (19), 5263-5268.
- Jardim, D. L., Schwaederle, M., Hong, D. S. ve Kurzrock, R. (2016). An appraisal of drug development timelines in the Era of precision oncology. Oncotarget, 7 (33), 53037-53046.
- Judge, V., Narasimhan, B., Ahuja, M., Sriram, D. ve Yogeeswari, P. (2011). Isonicotinic Acid Hydrazide Derivatives: Synthesis, Antimycobacterial, Antiviral, Antimicrobial Activity and QSAR Studies. Letters in Drug Design & Discovery, 8 (9), 792-810.
- Judge, V., Narasimhan, B., Ahuja, M., Sriram, D., Yogeeswari, P., De Clercq, E., Pannecouque, C. ve Balzarini, J. (2012). Isonicotinic acid hydrazide derivatives: synthesis, antimicrobial activity, and QSAR studies. Medicinal Chemistry Research, 21 (7), 1451-1470.
- Judge, V., Narasimhan, B., Ahuja, M., Sriram, D., Yogeeswari, P., De Clercq, E., Pannecouque, C. ve Balzarini, J. (2013). Synthesis, Antimycobacterial, Antiviral, Antimicrobial Activity and QSAR Studies of N-2-acyl isonicotinic Acid Hydrazide Derivatives. Medicinal Chemistry, 9 (1), 53-76.
- Kaushik, C. P. ve Luxmi, R. (2017). Synthesis and Antimicrobial Activity of 2-(4-(Hydroxyalkyl)-1H-1,2,3-triazol-1-yl)-N-substituted propanamides. Journal of Heterocyclic Chemistry, 54 (6), 3618-3625.
- Kaushik, C. P., Pahwa, A., Kumar, D., Kumar, A., Singh, D., Kumar, K. ve Luxmi, R. (2018). Synthesis and Antimicrobial Evaluation of (1-(2-(Benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl Benzoate Analogues. Journal of Heterocyclic Chemistry, 55 (7), 1720-1728.
- Kaya, B., Kaplancıklı, Z. A., Yurttaş, L. ve Çiftçi, G. A. (2017). Synthesis and biological evaluation of some new pyrimidine bearing 2,5-disubstituted 1,3,4-oxadiazole derivatives as cytotoxic agents. Turkish Journal of Biochemistry, 42 (2), 131-137.
- Krolenko, K. Y., Vlasov, S. V. ve Zhuravel, I. A. (2016). Synthesis and antimicrobial activity of 5-(1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazole derivatives. Chemistry of Heterocyclic Compounds, 52 (10), 823-830.
- Kumar, D., Kumar, N. M., Ghosh, S. ve Shah, K. (2012). Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents. Bioorganic & Medicinal Chemistry Letters, 22 (1), 212-215.
- Kumar, K. S., Mohanty, S., Reddy, G. P., Siddaiah, V., Lilakar, J. D. ve Goud, G. L. (2019). Synthesis and Antimicrobial Activity of 3-{2- (1-Aryl-1H-1,2,3-triazol-4-yl)methoxy -5-fluorophenyl}isoxazoles. Russian Journal of General Chemistry, 89 (6), 1221-1224.
- Kumar, S., Sharma, B., Mehra, V. ve Kumar, V. (2021). Recent accomplishments on the synthetic/biological facets of pharmacologically active 1H-1,2,3-triazoles. European Journal of Medicinal Chemistry, 212, 113069.
- Lal, K., Yadav, P. ve Kumar, A. (2016). Synthesis, characterization and antimicrobial activity of 4-((1-benzyl/phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde analogues. Medicinal Chemistry Research, 25 (4), 644-652. Liu, C. Y., Bian, M., Yu, L. J. ve Wei, C. X. (2018). Synthesis and Anti-Inflammatory Activity Evaluation of 5-(1-Benzyl-1H- 1,2,3 Triazol-4-yl)-4-Phenyl-4H- 1,2,4 Triazole-3-Thiol Derivatives. Indian Journal of Pharmaceutical Education and Research, 52 (3), 505-513.
- Lu, B. S. ve Atala, A. (2014). Small molecules and small molecule drugs in regenerative medicine. Drug Discovery Today, 19 (6), 801-808.
- Mallah, N., Orsini, N., Figueiras, A. ve Takkouche, B. (2022). Education level and misuse of antibiotics in the general population: a systematic review and dose-response meta-analysis. Antimicrobial Resistance and infection control, 11 (1), 24-46.
- Meunier, B. (2008). Hybrid molecules with a dual mode of action: Dream or reality? Accounts of Chemical Research, 41 (1), 69-77.
- Mohamed, N. A. (2019). Antimicrobial itaconimido aromatic hydrazide derivatives for inhibition of the thermal degradation of rigid PVC. Polymer Bulletin, 76 (5), 2341-2365.
- Mohamed, N. A. ve Abd El-Ghany, N. A. (2017). Synthesis, characterization, and antimicrobial activity of chitosan hydrazide derivative. International Journal of Polymeric Materials and Polymeric Biomaterials, 66 (8), 410-415.
- Moningka, R., Romero, F. A., Hastings, N. B., Guo, Z. Q., Wang, M., Di Salvo, J., Li, Y., Trusca, D., Deng, Q. L., Tong, V., Terebetski, J. L., Ball, R. G. ve Ujjainwalla, F. (2020). Fragment-based lead discovery of a novel class of small molecule antagonists of neuropeptide B/W receptor subtype 1 (GPR7). Bioorganic & Medicinal Chemistry Letters, 30 (23), 127510.
- Mutagonda, R. F., Marealle, A. I., Nkinda, L., Kibwana, U., Maganda, B. A., Njiro, B. J., Ndumwa, H. P., Kilonzi, M., Mikomangwa, W. P., Mlyuka, H. J., Felix, F. F., Myemba, D. T., Mwakawanga, D. L., Sambayi, G., Kunambi, P. P., Ndayishimiye, P., Sirili, N., Mfaume, R., Nshau, A., Nyankesha, E., Scherpbier, R. ve Bwire, G. M. (2022). Determinants of misuse of antibiotics among parents of children attending clinics in regional referral hospitals in Tanzania. Scientific Reports, 12 (1).
- Narang, R., Narasimhan, B., Sharma, S., Sriram, D., Yogeeswari, P., De Clercq, E., Pannecouque, C. ve Balzarini, J. (2012). Synthesis, antimycobacterial, antiviral, antimicrobial activities, and QSAR studies of nicotinic acid benzylidene hydrazide derivatives. Medicinal Chemistry Research, 21 (8), 1557-1576.
- O'driscoll, C. (2019). Better, safer, small molecule drugs. Chemistry & Industry, 83 (7), 11-11.
- Refat, H. M. ve Fadda, A. A. (2013). Synthesis and antimicrobial activity of some novel hydrazide, benzochromenone, dihydropyridine, pyrrole, thiazole and thiophene derivatives. European Journal of Medicinal Chemistry, 70, 419-426.
- Steinhagen, H. (2016). Igniting Small-Molecule Drug Discovery. Chemmedchem, 11 (2), 148-149.
- Subhashini, N. J. P., Boddu, L., Amanaganti, J. ve Shivaraj. (2014). Synthesis, characterization, and antimicrobial activity of new bis-1,2,3-triazol-H-yl-substituted 2-arylbenzimidazoles. Russian Journal of General Chemistry, 84 (7), 1442-1449. Şenol, H., Bayrak, C., Menzek, A., Sahin, E. ve Karakus, M. (2016). Cycloaddition reaction of spiro[2.4]hepta-4,6-dien-1-ylmethanol and PTAD: a new rearrangement. Tetrahedron, 72 (20), 2587-2592.
- Şenol, H., Mercümek, B., Şahin, R. B., Kapucu, H. B. ve Hacıosmanoğlu, E. (2022a). Synthesis of oleanolic acid hydrazide-hydrazone hybrid derivatives and investigation of their cytotoxic effects on A549 human lung cancer cells. Results in Chemistry, 4, 100317.
- Şenol, H., Şahin, R. B., Mercümek, B., Kapucu, H. B., Hacıosmanoğlu, E., Dinç, H. ve Yüksel Mayda, P. (2022b). Synthesis of ursolic acid arylidene-hydrazide hybrid compounds and investigation of their cytotoxic and antimicrobial effects. Natural Product Research, 11, 1-8.
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There are 43 citations in total.
Details
| Primary Language | Turkish |
|---|---|
| Subjects | Chemical Engineering |
| Journal Section | Kimya / Chemistry |
| Authors | |
| Project Number | 2209A - 1919B012100494 |
| Early Pub Date | February 24, 2023 |
| Publication Date | March 1, 2023 |
| Submission Date | September 20, 2022 |
| Acceptance Date | November 14, 2022 |
| Published in Issue | Year 2023 Volume: 13 Issue: 1 |
