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Research Article

Synthesis of mono Mannich bases of 2-(4-hydroxybenzylidene)-2,3-dihydroinden-1-one and evaluation of their cytotoxicities

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Pages 818-823 | Received 11 Feb 2015, Accepted 25 Jun 2015, Published online: 06 Aug 2015

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (14)

Miao-Xia Pu, Hong-Yan Guo, Zhe-Shan Quan, Xiaoting Li & Qing-Kun Shen. (2023) Application of the Mannich reaction in the structural modification of natural products. Journal of Enzyme Inhibition and Medicinal Chemistry 38:1.
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Run-Hui Zhang, Hong-Yan Guo, Hao Deng, Jinzi Li & Zhe-Shan Quan. (2021) Piperazine skeleton in the structural modification of natural products: a review. Journal of Enzyme Inhibition and Medicinal Chemistry 36:1, pages 1165-1197.
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Anu Rani, Amit Anand, Kewal Kumar & Vipan Kumar. (2019) Recent developments in biological aspects of chalcones: the odyssey continues. Expert Opinion on Drug Discovery 14:3, pages 249-288.
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Sinan Bilginer, Halise Inci Gul, Feyza Sena Erdal, Hiroshi Sakagami, Serkan Levent, Ilhami Gulcin & Claudiu T. Supuran. (2019) Synthesis, cytotoxicities, and carbonic anhydrase inhibition potential of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones. Journal of Enzyme Inhibition and Medicinal Chemistry 34:1, pages 1722-1729.
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Halise Inci Gul, Cem Yamali, Fatma Yesilyurt, Hiroshi Sakagami, Kaan Kucukoglu, Ilhami Gulcin, Mustafa Gul & Claudiu T. Supuran. (2017) Microwave-assisted synthesis and bioevaluation of new sulfonamides. Journal of Enzyme Inhibition and Medicinal Chemistry 32:1, pages 369-374.
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Halise Inci Gul, Ebru Mete, Parham Taslimi, Ilhami Gulcin & Claudiu T. Supuran. (2017) Synthesis, carbonic anhydrase I and II inhibition studies of the 1,3,5-trisubstituted-pyrazolines . Journal of Enzyme Inhibition and Medicinal Chemistry 32:1, pages 189-192.
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Halise Inci Gul, Ebru Mete, Sakip Emre Eren, Hiroshi Sakagami, Cem Yamali & Claudiu T. Supuran. (2017) Designing, synthesis and bioactivities of 4-[3-(4-hydroxyphenyl)-5-aryl-4,5-dihydro-pyrazol-1-yl]benzenesulfonamides. Journal of Enzyme Inhibition and Medicinal Chemistry 32:1, pages 169-175.
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Cem Yamali, Halise Inci Gul, Hiroshi Sakagami & Claudiu T. Supuran. (2016) Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases. Journal of Enzyme Inhibition and Medicinal Chemistry 31:sup4, pages 125-131.
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Kaan Kucukoglu, Fatih Oral, Tevfik Aydin, Cem Yamali, Oztekin Algul, Hiroshi Sakagami, Ilhami Gulcin, Claudiu T. Supuran & Halise Inci Gul. (2016) Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines. Journal of Enzyme Inhibition and Medicinal Chemistry 31:sup4, pages 20-24.
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Elif Unluer, Halise Inci Gul, Alkan Demirtas, Hiroshi Sakagami, Naoki Umemura, Muhammet Tanc, Cavit Kazaz & Claudiu T. Supuran. (2016) Synthesis and bioactivity studies of 1-aryl-3-(2-hydroxyethylthio)-1-propanones. Journal of Enzyme Inhibition and Medicinal Chemistry 31:sup3, pages 105-109.
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Halise Inci Gul, Zehra Yazici, Muhammet Tanc & Claudiu T. Supuran. (2016) Inhibitory effects of benzimidazole containing new phenolic Mannich bases on human carbonic anhydrase isoforms hCA I and II. Journal of Enzyme Inhibition and Medicinal Chemistry 31:6, pages 1540-1544.
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Dilan Ozmen Ozgun, Cem Yamali, Halise Inci Gul, Parham Taslimi, Ilhami Gulcin, Telat Yanik & Claudiu T. Supuran. (2016) Inhibitory effects of isatin Mannich bases on carbonic anhydrases, acetylcholinesterase, and butyrylcholinesterase. Journal of Enzyme Inhibition and Medicinal Chemistry 31:6, pages 1498-1501.
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Halise Inci Gul, Cem Yamali, Asiye Tugce Yasa, Elif Unluer, Hiroshi Sakagami, Muhammet Tanc & Claudiu T. Supuran. (2016) Carbonic anhydrase inhibition and cytotoxicity studies of Mannich base derivatives of thymol. Journal of Enzyme Inhibition and Medicinal Chemistry 31:6, pages 1375-1380.
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Cem Yamali, Mehtap Tugrak, Halise Inci Gul, Muhammet Tanc & Claudiu T. Supuran. (2016) The inhibitory effects of phenolic Mannich bases on carbonic anhydrase I and II isoenzymes. Journal of Enzyme Inhibition and Medicinal Chemistry 31:6, pages 1678-1681.
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Cem Yamali, Sedat Sevin, Merve Nenni, Mehtap Tugrak Sakarya, Recep Uyar, Abdurrahman Aygul, Mahmut Ulger, Recep Ilhan, Serkan Levent & Halise Inci Gul. (2023) Design, synthesis, and assessment of pharmacological properties of indole-based fluorinated chalcones and their benzenesulfonamide analogs. Chemical Papers 77:12, pages 7903-7918.
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Rania Alaaeldin, Islam M. Abdel-Rahman, Fares E. M. Ali, Amany Abdlrehim Bekhit, Eyad Y. Elhamadany, Qing-Li Zhao, Zheng-Guo Cui & Moustafa Fathy. (2022) Dual Topoisomerase I/II Inhibition-Induced Apoptosis and Necro-Apoptosis in Cancer Cells by a Novel Ciprofloxacin Derivative via RIPK1/RIPK3/MLKL Activation. Molecules 27:22, pages 7993.
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Ahmed K.B.A.W. Farouk, Heba Abdelrasheed Allam, Essam Rashwan, Riham F. George & Safinaz E-S. Abbas. (2022) Design and synthesis of some new 6-bromo-2-(pyridin-3-yl)-4-substituted quinazolines as multi tyrosine kinase inhibitors. Bioorganic Chemistry 128, pages 106099.
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Gheorghe Roman. (2022) Anticancer Activity of Mannich Bases: A Review of Recent Literature. ChemMedChem 17:16.
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Neha V. Bhilare, Vinayak S. Marulkar, Pramodkumar J. Shirote, Shailaja A. Dombe, Vilas J. Pise, Pallavi L. Salve, Shantakumar M. Biradar, Vishal D. Yadav, Prakash D. Jadhav, Anjali A. Bodhe, Smita P. Borkar, Prachi M. Ghadge, Pournima A. Shelar, Apurva V. Jadhav & Kirti C. Godse. (2022) Mannich Bases: Centrality in Cytotoxic Drug Design. Medicinal Chemistry 18:7, pages 735-756.
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Hao-Zhao Wei, Yin Wei & Min Shi. (2021) Intramolecular difunctionalization of methylenecyclopropanes tethered with carboxylic acid by visible-light photoredox catalysis. Organic Chemistry Frontiers 8:16, pages 4527-4532.
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Cem Yamali, Hiroshi Sakagami, Yoshihiro Uesawa, Kota Kurosaki, Keitaro Satoh, Yoshiko Masuda, Satoshi Yokose, Abdulilah Ece, Silvia Bua, Andrea Angeli, Claudiu T. Supuran & Halise Inci Gul. (2021) Comprehensive study on potent and selective carbonic anhydrase inhibitors: Synthesis, bioactivities and molecular modelling studies of 4-(3-(2-arylidenehydrazine-1-carbonyl)-5-(thiophen-2-yl)-1H-pyrazole-1-yl) benzenesulfonamides. European Journal of Medicinal Chemistry 217, pages 113351.
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Cem YAMALI & Halise İnci GÜL. (2021) Cytotoxic effects of Mannich bases via induction of caspase-3 pathway on human oral squamous cell carcinoma. Journal of the Turkish Chemical Society Section A: Chemistry 8:1, pages 187-194.
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Padmini TR, Vagdevi HM, Usha Jinendra & Ravikiran B. (2021) Synthesis of benzoxazole derivatives by Mannich reaction and invitro cytotoxic, antimicrobial and docking studies. Chemical Data Collections 31, pages 100628.
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K. Kucukoglu, H. I. Gul & H. Sakagami. (2020) Evaluation of Cytotoxic Properties of N,N'-bis[(1-aryl-3-heteroaryl)propylidene]-hydrazine dihydrochlorides. Pharmaceutical Chemistry Journal 54:8, pages 784-787.
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Mehtap Tugrak, Halise Inci Gul, Hiroshi Sakagami & Ilhami Gulcin. (2020) Synthesis, cytotoxic, and carbonic anhydrase inhibitory effects of new 2‐(3‐(4‐methoxyphenyl)‐5‐(aryl)‐4,5 ‐dihydro‐1 H ‐pyrazol‐1‐yl)benzo[ d ]thiazole derivatives . Journal of Heterocyclic Chemistry 57:7, pages 2762-2768.
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Sinan Bilginer, Halise I. Gul, Feyza S. Erdal, Hiroshi Sakagami & Ilhami Gulcin. (2020) New halogenated chalcones with cytotoxic and carbonic anhydrase inhibitory properties: 6‐(3‐Halogenated phenyl‐2‐propen‐1‐oyl)‐2(3 H )‐benzoxazolones . Archiv der Pharmazie 353:6, pages 1900384.
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Cem Yamali, Halise Inci Gul, Abdulilah Ece, Silvia Bua, Andrea Angeli, Hiroshi Sakagami, Ertan Sahin & Claudiu T. Supuran. (2019) Synthesis, biological evaluation and in silico modelling studies of 1,3,5-trisubstituted pyrazoles carrying benzenesulfonamide as potential anticancer agents and selective cancer-associated hCA IX isoenzyme inhibitors. Bioorganic Chemistry 92, pages 103222.
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Mehtap Tugrak, Halise Inci Gul, Kenjiro Bandow, Hiroshi Sakagami, Ilhami Gulcin, Yusuf Ozkay & Claudiu T. Supuran. (2019) Synthesis and biological evaluation of some new mono Mannich bases with piperazines as possible anticancer agents and carbonic anhydrase inhibitors. Bioorganic Chemistry 90, pages 103095.
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Halise Inci Gul, Mehtap Tugrak, Mustafa Gul, Sertac Mazlumoglu, Hiroshi Sakagami, Ilhami Gulcin & Claudiu T. Supuran. (2019) New phenolic Mannich bases with piperazines and their bioactivities. Bioorganic Chemistry 90, pages 103057.
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Kaan Kucukoglu, Halise Inci Gul, Parham Taslimi, Ilhami Gulcin & Claudiu T. Supuran. (2019) Investigation of inhibitory properties of some hydrazone compounds on hCA I, hCA II and AChE enzymes. Bioorganic Chemistry 86, pages 316-321.
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Dilan Ozmen Ozgun, Halise Inci Gul, Cem Yamali, Hiroshi Sakagami, Ilhami Gulcin, Murat Sukuroglu & Claudiu T. Supuran. (2019) Synthesis and bioactivities of pyrazoline benzensulfonamides as carbonic anhydrase and acetylcholinesterase inhibitors with low cytotoxicity. Bioorganic Chemistry 84, pages 511-517.
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Mehtap Tugrak, Halise Inci Gul, Hiroshi Sakagami, Ilhami Gulcin & Claudiu T. Supuran. (2018) New azafluorenones with cytotoxic and carbonic anhydrase inhibitory properties: 2-Aryl-4-(4-hydroxyphenyl)-5H-indeno[1,2-b]pyridin-5-ones. Bioorganic Chemistry 81, pages 433-439.
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Halise Inci Gul, Cem Yamali, Gulsen Gunesacar, Hiroshi Sakagami, Noriyuki Okudaira, Yoshihiro Uesawa & Hajime Kagaya. (2018) Cytotoxicity, apoptosis, and QSAR studies of phenothiazine derived methoxylated chalcones as anticancer drug candidates. Medicinal Chemistry Research 27:10, pages 2366-2378.
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Kaan Kucukoglu, Mustafa Gul, Halise Inci Gul, Rengul Cetin-Atalay & Bernard Geny. (2018) Cytotoxicities of novel hydrazone compounds with pyrrolidine moiety: inhibition of mitochondrial respiration may be a possible mechanism of action for the cytotoxicity of new hydrazones. Medicinal Chemistry Research 27:9, pages 2116-2124.
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T. Kim-Dung Hoang, T. Kim-Chi Huynh, T. Hong-Tuoi Do & Thanh-Danh Nguyen. (2018) Mannich aminomethylation of flavonoids and anti-proliferative activity against breast cancer cell. Chemical Papers 72:6, pages 1399-1406.
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Cem Yamali, Halise Inci Gul, Abdulilah Ece, Parham Taslimi & Ilhami Gulcin. (2018) Synthesis, molecular modeling, and biological evaluation of 4-[5-aryl-3-(thiophen-2-yl)-4,5-dihydro-1 H -pyrazol-1-yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes . Chemical Biology & Drug Design 91:4, pages 854-866.
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Ghaneya S Hassan, Hanan H Georgey, Riham F George & Eman R Mohammed. (2018) Construction of some cytotoxic agents with aurone and furoaurone scaffolds. Future Medicinal Chemistry 10:1, pages 27-52.
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Cem Yamali, Dilan Ozmen Ozgun, Halise Inci Gul, Hiroshi Sakagami, Cavit Kazaz & Noriyuki Okudaira. (2017) Synthesis and structure elucidation of 1-(2,5/3,5-difluorophenyl)-3-(2,3/2,4/2,5/3,4-dimethoxyphenyl)-2-propen-1-ones as anticancer agents. Medicinal Chemistry Research 26:9, pages 2015-2023.
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Mehtap Tugrak, Halise Inci Gul, Hiroshi Sakagami & Ebru Mete. (2017) Synthesis and anticancer properties of mono Mannich bases containing vanillin moiety. Medicinal Chemistry Research 26:7, pages 1528-1534.
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Mehtap Tugrak, Abdullah Aydin, Halise Inci Gul, Ertan Sahin & Mehmet Akkurt. (2017) Crystal structure of ( E )-2-({4-hydroxy-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]phenyl} methylidene)-1-indanone, C 23 H 26 N 2 O 3 . Zeitschrift für Kristallographie - New Crystal Structures 232:1, pages 113-115.
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