Expedient Synthesis and Antitumor Evaluation of Novel Azaheterocycles from Thiazolylenaminone

References

• Samir Bondock, Omeer Albormani, Ahmed M. Fouda, and Kayed A. Abu Safieh, “Progress in the Chemistry of 5-Acetylthiazoles,” Synthetic Communications 46, no. 13 (2016): 1081–117.
   Web of Science ®Google Scholar
• Olesia G. Kulyk, Dmytro A. Biloborodov, Maksim A. Cherevatenko, Yevhen Y. Shyriakin, Alexander Yu Lyapunov, Alexander V. Mazepa, Valerii V. Vashchenko, Valeriy D. Orlov, and Maksim A. Kolosov, “Versatile Approaches to a Library of Building Blocks Based on 5-Acylthiazole Skeleton,” Synthetic Communications 50, no. 23 (2020): 3616–28.
   Web of Science ®Google Scholar
• Adileh Ayati, Saeed Emami, Setareh Moghimi, and Alireza Foroumadi, “Thiazole in the Targeted Anticancer Drug Discovery,” Future Medicinal Chemistry 11, no. 15 (2019): 1929–52.
   PubMed Web of Science ®Google Scholar
• Saqarkumar Patel Anuradha, Rajkumar Patle, Preethi Parameswaran, Alok Jain, and Amit Shard, “Design, Computational Studies, Synthesis and Biological Evaluation of Thiazole-Based Molecules as Anticancer Agents,” European Journal of Pharmaceutical Science 134 (2019): 20–30.
   PubMed Web of Science ®Google Scholar
• Samir Bondock, and Tamer Nasr, “Synthesis and Antimicrobial Activity of New 4-Methyl-2-(3-Pyridyl)Thiazolyl Chalcones and Pyrazolines,” Russian Journal of General Chemistry 91, no. 3 (2021): 488–94.
   Web of Science ®Google Scholar
• Samir Bondock, Tamer Naser, and Yousry A. Ammar, “Synthesis of Some New 2-(3-Pyridyl)-4,5-Disubstituted Thiazoles as Potent Antimicrobial Agents,” European Journal of Medicinal Chemistry 62 (2013): 270–9.
   PubMed Web of Science ®Google Scholar
• Anna Biernasiuk, Magdalena Kawczyńska, Anna Berecka-Rycerz, Beata Rosada, Anna Gumieniczek, Anna Malm, Katarzyna Dzitko, and Krzysztof Z. Łączkowski, “Synthesis, Antimicrobial Activity, and Determination of the Lipophilicity of ((Cyclohex-3-Enylmethylene)Hydrazinyl) Thiazole Derivatives,” Medicinal Chemistry Research 28, no. 11 (2019): 2023–36.
   Web of Science ®Google Scholar
• Dattatraya G. Raut, Sandeep B. Patil, Prafulla B. Choudhari, Vikas D. Kadu, Anjana S. Lawand, Mahesh G. Hublikar, and Raghunath B. Bhosale, “POCl3 Mediated Synthesis, Pharmacological Evaluation and Molecular Docking Studies of Some Novl Benzofused Thiazole Derivatives as a Potential Antioxidant and anti-Inflammatory Agents,” Current Chemical Biology 14, no. 1 (2020): 58–68.
   Google Scholar
• Salah A. Abdel-Aziz, Ehab S. Taher, Ping Lan, Gihan F. Asaad, Hesham A. M. Gomaa, Nawal A. El-Koussi, and Bahaa G. M. Youssif, “Design, Synthesis, and Biological Evaluation of New Pyrimidine-5-Carbonitrile Derivatives Bearing 1,3-Thiazole Moiety as Novel Anti-Inflammatory EGFR Inhibitors with Cardiac Safety Profile,” Bioorganic Chemistry 111 (2021): 104890.
   PubMed Web of Science ®Google Scholar
• Gajendra Kumar, and N. P. Singh, “Synthesis, Anti-Inflammatory and Analgesic Evaluation of Thiazole/Oxazole Substituted Benzothiazole Derivatives,” Bioorganic Chemistry 107 (2021): 104608.
   PubMed Web of Science ®Google Scholar
• Inder P. Singh, Shiv Gupta, and Sanjay Kumar, “Thiazole Compounds as Antiviral Agents: An Update,” Medicinal Chemistry (Shariqah (United Arab Emirates)) 16, no. 1 (2020): 4–23.
   PubMed Web of Science ®Google Scholar
• Sobhi M. Gomha, Khaled Khalil, Hassan Abdel-Aziz, and Mohamed Abdalla, “Synthesis and Antihypertensive α-Blocking Activity Evaluation of Thiazole Derivatives Bearing Pyrazole Moiety,” Heterocycles 91, no. 9 (2015): 1763–73.
   Web of Science ®Google Scholar
• Arpita Das, Surajit K. Ghosh, Hans R. Bhat, Junmoni Kalita, Ankita Kashyap, and Nayana Adhikari, “Docking, Synthesis and Antimalarial Evaluation of Hybrid Phenyl Thiazole 1,3,5-Triazene Derivatives,” Current Bioactive Compounds 16, no. 5 (2020): 639–53.
   Google Scholar
• Anthi Petrou, Maria Fesatidou, and Athina Geronikaki, “A Thiazole Ring – A Biologically Active Scaffold,” Molecules 26, no. 11 (2021): 3166.
   PubMed Web of Science ®Google Scholar
• Branko Stanovnik, and Jurij Svete, “Synthesis of Heterocycles from Alkyl 3-(Dimethylamino)Propenoates and Related Enaminones,” Chemical Reviews 104, no. 5 (2004): 2433–80.
   PubMed Web of Science ®Google Scholar
• Sayed M. Riyadh, “Enaminones as Building Blocks for the Synthesis of Substituted Pyrazoles with Antitumor and Antimicrobial Activities,” Molecules (Basel, Switzerland) 16, no. 2 (2011): 1834–53.
   PubMed Web of Science ®Google Scholar
• Hatem M. Gaber, Mark C. Bagley, Zeinab A. Muhammad, and Sobhi M. Gomha, “Recent Developments in Chemical Reactivity of N,N-Dimethylamino Ketones as Synthons for Various Heterocycles,” RSC Advances 7, no. 24 (2017): 14562–610.
   Web of Science ®Google Scholar
• Fathi A. Abu-Shanab, Sherif M. Sherif, and Sayed A. S. Mousa, “Dimethylformamide Dimethylacetal as Building Block in Heterocyclic Synthesis,” Journal of Heterocyclic Chemistry 46, no. 5 (2009): 801–27.
   Web of Science ®Google Scholar
• Mariam A. Al-Shiekh, Abdellatif M. Salah El-Din, Ebtisam H. Hafez, and Mohamed H. Elnagdi, “2-Arylhydrazono-3-Oxopropanals in Heterocyclic Synthesis: Synthesis of Arylazopyrazole, Arylazoisoxazole and Dialkylpyridazine-5,6-Dicarboxylate Derivatives. New One-Step Synthesis of Arylazopyrimidines,” Journal of Heterocyclic Chemistry 41, no. 5 (2004): 647–54.
   Web of Science ®Google Scholar
• Elsayed M. Afsah, El‐Sayed I. El‐Desoky, Hassan A. Etman, Ibrahim Youssef, and Ahbarah M. Soliman, “Mannich Reaction with Enaminones: Convenient Synthesis of Functionalized Tetrahydro-Pyrimidines, Dihydro-1,3-Oxazines, and Dihydro-1,2,4-Triazepines,” Journal of Heterocyclic Chemistry 55, no. 12 (2018): 2959–70.
   Web of Science ®Google Scholar
• Thoraya A. Farghaly, Alaa M. Abo Alnaja, and Mohamed R. Shaaban, “Recent Advances in Synthesis and Reactions of β-Amino-α,β-Enones (Enaminones),” Current Organic Synthesis 18, no. 7 (2021): 639–84.
   PubMed Web of Science ®Google Scholar
• Samir Bondock, and Ahmed M. Fouda, “Synthesis and Evaluation of Some New 5-(Hetaryl)Thiazoles as Potential Antimicrobial Agents,” Synthetic Communications 48, no. 5 (2018): 561–73.
   Web of Science ®Google Scholar
• Mostafa M. Ghorab, Mahmoud S. Bashandy, and Mansour S. Alsaid, “Novel Thiophene Derivatives with Sulfonamide, Isoxazole, Benzothiazole, Quinoline and Anthracene Moieties as Potential Anticancer Agents,” Acta Pharmaceutica (Zagreb, Croatia) 64, no. 4 (2014): 419–31.
   PubMed Web of Science ®Google Scholar
• Angela Casini, Andrea Scozzafava, Antonio Mastrolorenzo, and Laudiu T. Supuran, “Sulfonamides and Sulfonylated Derivatives as Anticancer Agents,” Current Cancer Drug Targets 2, no. 1 (2002): 55–75.
   PubMed Web of Science ®Google Scholar
• Mostafa M. Ghorab, Mansour S. Alsaid, Ghada H. Al-Ansary, Ghada A. Abdel-Latif, and Dalal A. Abou El Ella, “Analogue Based Drug Design, Synthesis, Molecular Docking and Anticancer Evaluation of Novel Chromene Sulfonamide Hybrids as Aromatase Inhibitors and Apoptosis Enhancers,” European Journal of Medicinal Chemistry 124 (2016): 946–58.
   PubMed Web of Science ®Google Scholar
• Assem Barakat, Saied M. Soliman, Matti Haukka, Abdullah Mohamed Al-Majid, Mohammed Shahidul Islam, M. Ali, and Mohammed Rafi Shaik, “One-Pot Synthesis, X-Ray Single Crystal and Molecular Insight of Enaminone-Based β-Morpholino-1N-Methylpiperazinyl-/Pyrrolidinyl Propiophenone,” Crystals 10, no. 4 (2020): 282.
   Google Scholar
• Florian Gagiu, Gyorgy Csavassy, and Greta Todor, “Synthesis of 2-Allylaminothiazoles,” Archiv der Pharmazie 300, no. 11 (1967): 964–8.
   Google Scholar
• Ahmad S. Shawali, and Adel J. M. Haboub, “Convenient Synthesis of Polyaza-3,4-Bis(Heteroaryl)Pyrazoles,” Synthetic Communications 45, no. 5 (2015): 611–24.
   Web of Science ®Google Scholar
• Antonio Salgado, Carmen Varela, Ana Maria Garcia Collazo, and Paolo Pevarello, “Differentiation Between [1,2,4]Triazolo[1,5-a]Pyrimidine and [1,2,4]Triazolo[4,3-a]-Pyrimidine Regioisomers by 1H–15N HMBC Experiments,” Magnetic Resonance in Chemistry: MRC 48, no. 8 (2010): 614–22.
   PubMed Web of Science ®Google Scholar
• Thoraya A. Farghaly, Naglaa A. Abdel Hafez, Eman A. Ragab, Hanem M. Awad, and Mohamed M. Abdalla, “Synthesis, Anti-HCV, Antioxidant, and Peroxynitrite Inhibitory Activity of Fused Benzosuberone Derivatives,” European Journal of Medicinal Chemistry 45, no. 2 (2010): 492–500.
   PubMed Web of Science ®Google Scholar
• Eberhard Breitmaier, Structure Elucidation by NMR in Organic Chemistry, A Practical Guide (Chichester, UK: John Wiley, 1993), 27.
   Google Scholar
• Philip Skehan, Ritsa Storeng, Dominic Scudiero, Anne Monks, James McMahon, David Vistica, Jonathan T. Warren, Heidi Bokesch, Susan Kenney, and Michael R. Boyd, “New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening,” Journal of the National Cancer Institute 82, no. 13 (1990): 1107–12.
   PubMed Web of Science ®Google Scholar
• Vanicha Vichai, and Kanyawim Kirtikara, “Sulforhodamine B Colorimetric Assay for Cytotoxicity Screening,” Nature Protocols 1, no. 3 (2006): 1112–6.
   PubMed Web of Science ®Google Scholar