Maddineni Aruna Kumari, Chunduri Venkatarao
Maddineni Aruna Kumari1*, Chunduri Venkatarao2
1Department of Chemistry, Dr. APJ Abdulkalam IIIT Ongole, RGUKT, Andhra Pradesh, India.
2Department of Chemistry, Sri Venkateswara University, Tirupati 517502, Andhra Pradesh, India.
Volume - 13,
Issue - 5,
Year - 2020
Pyrazole is a five-membered heterocyclic compound containing two nitrogen atoms in adjacent position. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. Owing to this diversity in the biological field, this nucleus has attracted the attention of many researchers to study its skeleton chemically and biologically. There is an increase in the interest of analyzing different biological properties pyrazole derivatives. In this review we have collated, the recent developments in the biological activities of different pyrazole derivatives.
Cite this article:
Maddineni Aruna Kumari, Chunduri Venkatarao. A Review on Recent Trends in the Bioactive Studies of Pyrazole Derivatives. Asian J. Research Chem. 2020; 13(5):383-394. doi: 10.5958/0974-4150.2020.00072.3
Maddineni Aruna Kumari, Chunduri Venkatarao. A Review on Recent Trends in the Bioactive Studies of Pyrazole Derivatives. Asian J. Research Chem. 2020; 13(5):383-394. doi: 10.5958/0974-4150.2020.00072.3 Available on: https://ajrconline.org/AbstractView.aspx?PID=2020-13-5-14
1. Srivastava M, Singh J, Singh SB, Tiwari K, Pathak KV and Singh J. Synthesis of novel fused heterocycleoxa-aza-phenanthrene and anthracene derivatives via sequential one-pot synthesis in aqueous micellar system. Green Chemistry. 2012; 14: 901.
2. Pai G and Chattopadhyay AP. N-arylation of nitrogen containing heterocycles with aryl halides using copper nanoparticle catalytic system. Tetrahedron Letters. 2016; 57: 3140.
3. Bekhit AA, Hassan AM, Abd El Razik HA, El-Miligy MM, El-Agroudy EJ and Bekhit AD. New heterocyclic hybrids of pyrazole and its bioisosteres: Design, synthesis and biological evaluation as dual acting antimalarial-antileishmanial agents. Europian Journal of Medicinal Chemistry. 2015; 94: 30.
4. Sony JK and Ganguly S. A battle against AIDS: New pyrazole key to an older lock-reverse transcriptase. International Journal of Phamacy and Pharmaceutical Sciences. 2016; 8: 75.
5. Robin EM, David RG, Vijayalekshmi S. An antibacterial pyrazole derivative from Burkholderia glumae, a bacterial pathogen of rice. Phytochemistry. 2008; 69: 2704-2707.
6. Xia Y, Fan C, Zhao BX, Zhao J, Shin DS, Miao JY. Synthesis and structure–activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells. Europian Journal of Medicinal Chemistry. 2008; 43: 2347-2353.
7. Bandgar BP, Totre JV, Gawande SS, Khobragade CN, Warangkar SC, Kadam PD. Synthesis of novel 3,5-diaryl pyrazole derivatives using combinatorial chemistry as inhibitors of tyrosinase as well as potent anticancer, anti-inflammatory agents. Bioorganic and Medicinal Chemistry. 2010; 18(16): 6149-6155.
8. Karthikeyan MS, Holla BS, Kumari NS. Synthesis and antimicrobial studies on novel chloro-fluorine containing hydroxy pyrazolines. Europian Journal of Medicinal Chemistry. 2007; 42: 30-36.
9. Kees KL, Fitzgerald JJ, Steiner KE, Mattes, Mihan B, Tosi T, Mondoro D and McCalebML. New potent antihyperglycemic agents in db/db mice: synthesis and structure-activity relationship studies of (4-substituted benzyl) (trifluoromethyl)pyrazoles and –pyrazolones. Journal of Medicinal Chemistry. 1996; 39: 3920.
10. Bailey DM, Hansen PE, Hlavac AG, Baizman ER, Pearl J, Defelice AF and Feigenson ME. 3,4- Diphenyl-1H-pyrazole-1-propanamine antidepressants. Journal of Medicinal Chemistry. 1985; 28: 256.
11. Michon V, Penhoat CHD, Tombret F, Gillardin JM, Lepage F and Berthon L. Preparation, structural analysis and anticonvulsant activity of 3- and 5-aminopyrazole N-benzoyl derivatives. European Journal of Medicinal Chemistry. 1995; 30: 147.
12. Jamwal A, Javed A and Bhardwaj V. A review on pyrazole derivatives of pharmacological potential. Journal of Pharmacy and Biosciences. 2013; 3: 114.
13. Heller ST and Natarajan SR. 1,3-Diketones from Acid Chlorides and Ketones : A Rapid and General One- Pot Synthesis of Pyrazoles. Organic Letters. 2006; 8: 2675.
14. Knorr L, Synthese von Pyrrolderivaten. Berichte der Deutschen Chemischen Gesellschaft. 1884; 17: 2032.
15. Aggarwal VK, Vicente JD, Bonnert RVJ. A Novel One-Pot Method for the Preparation of Pyrazoles by 1,3-Dipolar Cycloadditions of Diazo Compounds Generated in Situ. Organic Chemistry. 2003; 68: 5381.
16. Katritzky AR, Wang M, Zhang S, Voronkov MV. Regioselective Synthesis of Polysubstituted Pyrazoles and Isoxazoles. Journal of Organic Chemistry. 2001; 66: 6787.
17. Nisheeth CD, Hitesh MS, Ghanshyam MK, Hasit VV. Synthesis and Antibacterial and Cytotoxic Activities of New N‐3 Substituted Thiazolidine‐2,4‐dione Derivatives Bearing the Pyrazole Moiety. Archive der Pharmazie – Chemistry in Life Sciences. 2014; 347: 1–10.
18. Fan JM, Tao S, Wen ZD, Ming HL, Zhong ZT. Discovery of Novel Pyrazole Derivatives as Potent Neuraminidase Inhibitors against Influenza H1N1 Virus. Archive der Pharmazie – Chemistry in Life Sciences. 2016; 349: 168–174.
19. Hashem AA, Gouda MA. Synthesis and Antimicrobial Activity of Some Novel Quinoline, Chromene, Pyrazole Derivatives Bearing Triazolopyrimidine Moiety. Journal of Heterocyclic Chemistry. 2017; 54 (2): 850-858.
20. Manjunath G, Mahesh M, Bheemaraju G, Venkata RP. Synthesis of New Pyrazole Derivatives Containing Quinoline Moiety via Chalcones: A Novel Class of Potential Antibacterial and Antifungal Agents. Chemical Science Transactions. 2016; 5(1): 61-74.
21. Poonam Y, Nalini VP. Synthesis and evaluation of some bioactive compounds having oxygen and nitrogen heteroatom. Journal of Chemical Sciences. 2013; 125(1): 165–173.
22. Jacob KS, Ganguly S. Synthesis, anti microbial screening and cytotoxic studies of some novel pyrazole analogs. Journal of Applied Pharmaceutical Science. 2016; 6 (11):135-141.
23. Prasanna AD, Sonali RJ. Design and Synthesis of Pyrazole-3-one Derivatives as Hypoglycaemic Agents. International Journal of Medicinal Chemistry. 2015; Article ID 670181.
24. Wang DJ, Hua L, Yan FK, Yan JH, Xian HW. Synthesis and anti-microbial activities of 1,3,5-trisubstituted-pyrazole derivatives containing a pyridyl moiety. Journal of Chilean Chemical Society, 2015; 60 (1): 2857-2860.
25. Reddy R, Kumar PP, Rao JV, Subbarao J. Synthesis, characterization and biological evaluation of certain new pyrazole derivatives. International Journal of Chemical Sciences. 2015; 13(3): 1383-1392.
26. Sthalam VK, Bethanamudi P, Gadidasu KK, Kumar TR, Velidandi A. Synthesis, in vitro antibacterial activity and docking studies of newer pyrazole derivatives. Pharmacophore. 2015; 6 (4): 196-204.
27. Kendre BV, Landge MG, Bhusare SR. Synthesis and biological evaluation of some novel pyrazole, isoxazole, benzoxazepine, benzothiazepine and benzodiazepine derivatives bearing an aryl sulfonate moiety as antimicrobial and anti-inflammatory agents. Arabian Journal of Chemistry. 2019; 12 (8): 2091-2097.
28. Miniyar PB, Barmade MA, Mahajan AA. Synthesis and biological evaluation of 1-(5-(2-chloroquinolin-3-yl)-3-phenyl-1H-pyrazol-1-yl)ethanone derivatives as potential antimicrobial agents. J. Saudi Chemical Society. 2015; 19 (6): 655–660.
29. Mu JX, Shi YX, Yang MY, Sun ZH, Liu XH, Li BJ, Sun NB. Design, Synthesis, DFT Study and Antifungal Activity of Pyrazolecarboxamide Derivatives. Molecules. 2016; 21: 68–78.
30. Thore SN, Gupta SV, Baheti KG. Novel ethyl-5-amino-3-methylthio-1H-pyrazole-4-carboxylates: Synthesis and pharmacological activity. Journal of Saudi Chemical Sciences. 2016; 20 (3): 259–264.
31. Nayak N, Ramprasad J, Dalimba U. Synthesis and antitubercular and antibacterial activity of some active fluorine containing quinoline–pyrazole hybrid derivatives. Jornal of Fluorine Chemistry. 2016; 183: 59–68.
32. Ravula P, Vamaraju HB, Paturi M, Chandra JNGNS, Design, synthesis, in silico and antiproliferative evaluation of novel pyrazole derivatives as VEGFR‐2 inhibitors. Archive der Pharmazie – Chemistry in Life Sciences. 2018; 351(1): 1700234.
33. Mohamed FES, Mostafa MG, Samir YA, Eman AF, Said AS, Yousry AA. Quinoline derivatives bearing pyrazole moiety: Synthesis and biological evaluation as possible antibacterial and antifungal agents. European Journal of Medicinal Chemistry. 2018; 143: 1463-1473.
34. Bhatt BH, Sharma S. Synthesis and antimicrobial activity of pyrazole nucleus containing 2-thioxothiazolidin-4-one derivatives. Arabian Journal of Chemistry. 2017; 10: S1590–S1596.
35. Amaroju S, Kalaga MN, Srinivasarao S, Napiorkowska A, Augustynowicz KE, Murugesan S, Chander S, Krishnan R, Sekhar CKVG. Identification and development of pyrazolo[4,3-c]pyridine carboxamides as Mycobacterium tuberculosis pantothenate synthetase inhibitors. New Journal of Chemistry. 2017; 41: 347–357.
36. Nayak N, Ramprasad J, Dalimba U. Design, Synthesis, and Biological Evaluation of New 8‐Trifluoromethylquinoline Containing Pyrazole‐3‐carboxamide Derivatives. Journal of Heterocyclic Chemistry. 2017; 54: 171–182.
37. Kenchappa R, Bodke YD, Chandrashekar A, Sindhe MA, Peethambar SK. Synthesis of coumarin derivatives containing pyrazole and indenone rings as potent antioxidant and antihyperglycemic agents. Arabian Journal of Chemistry. 2017; 10 (2): S3895–S3906.
38. Turkan F, Cetin A, Taslimi P, Gulçin İ. Archive der Pharmazie – Chemistry in Life Sciences. 2018; 1–7.
39. Marwa FH, Sabour R. Design, synthesis and biological evaluation of novel 1,3,4-trisubstituted pyrazole derivatives as potential chemotherapeutic agents for hepatocellular carcinoma. Bioorganic Chemistry. 2018; 78: 149–157.
40. Akhtar MdJ, Khan AA, Ali Z, Dewangan RP, Rafi Md, Hassan QMd, Akhtar SMd, Siddiqui AA, Partap S, Pasha S, Yar MS. Synthesis of stable benzimidazole derivatives bearing pyrazole as anticancer and EGFR receptor inhibitors. Bioorganic Chemistry. 2018; 78: 158–169.
41. Verma G, Chashoo G, Ali A, Khan MF, Akhtar W, Ali I, Akhtar M, Alam MM, Shaquiquzzaman M. Synthesis of pyrazole acrylic acid based oxadiazole and amide derivatives as antimalarial and anticancer agents. Bioorganic Chemistry. 2018; 77: 106–124.
42. Cui CY, Liu J, Zheng HB, Jin XY, Zhao XY, Chang WQ, Sun B, Lou HX. Diversity-oriented synthesis of pyrazoles derivatives from flavones and isoflavones leads to the discovery of promising reversal agents of fluconazole resistance in Candida albicans. Bioorganic & Medicinal Chemistry Letters. 2018; 28 (9): 1545–1549.
43. Liu H, Ren ZL, Wang W, Gong JX, Chu MJ, Ma QW, Wang JC, Lv XH. Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity. European Journal of Medicinal Chemistry. 2018; 157: 81-87.
44. Dai H, Ge S, Guo J, Chen S, Huang M, Yang J, Sun S, Shi Y, Ling Y. Development of novel bis-pyrazole derivatives as antitumor agents with potent apoptosis induction effects and DNA damage. European Journal of Medicinal Chemistry. 2018; 143: 1066-1076.
45. Channar PA, Afzal S, Ejaz SA, Saeed A, Larik FA, Mahesar PA, Lecka J, Sévigny J, Erben MF, Iqbal J. Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile. European Journal of Medicinal Chemistry. 2018; 156: 461-478.
46. Jadhav SB, Fatema S, Sanap G, Farooqui M. Antitubercular Activity and Synergistic Study of Novel Pyrazole Derivatives. Journal of Heterocyclic Chemistry. 2018; 55 (7): 1634-1644.
47. Sayed GH, Azab ME, Anwer KE, Raouf MA, Negm NA. Pyrazole, pyrazolone and enaminonitrile pyrazole derivatives: Synthesis, characterization and potential in corrosion inhibition and antimicrobial applications. Journal of Molecular Liquids. 2018; 252: 329-338.
48. Milind VG, Rahul DK, Shrikant VH, Kadam SN, Ajay NA, Bhaskar SD. Synthesis of Pyrazolo [4,3-e] Pyrimido [1,2-a] Pyrimidin-3-Amine Derivatives and their Antimicrobial Activity. Journal of Pharmaceutical, Chemical and Biological Sciences. 2018; 5(4): 376-385.
49. Mahesh B, Belagali SL. Synthesis, characterization and biological screening of pyrazole-conjugated benzothiazole analogs. Future Medicinal Chemistry. 2018; 10 (1): 71-87.
50. Sunil K, Rajat K. Synthesis and Antimicrobial Activity of 5-(Substituted-Phenyl)-3-(Furan-2- Yl)-4,5-Dihydro-1H-Pyrazole Compounds Using Silver Trifluro Methane Sulphonate as Catalyst. Der Pharmacia Lettre. 2018; 10 (8): 57-67.
51. Khumar SAB, Ezhilarasi MR, Prabha B. Molecular Docking Study of Novel Synthesized Pyrazole Derivatives and their Antibacterial Activity. Asian Journal of Chemistry. 2018; 30 (4): 741-746.
52. Zhou S, Xu L, Cao M. Anticancer properties of novel pyrazole‐containing biguanide derivatives with activating the adenosine monophosphate‐activated protein kinase signaling pathway. Archive der Pharmazie – Chemistry in Life Sciences. 2019; 352 (9): 1900075.
53. Abdellatif KRA, Abdelall EKA, Lamie PF, Labib MB, Nahaas ESE, Abdelhakeem MM. New pyrazole derivatives possessing amino/methanesulphonyl pharmacophore with good gastric safety profile: Design, synthesis, cyclooxygenase inhibition, anti-inflammatory activity and histopathological studies. Bioorganic Chemistry. 2020; 95: 103540.
54. Khaled RAA, Wael AAF, Mostafa YA, Zaher DM, Omar HA. Thiohydantoin derivatives incorporating a pyrazole core: Design, synthesis and biological evaluation as dual inhibitors of topoisomerase-I and cycloxygenase-2 with anti-cancer and anti-inflammatory activities. Bioorganic Chemistry. 2019; 91: 103132.
55. Murahari M, Mahajan V, Neeladri S, Kumar MS, Mayur YC. Thiohydantoin derivatives incorporating a pyrazole core: Design, synthesis and biological evaluation as dual inhibitors of topoisomerase-I and cycloxygenase-2 with anti-cancer and anti-inflammatory activities. Bioorganic Chemistry. 2019; 86: 583-597.
56. Dina MO, Ghaly MA, Messery SME, Farid AB, Latif EA, Ihsan AS. Targeting hepatocellular carcinoma: Synthesis of new pyrazole-based derivatives, biological evaluation, DNA binding, and molecular modeling studies. Bioorganic Chemistry. 2019; 88: 102917.
57. Taslimi P, Türkan F, Cetin A, Burhan H, Karamane M, Bildirici I, İlhami G, Şen F. Pyrazole[3,4-d]pyridazine derivatives: Molecular docking and explore of acetylcholinesterase and carbonic anhydrase enzymes inhibitors as anticholinergics potentials. Bioorganic Chemistry. 2019; 92: 103213.
58. Turkan F, Cetin A, Taslimi P, Karaman M, İlhami G. Synthesis, biological evaluation and molecular docking of novel pyrazole derivatives as potent carbonic anhydrase and acetylcholinesterase inhibitors. Bioorganic Chemistry. 2019; 86: 420–427.
59. Ran F, Liu Y, Zhang D, Liu M, Zhao G. Discovery of novel pyrazole derivatives as potential anticancer agents in MCL. Bioorganic & Medicinal Chemistry Letters. 2019; 29 (9): 1060–1064.
60. Sun L, Wang P, Xu L, Gao L, Li J, Piao H. Discovery of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups as potential PTP1B inhibitors. Bioorganic & Medicinal Chemistry Letters. 2019; 29 (10): 1187–1193.
61. Takate SJ, Shinde AD, Karale BK, Akolkar H, Nawale L, Sarkar D, Mhaske PC. Thiazolyl-pyrazole derivatives as potential antimycobacterial agents. Bioorganic & Medicinal Chemistry Letters. 2019; 29 (10): 1199–1202.
62. Zhang TY, Zheng CJ, Wu J, Sun LP, Piao HR. Synthesis of novel dihydrotriazine derivatives bearing 1,3-diaryl pyrazole moieties as potential antibacterial agents. Bioorganic & Medicinal Chemistry Letters. 2019; 29 (9): 1079-1084.
63. Zhan W, Che J, Xu L, Wu Y, Hu X, Zhou Y, Cheng G, Hu Y, Dong X, Li J. Discovery of pyrazole-thiophene derivatives as highly Potent, orally active Akt inhibitors. European Journal of Medicinal Chemistry. 2019; 180: 72-85.
64. Romagnoli R, Oliva P, Salvador KM, Camacho ME, Padroni C, Brancale A, Ferla S, Hamel E, Ronca R, Grillo E, Bortolozzi R, Rruga F, Mariotto E, Viola G. Design, synthesis and biological evaluation of novel vicinal diaryl-substituted 1H-Pyrazole analogues of combretastatin A-4 as highly potent tubulin polymerization inhibitors. European Journal of Medicinal Chemistry. 2019; 181: 111577.
65. Monteiro ME, Lechuga G, Lara LS, Souto BA, Vigan_o MG, Bourguignon SC, Calvet CM, Oliveira Jr. FOR, Alves CR, S Silva F, Santos MS, Pereira MCS. Synthesis, structure-activity relationship and trypanocidal activity of pyrazole-imidazoline and new pyrazole-tetrahydropyrimidine hybrids as promising chemotherapeutic agents for Chagas disease. European Journal of Medicinal Chemistry. 2019; 182: 111610.
66. Hassan GS, Rahman ADE, Abdelmajeed EA, Refaey RH, Salem AM, Nissan YM. Synthesis, structure-activity relationship and trypanocidal activity of pyrazole-imidazoline and new pyrazole-tetrahydropyrimidine hybrids as promising chemotherapeutic agents for Chagas disease. European Journal of Medicinal Chemistry. 2019; 171: 332-342.
67. Li Q, Zhi WZ, Peng PC, Cheng XT, Jian QW, Liang H, Xing HL, Yong GZ. Synthesis, Crystal Structure, Antifungal Activity, and Docking Study of Difluoromethyl Pyrazole Derivatives. Journal of Heterocyclic Chemistry. 2019; 56 (9): 2536-2541.
68. Bhatt JJ, Suresh KD, Mrugesh HT. Synthesis, characterization and anti-microbial activity of pyrazole capped 2-azitidinone derivatives. RJLBPCS. 2019; 5(1): 647-662.
69. Jordan AMcK, Reham FB, Azhaar TA, Omkar K, Kalun B, Frederic M, Edward GN, Andis K. Synthesis and Evaluation of Novel Pyrazole Ethandiamide Compounds as Inhibitors of Human THP-1 Monocytic Cell Neurotoxicity. Cells. 2019; 8 (7): 655-666.