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Medicinal Chemistry

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ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

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Mini-Review Article

Pyrazole Containing Anti-HIV Agents: An Update

Author(s): Sanjay Kumar*, Shiv Gupta*, Varsha Rani and Priyanka Sharma

Volume 18, Issue 8, 2022

Published on: 06 April, 2022

Page: [831 - 846] Pages: 16

DOI: 10.2174/1573406418666220106163846

Price: $65

Abstract

Background: Pyrazole scaffolds have gained importance in drug discovery and development for various pharmacological activities like antiviral, antifungal, anticancer, antidepressant, antiinflammatory, antibacterial, etc. Additionally, the pyrazole moiety has shown potent anti-HIV activity as a core heterocycle or substituted heterocycles derivatives (mono, di, tri, tetra, and fused pyrazole derivatives). To assist the development of further potential anti-HIV agents containing pyrazole nucleus, here we have summarized pyrazole containing anti-HIV compounds that have been reported by researchers all over the world for the last two decades.

Objective: The present review concentrates on an assortment of pyrazole containing compounds, particularly for potential therapeutic activity against HIV.

Methods: Google Scholar, Pubmed, and SciFinder were searched databases with ‘‘pyrazol’’ keywords. Further, the year of publication and keywords ‘‘Anti-HIV’’ filter was applied to obtain relevant reported literature for anti-HIV agents containing pyrazole as a core or substituted derivatives.

Results: This review article has shown the comprehensive compilation of 220 compounds containing pyrazole nucleus and possessing anti-HIV activity by sorting approximately 40 research articles from 2001 to date. 1-(4-Benzoylpiperazin-1-yl)-2-(4-fluoro-7-(1H-pyrazol-3-yl)-1H-pyrrolo[2,3-c]pyridin- 3-yl)ethane-1,2-dione (13), 3-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-fluoro-1H-pyrrolo[2,3- c]pyridin-7-yl)-1H-pyrazole-5-carboxamide (31), 3-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4- fluoro-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-pyrazole-5-carboxamide (88), 3-cyanophenoxypyrazole derivative (130), and 4-(4-chlorophenyl)-5-(4-methyl-5-((4-nitrophenyl)diazenyl)thiazol-2-yl)-3- phenyl-5,6-dihydro-4H-pyrazolo[4,3-d]isoxazole (178) were the most potent mono-, di-, tri-, tetrasubstituted, and fused pyrazole derivatives, respectively, which have shown potent anti-HIV activity among all the described derivatives as compared with standard anti-HIV drugs.

Conclusion: This review article provides an overview of the potential therapeutic activity of pyrazole derivatives against HIV that will be helpful for designing pyrazole containing compounds for anti-HIV activity.

Keywords: Pyrazole, anti-HIV, AIDS, fused-pyrazole, pyrazolo, pyrazoline.

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Graphical Abstract

[1]
WHO. Available from: https://www.who.int/news-room/fact-sheets/detail/hiv-aids (Accessed on May 26, 2021).
[2]
Davies, D.T. Aromatic Heterocyclic Chemistry; Oxford Uni-versity Press: Oxford, United Kingdom, 1992.
[3]
Yang, Z.; Li, P.; Gan, X. Novel pyrazole-hydrazone deriva-tives containing an isoxazole moiety: Design, synthesis, and antiviral activity. Molecules, 2018, 23(7), 1798.
[http://dx.doi.org/10.3390/molecules23071798] [PMID: 30037021]
[4]
Chougala, B.M.; Samundeeswari, S.; Holiyachi, M.; Shastri, L.A.; Dodamani, S.; Jalalpure, S.; Dixit, S.R.; Joshi, S.D.; Sunagar, V.A. Synthesis, characterization and molecular docking studies of substituted 4-coumarinylpyrano[2,3-c]pyrazole derivatives as potent antibacterial and anti-inflammatory agents. Eur. J. Med. Chem., 2017, 125, 101-116.
[http://dx.doi.org/10.1016/j.ejmech.2016.09.021] [PMID: 27657808]
[5]
El Shehry, M.F.; Ghorab, M.M.; Abbas, S.Y.; Fayed, E.A.; Shedid, S.A.; Ammar, Y.A. Quinoline derivatives bearing py-razole moiety: Synthesis and biological evaluation as possible antibacterial and antifungal agents. Eur. J. Med. Chem., 2018, 143, 1463-1473.
[http://dx.doi.org/10.1016/j.ejmech.2017.10.046] [PMID: 29113746]
[6]
Bennani, F.E.; Doudach, L.; Cherrah, Y.; Ramli, Y.; Karrou-chi, K.; Ansar, M.; Faouzi, M.E.A. Overview of recent devel-opments of pyrazole derivatives as an anticancer agent in dif-ferent cell line. Bioorg. Chem., 2020, 97, 103470.
[http://dx.doi.org/10.1016/j.bioorg.2019.103470] [PMID: 32120072]
[7]
Cheng, C.C.; Elslager, E.F.; Werbel, L.M.; Priebe, S.R.; Leo-pold, W.R. III Pyrazole derivatives. 5. Synthesis and antineoplastic activity of 3-(2-chloroethyl)-3,4-dihydro-4-oxopyrazolo[5,1-d]-1,2,3, 5-tetrazine-8-carboxamide and re-lated compounds. J. Med. Chem., 1986, 29(8), 1544-1547.
[http://dx.doi.org/10.1021/jm00158a041] [PMID: 3735323]
[8]
Abdel-Aziz, M.; Abuo-Rahma, G-D.; Hassan, A.A. Synthesis of novel pyrazole derivatives and evaluation of their antide-pressant and anticonvulsant activities. Eur. J. Med. Chem., 2009, 44(9), 3480-3487.
[http://dx.doi.org/10.1016/j.ejmech.2009.01.032] [PMID: 19268406]
[9]
Bekhit, A.A.; Abdel-Aziem, T. Design, synthesis and biologi-cal evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents. Bioorg. Med. Chem., 2004, 12(8), 1935-1945.
[http://dx.doi.org/10.1016/j.bmc.2004.01.037] [PMID: 15051061]
[10]
Kumar, P.; Chandak, N.; Kaushik, P.; Sharma, C.; Kaushik, D.; Aneja, K.R.; Sharma, P.K. Synthesis and biological eval-uation of some pyrazole derivatives as anti-inflammatory–antibacterial agents. Med. Chem. Res., 2012, 21, 3396-3405.
[http://dx.doi.org/10.1007/s00044-011-9853-4]
[11]
Silva, V.L.M.; Elguero, J.; Silva, A.M.S. Current progress on antioxidants incorporating the pyrazole core. Eur. J. Med. Chem., 2018, 156, 394-429.
[http://dx.doi.org/10.1016/j.ejmech.2018.07.007] [PMID: 30015075]
[12]
Abdellatif, K.R.A.; Fadaly, W.A.A.; Kamel, G.M.; Elshaier, Y.A.M.M.; El-Magd, M.A. Design, synthesis, modeling stud-ies and biological evaluation of thiazolidine derivatives con-taining pyrazole core as potential anti-diabetic PPAR-& ago-nists and anti-inflammatory COX-2 selective inhibitors. Bioorg. Chem., 2019, 82, 86-99.
[http://dx.doi.org/10.1016/j.bioorg.2018.09.034] [PMID: 30278282]
[13]
Keri, R.S.; Chand, K.; Ramakrishnappa, T.; Nagaraja, B.M. Recent progress on pyrazole scaffold-based antimycobacterial agents. Arch. Pharm. (Weinheim), 2015, 348(5), 299-314.
[http://dx.doi.org/10.1002/ardp.201400452] [PMID: 25820461]
[14]
Jadhav, S.B.; Fatema, S.; Sanap, G.; Farooqui, M. Antituber-cular activity and synergistic study of novel pyrazole deriva-tives. J. Heterocycl. Chem., 2018, 55, 1634-1644.
[http://dx.doi.org/10.1002/jhet.3198]
[15]
Ouyang, G.; Cai, X.J.; Chen, Z.; Song, B.A.; Bhadury, P.S.; Yang, S.; Jin, L.H.; Xue, W.; Hu, D.Y.; Zeng, S. Synthesis and antiviral activities of pyrazole derivatives containing an oxime moiety. J. Agric. Food Chem., 2008, 56(21), 10160-10167.
[http://dx.doi.org/10.1021/jf802489e] [PMID: 18939848]
[16]
Gao, M.; Qu, K.; Zhang, W.; Wang, X. Pharmacological activi-ty of pyrazole derivatives as an anticonvulsant for benefit against epilepsy. Neuroimmunomodulation, 2021, 28(2), 90-98.
[http://dx.doi.org/10.1159/000513297] [PMID: 33774633]
[17]
Building the foundation for better health outcomes. Available from: https://www.drugbank.ca/ (Accessed on May 28, 2021).
[18]
Haas, H. History of antipyretic analgesic therapy. Am. J. Med., 1983, 75(5A), 1-3.
[http://dx.doi.org/10.1016/0002-9343(83)90225-5] [PMID: 6359858]
[19]
Abadi, A.H.; Eissa, A.A.H.; Hassan, G.S. Synthesis of novel 1,3,4-trisubstituted pyrazole derivatives and their evaluation as antitumor and antiangiogenic agents. Chem. Pharm. Bull. (Tokyo), 2003, 51(7), 838-844.
[http://dx.doi.org/10.1248/cpb.51.838] [PMID: 12843591]
[20]
Flower, R.J. The development of COX2 inhibitors. Nat. Rev. Drug Discov., 2003, 2(3), 179-191.
[http://dx.doi.org/10.1038/nrd1034] [PMID: 12612644]
[21]
U. S. Food & Drug Administration. Available from: https://www.fda.gov/drugs/informationon-drugs/approveddrugs/ucm548487.htm (Accessed on May 30, 2021).
[22]
U. S. Food & Drug Administration. Available from: https://www.fda.gov/newsevents/newsroom/-pressannouncements/ucm557102.htm (Accessed on June 1, 2021).
[23]
U. S. Food & Drug Administration. Available from: https://www.fda.gov/Drugs/informationon-drugs (Accessed on June 2, 2021).
[24]
Zhan, P.; Pannecouque, C.; De Clercq, E.; Liu, X. Anti-HIV drug discovery and development: Current innovations and fu-ture trends: miniperspective. J. Med. Chem., 2016, 59(7), 2849-2878.
[http://dx.doi.org/10.1021/acs.jmedchem.5b00497] [PMID: 26509831]
[25]
Liu, Q.; Che, D.; Huang, Q.; Cao, Z.; Zhu, R. Multi-target QSAR study in the analysis and design of HIV-1 inhibitors. Chin. J. Chem., 2010, 28, 1587-1592.
[http://dx.doi.org/10.1002/cjoc.201090269]
[26]
Genin, M.J.; Biles, C.; Keiser, B.J.; Poppe, S.M.; Swaney, S.M.; Tarpley, W.G.; Yagi, Y.; Romero, D.L. Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: Lead identification and SAR of 3- and 4-substituted derivatives. J. Med. Chem., 2000, 43(5), 1034-1040.
[http://dx.doi.org/10.1021/jm990383f] [PMID: 10715167]
[27]
Regueiro-Ren, A.; Xue, Q.M.; Swidorski, J.J.; Gong, Y-F.; Mathew, M.; Parker, D.D.; Yang, Z.; Eggers, B.; D’Arienzo, C.; Sun, Y.; Malinowski, J.; Gao, Q.; Wu, D.; Langley, D.R.; Colonno, R.J.; Chien, C.; Grasela, D.M.; Zheng, M.; Lin, P.F.; Meanwell, N.A.; Kadow, J.F. Inhibitors of human immunode-ficiency virus type 1 (HIV-1) attachment. 12. Structure-activity relationships associated with 4-fluoro-6-azaindole de-rivatives leading to the identification of 1-(4-benzoylpiperazin-1-yl)-2-(4-fluoro-7-[1,2,3]triazol-1-yl-1h-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione (BMS-585248). J. Med. Chem., 2013, 56(4), 1656-1669.
[http://dx.doi.org/10.1021/jm3016377] [PMID: 23360431]
[28]
Seto, M.; Aikawa, K.; Miyamoto, N.; Aramaki, Y.; Kanzaki, N.; Takashima, K.; Kuze, Y.; Iizawa, Y.; Baba, M.; Shiraishi, M. Highly potent and orally active CCR5 antagonists as anti-HIV-1 agents: Synthesis and biological activities of 1-benzazocine derivatives containing a sulfoxide moiety. J. Med. Chem., 2006, 49(6), 2037-2048.
[http://dx.doi.org/10.1021/jm0509703] [PMID: 16539392]
[29]
Karrouchi, K.; Radi, S.; Ramli, Y.; Taoufik, J.; Mabkhot, Y.N.; Al-Aizari, F.A.; Ansar, M. Synthesis and pharmacologi-cal activities of pyrazole derivatives: a review. Molecules, 2018, 23(1), 134.
[http://dx.doi.org/10.3390/molecules23010134] [PMID: 29329257]
[30]
Dwivedi, J.; Sharma, S.; Jain, S.; Singh, A. The synthetic and biological attributes of pyrazole derivatives: A review. Mini Rev. Med. Chem., 2018, 18(11), 918-947.
[http://dx.doi.org/10.2174/1389557517666170927160919] [PMID: 28971774]
[31]
Ganguly, S.; Jacob, S.K. Therapeutic outlook of pyrazole analogs: a mini review. Mini Rev. Med. Chem., 2017, 17(11), 959-983.
[http://dx.doi.org/10.2174/1389557516666151120115302] [PMID: 26586126]
[32]
Bansal, A. A brief review on antimicrobial potential of pyra-zoles (From 2010-2018). Mini Rev. Org. Chem., 2020, 17, 197-222.
[http://dx.doi.org/10.2174/1570193X16666190122162920]
[33]
Khan, M.F.; Alam, M.M.; Verma, G.; Akhtar, W.; Akhter, M.; Shaquiquzzaman, M. The therapeutic voyage of pyrazole and its analogs: A review. Eur. J. Med. Chem., 2016, 120, 170-201.
[http://dx.doi.org/10.1016/j.ejmech.2016.04.077] [PMID: 27191614]
[34]
Jamwal, A.; Javed, A.; Bhardwaj, V. A review on pyrazole derivatives of pharmacological potential. J. Pharm. Biomed. Sci., 2013, 3, 114-123.
[35]
Patil, S.B. Medicinal siganificance of pyrazole analogues: A review. J. Pharm. Sci. Res., 2020, 12, 402-404.
[36]
Sarafianos, S.G.; Hughes, S.H.; Arnold, E. Designing anti-AIDS drugs targeting the major mechanism of HIV-1 RT re-sistance to nucleoside analog drugs. Int. J. Biochem. Cell Biol., 2004, 36(9), 1706-1715.
[http://dx.doi.org/10.1016/j.biocel.2004.02.027] [PMID: 15183339]
[37]
El Safadi, Y.; Vivet-Boudou, V.; Marquet, R. HIV-1 reverse transcriptase inhibitors. Appl. Microbiol. Biotechnol., 2007, 75(4), 723-737.
[http://dx.doi.org/10.1007/s00253-007-0919-7] [PMID: 17370068]
[38]
Pau, A.K.; George, J.M. Antiretroviral therapy: current drugs. Infect. Dis. Clin., 2014, 28(3), 371-402.
[http://dx.doi.org/10.1016/j.idc.2014.06.001] [PMID: 25151562]
[39]
Arts, E.J.; Hazuda, D.J. HIV-1 antiretroviral drug therapy. Cold Spring Harb. Perspect. Med., 2012, 2(4), a007161.
[http://dx.doi.org/10.1101/cshperspect.a007161] [PMID: 22474613]
[40]
Chong, H.; Xue, J.; Zhu, Y.; Cong, Z.; Chen, T.; Guo, Y.; Wei, Q.; Zhou, Y.; Qin, C.; He, Y. Design of novel HIV-1/2 fusion inhibitors with high therapeutic efficacy in rhesus monkey models. J. Virol., 2018, 92(16), e00775-e18.
[http://dx.doi.org/10.1128/JVI.00775-18] [PMID: 29899103]
[41]
Fung, H.B.; Guo, Y. Enfuvirtide: a fusion inhibitor for the treatment of HIV infection. Clin. Ther., 2004, 26(3), 352-378.
[http://dx.doi.org/10.1016/S0149-2918(04)90032-X] [PMID: 15110129]
[42]
Kuritzkes, D.R. HIV-1 entry inhibitors: An overview. Curr. Opin. HIV AIDS, 2009, 4(2), 82-87.
[http://dx.doi.org/10.1097/COH.0b013e328322402e] [PMID: 19339945]
[43]
Guillemont, J.; Benjahad, A.; Oumouch, S.; Decrane, L.; Pal-andjian, P.; Vernier, D.; Queguiner, L.; Andries, K.; de Bé-thune, M-P.; Hertogs, K.; Grierson, D.S.; Nguyen, C.H. Syn-thesis and biological evaluation of C-5 methyl substituted 4-arylthio and 4-aryloxy-3-Iodopyridin-2(1H)-one type anti-HIV agents. J. Med. Chem., 2009, 52(23), 7473-7487.
[http://dx.doi.org/10.1021/jm900802y] [PMID: 19645483]
[44]
Mizuhara, T.; Oishi, S.; Ohno, H.; Shimura, K.; Matsuoka, M.; Fujii, N. Structure-activity relationship study of pyrim-ido[1,2-c][1,3]benzothiazin-6-imine derivatives for potent an-ti-HIV agents. Bioorg. Med. Chem., 2012, 20(21), 6434-6441.
[http://dx.doi.org/10.1016/j.bmc.2012.08.030] [PMID: 23022280]
[45]
Okazaki, S.; Mizuhara, T.; Shimura, K.; Murayama, H.; Ohno, H.; Oishi, S.; Matsuoka, M.; Fujii, N. Identification of anti-HIV agents with a novel benzo[4,5]isothiazolo[2,3-a]pyrimidine scaffold. Bioorg. Med. Chem., 2015, 23(7), 1447-1452.
[http://dx.doi.org/10.1016/j.bmc.2015.02.015] [PMID: 25744188]
[46]
Wu, Y.; Tang, C.; Rui, R.; Yang, L.; Ding, W.; Wang, J.; Li, Y.; Lai, C.C.; Wang, Y.; Luo, R.; Xiao, W.; Zhang, H.; Zheng, Y.; He, Y. Synthesis and biological evaluation of a series of 2-(((5-akly/aryl-1H-pyrazol-3-yl)methyl)thio)-5-alkyl-6-(cyclohexylmethyl)-pyrimidin-4(3H)-ones as potential HIV-1 inhibitors. Acta Pharm. Sin. B, 2020, 10(3), 512-528.
[http://dx.doi.org/10.1016/j.apsb.2019.08.009] [PMID: 32140396]
[47]
Seto, M.; Aramaki, Y.; Okawa, T.; Miyamoto, N.; Aikawa, K.; Kanzaki, N.; Niwa, S.; Iizawa, Y.; Baba, M.; Shiraishi, M. Orally active CCR5 antagonists as anti-HIV-1 agents: synthe-sis and biological activity of 1-benzothiepine 1,1-dioxide and 1-benzazepine derivatives containing a tertiary amine moiety. Chem. Pharm. Bull. (Tokyo), 2004, 52(5), 577-590.
[http://dx.doi.org/10.1248/cpb.52.577] [PMID: 15133211]
[48]
Seto, M.; Aramaki, Y.; Imoto, H.; Aikawa, K.; Oda, T.; Kanzaki, N.; Iizawa, Y.; Baba, M.; Shiraishi, M. Orally active CCR5 antagonists as anti-HIV-1 agents 2: Synthesis and bio-logical activities of anilide derivatives containing a pyridine N-oxide moiety. Chem. Pharm. Bull. (Tokyo), 2004, 52(7), 818-829.
[http://dx.doi.org/10.1248/cpb.52.818] [PMID: 15256702]
[49]
El Otmani, B.; El Mahi, M.; Essassi, E.; Bakri, Y.; Benjouad, A. Synthese Et Effet Vih Des Pyrazolyl (Isoxazolyl) Pyrido [1, 2-a]. Pyrimidines. Moroccan J. Heterocycl. Chem., 2005, 4, 26-38.
[50]
Rizvi, S.U.F.; Siddiqui, H.L.; Johns, M.; Detorio, M.; Schina-zi, R.F. Anti-HIV-1 and cytotoxicity studies of piperidyl-thienyl chalcones and their 2-pyrazoline derivatives. Med. Chem. Res., 2012, 21, 3741-3749.
[http://dx.doi.org/10.1007/s00044-011-9912-x]
[51]
Cho, J.H.; Coats, S.J.; Schinazi, R.F. Synthesis of carbocyclic nucleoside analogs with five-membered heterocyclic nucleo-bases. Tetrahedron Lett., 2015, 56(23), 3587-3590.
[http://dx.doi.org/10.1016/j.tetlet.2015.01.051] [PMID: 26028788]
[52]
Cox, B.D.; Prosser, A.R.; Sun, Y.; Li, Z.; Lee, S.; Huang, M.B.; Bond, V.C.; Snyder, J.P.; Krystal, M.; Wilson, L.J.; Liotta, D.C. Pyrazolo-piperidines exhibit dual inhibition of CCR5/CXCR4 HIV entry and reverse transcriptase. ACS Med. Chem. Lett., 2015, 6(7), 753-757.
[http://dx.doi.org/10.1021/acsmedchemlett.5b00036] [PMID: 26191361]
[53]
Messore, A.; Corona, A.; Madia, V.N.; Saccoliti, F.; Tudino, V.; De Leo, A.; Scipione, L.; De Vita, D.; Amendola, G.; Di Maro, S.; Novellino, E.; Cosconati, S.; Métifiot, M.; Andreola, M.L.; Valenti, P.; Esposito, F.; Grandi, N.; Tramontano, E.; Costi, R.; Di Santo, R. Pyrrolyl pyrazoles as non-diketo acid inhibitors of the HIV-1 ribonuclease H function of reverse transcriptase. ACS Med. Chem. Lett., 2020, 11(5), 798-805.
[http://dx.doi.org/10.1021/acsmedchemlett.9b00617] [PMID: 32435387]
[54]
Shen, D.M.; Shu, M.; Mills, S.G.; Chapman, K.T.; Malkowitz, L.; Springer, M.S.; Gould, S.L.; DeMartino, J.A.; Siciliano, S.J.; Kwei, G.Y.; Carella, A.; Carver, G.; Holmes, K.; Schleif, W.A.; Danzeisen, R.; Hazuda, D.; Kessler, J.; Lineberger, J.; Miller, M.D.; Emini, E.A. Antagonists of human CCR5 recep-tor containing 4-(pyrazolyl)piperidine side chains. Part 1: Discovery and SAR study of 4-pyrazolylpiperidine side chains. Bioorg. Med. Chem. Lett., 2004, 14(4), 935-939.
[http://dx.doi.org/10.1016/j.bmcl.2003.12.004] [PMID: 15012997]
[55]
Ali, M.A.; Yar, M.S.; Siddiqui, A.A.; Sriram, D.; Yogeeswari, P.; De Clercq, E. Synthesis and anti-HIV activity of N&-nicotinoyl--3-(4&-hydroxy-3&-methylphenyl)-5-[substituted phenyl]-2-pyrazolines. Acta Pol. Pharm., 2007, 64(5), 423-428.
[PMID: 18540162]
[56]
Madni, M.; Hameed, S.; Ahmed, M.N.; Tahir, M.N.; Al-Masoudi, N.A.; Pannecouque, C. Synthesis, crystal structure, anti-HIV, and antiproliferative activity of new pyrazolylthia-zole derivatives. Med. Chem. Res., 2017, 26, 2653-2665.
[http://dx.doi.org/10.1007/s00044-017-1963-1]
[57]
Amr, A.; Abdalla, M.; Essaouy, S.; Areef, M.; Elgamal, M.; Nassear, T.; Haschich, A.; Al-Omar, M. Synthesis of some substituted 5H-furo [3, 2-g] chromene and benzofuran sul-fonate derivatives as potent anti-HIV agents. Russ. J. Gen. Chem., 2017, 87, 1591-1600.
[http://dx.doi.org/10.1134/S1070363217070246]
[58]
Kumar, S.; Gupta, S.; Gaikwad, S.; Abadi, L.F.; Bhutani, L.K.K.; Kulkarni, S.; Singh, I.P. Design, synthesis and in vitro evaluation of novel anti-HIV 3-pyrazol-3-yl-pyridin-2-one analogs. Med. Chem., 2019, 15(5), 561-570.
[http://dx.doi.org/10.2174/1573406414666181106125539] [PMID: 30398119]
[59]
Mowbray, C.E.; Burt, C.; Corbau, R.; Perros, M.; Tran, I.; Stupple, P.A.; Webster, R.; Wood, A. Pyrazole NNRTIs 1: De-sign and initial optimisation of a novel template. Bioorg. Med. Chem. Lett., 2009, 19(19), 5599-5602.
[http://dx.doi.org/10.1016/j.bmcl.2009.08.039] [PMID: 19709880]
[60]
Mowbray, C.E.; Corbau, R.; Hawes, M.; Jones, L.H.; Mills, J.E.; Perros, M.; Selby, M.D.; Stupple, P.A.; Webster, R.; Wood, A. Pyrazole NNRTIs 3: Optimisation of physicochem-ical properties. Bioorg. Med. Chem. Lett., 2009, 19(19), 5603-5606.
[http://dx.doi.org/10.1016/j.bmcl.2009.08.043] [PMID: 19717303]
[61]
Mowbray, C.E.; Burt, C.; Corbau, R.; Gayton, S.; Hawes, M.; Perros, M.; Tran, I.; Price, D.A.; Quinton, F.J.; Selby, M.D.; Stupple, P.A.; Webster, R.; Wood, A. Pyrazole NNRTIs 4: se-lection of UK-453,061 (lersivirine) as a development candi-date. Bioorg. Med. Chem. Lett., 2009, 19(20), 5857-5860.
[http://dx.doi.org/10.1016/j.bmcl.2009.08.080] [PMID: 19748778]
[62]
Platten, M.; Fätkenheuer, G. Lersivirine - a new drug for HIV infection therapy. Expert Opin. Investig. Drugs, 2013, 22(12), 1687-1694.
[http://dx.doi.org/10.1517/13543784.2013.846325] [PMID: 24128277]
[63]
Fichez, J.; Soulie, C.; Le Corre, L.; Sayon, S.; Priet, S.; Alva-rez, K.; Delelis, O.; Gizzi, P.; Prestat, G.; Gravier-Pelletier, C.; Marcelin, A.G.; Calvez, V.; Busca, P. Discovery, SAR study and ADME properties of methyl 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate as an HIV-1 replication inhibitor. RSC Med. Chem., 2020, 11(5), 577-582.
[http://dx.doi.org/10.1039/D0MD00025F] [PMID: 33479659]
[64]
Yan, R-Z.; Liu, X-Y.; Xu, W-F.; Pannecouque, C.; Witvrouw, M.; De Clercq, E. Synthesis and anti-HIV evaluation of the novel 2-(m-chlorobenzyl)-4-substituted-7-methyl-1, 1, 3-trioxo-pyrazolo[4, 5-e] [1, 2, 4]thiadiazines. Arch. Pharm. Res., 2006, 29(11), 957-962.
[http://dx.doi.org/10.1007/BF02969278] [PMID: 17146963]
[65]
Liu, X.Y.; Yan, R.Z.; Chen, N.G.; Xu, W.F. Regioselective synthesis and anti-HIV activity of the novel 2-and 4-substituted pyrazolo [4, 5-e][1, 2, 4] thiadiazines. Chin. Chem. Lett., 2007, 18, 137-140.
[http://dx.doi.org/10.1016/j.cclet.2006.12.006]
[66]
Tucker, T.J.; Saggar, S.; Sisko, J.T.; Tynebor, R.M.; Williams, T.M.; Felock, P.J.; Flynn, J.A.; Lai, M-T.; Liang, Y.; McGaughey, G.; Liu, M.; Miller, M.; Moyer, G.; Munshi, V.; Perlow-Poehnelt, R.; Prasad, S.; Sanchez, R.; Torrent, M.; Vacca, J.P.; Wan, B.L.; Yan, Y. The design and synthesis of diaryl ether second generation HIV-1 Non-Nucleoside Re-verse Transcriptase Inhibitors (NNRTIs) with enhanced po-tency versus key clinical mutations. Bioorg. Med. Chem. Lett., 2008, 18(9), 2959-2966.
[http://dx.doi.org/10.1016/j.bmcl.2008.03.064] [PMID: 18396399]
[67]
Tucker, T.J.; Sisko, J.T.; Tynebor, R.M.; Williams, T.M.; Felock, P.J.; Flynn, J.A.; Lai, M-T.; Liang, Y.; McGaughey, G.; Liu, M. Discovery of 3-{5-[(6-amino-1H-pyrazolo [3, 4-b] pyridine-3-yl) methoxy]-2-chlorophenoxy}-5-chlorobenzonitrile (MK-4965): a potent, orally bioavailable HIV-1 non-nucleoside reverse transcriptase inhibitor with improved potency against key mutant viruses. J. Med. Chem., 2008, 51, 6503-6511.
[http://dx.doi.org/10.1021/jm800856c] [PMID: 18826204]
[68]
Ahmad, M.; Aslam, S.; Bukhari, M.H.; Montero, C.; Detorio, M.; Parvez, M.; Schinazi, R.F. Synthesis of novel pyrazolo-benzothiazine 5, 5-dioxide derivatives as potent anti-HIV-1 agents. Med. Chem. Res., 2014, 23, 1309-1319.
[http://dx.doi.org/10.1007/s00044-013-0718-x]
[69]
Khalid, Z.; Aslam, S.; Ahmad, M.; Munawar, M.A.; Montero, C.; Detorio, M.; Parvez, M.; Schinazi, R.F. Anti-HIV activity of new pyrazolobenzothiazine 5,5-dioxide-based acetohydra-zides. Med. Chem. Res., 2015, 24(10), 3671-3680.
[http://dx.doi.org/10.1007/s00044-015-1411-z] [PMID: 34316244]
[70]
Aslam, S.; Ahmad, M.; Zia-Ur-Rehman, M.; Montero, C.; Detorio, M.; Parvez, M.; Schinazi, R.F. Synthesis and anti-HIV-1 screening of novel N&-(1-(aryl)ethylidene)-2-(5,5-dioxido-3-phenylbenzo[e] pyrazolo[4,3-c][1,2]thiazin-4(1H)-yl)acetohydrazides. Arch. Pharm. Res., 2014, 37(11), 1380-1393.
[http://dx.doi.org/10.1007/s12272-013-0200-9] [PMID: 23835833]
[71]
Aslam, S.; Ahmad, M.; Athar, M.M.; Ashfaq, U.A.; Gardiner, J.M.; Montero, C.; Detorio, M.; Parvez, M.; Schinazi, R.F. Synthesis, molecular docking and antiviral screening of novel N&-substitutedbenzylidene-2-(4-methyl-5, 5-dioxido-3-phenylbenzo [e] pyrazolo [4, 3-c][1, 2] thiazin-1 (4H)-yl) acetohydrazides. Med. Chem. Res., 2014, 23, 2930-2946.
[http://dx.doi.org/10.1007/s00044-013-0879-7]
[72]
Gomha, S.M.; Badrey, M.G.; Abdalla, M.M.; Arafa, R.K. Novel anti-HIV-1 NNRTIs based on a pyrazolo [4, 3-d] isox-azole backbone scaffold: Design, synthesis and insights into the molecular basis of action. MedChemComm, 2014, 5, 1685-1692.
[http://dx.doi.org/10.1039/C4MD00282B]
[73]
Tian, Y.; Du, D.; Rai, D.; Wang, L.; Liu, H.; Zhan, P.; De Clercq, E.; Pannecouque, C.; Liu, X. Fused heterocyclic com-pounds bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 1: Design, synthesis and biological evaluation of novel 5,7-disubstituted pyrazolo[1,5-a]pyrimidine derivatives. Bioorg. Med. Chem., 2014, 22(7), 2052-2059.
[http://dx.doi.org/10.1016/j.bmc.2014.02.029] [PMID: 24631361]
[74]
Liu, G-N.; Luo, R-H.; Zhou, Y.; Zhang, X-J.; Li, J.; Yang, L-M.; Zheng, Y-T.; Liu, H. Synthesis and anti-HIV-1 activity evaluation for novel 3a, 6a-dihydro-1H-pyrrolo [3, 4-c] pyra-zole-4, 6-dione derivatives. Molecules, 2016, 21(9), 1198.
[http://dx.doi.org/10.3390/molecules21091198] [PMID: 27617994]
[75]
Kasralikar, H.M.; Jadhavar, S.C.; Goswami, S.V.; Kaminwar, N.S.; Bhusare, S.R. Design, synthesis and molecular docking of pyrazolo [3,4d] thiazole hybrids as potential anti-HIV-1 NNRT inhibitors. Bioorg. Chem., 2019, 86, 437-444.
[http://dx.doi.org/10.1016/j.bioorg.2019.02.006] [PMID: 30771690]
[76]
Savant, M.M.; Ladva, K.D.; Pandit, A.B. Facile synthesis of highly functionalized novel pyrazolopyridones using oxo-ketene dithioacetal and their anti-HIV activity. Synth. Commun., 2018, 48, 1640-1648.
[http://dx.doi.org/10.1080/00397911.2018.1458239]
[77]
Kumar, S.; Gupta, S.; Abadi, L.F.; Gaikwad, S.; Desai, D.; Bhutani, K.K.; Kulkarni, S.; Singh, I.P. Synthesis and in-vitro anti-HIV-1 evaluation of novel pyrazolo[4,3-c]pyridin-4-one derivatives. Eur. J. Med. Chem., 2019, 183, 111714.
[http://dx.doi.org/10.1016/j.ejmech.2019.111714] [PMID: 31557609]
[78]
Patel, M.; Cianci, C.; Allard, C.W.; Parker, D.D.; Simmerma-cher, J.; Jenkins, S.; Mcauliffe, B.; Minassian, B.; Discotto, L.; Krystal, M.; Meanwell, N.A.; Naidu, B.N. Design, synthesis and SAR study of novel C2-pyrazolopyrimidine amides and amide isosteres as allosteric integrase inhibitors. Bioorg. Med. Chem. Lett., 2020, 30(21), 127516.
[http://dx.doi.org/10.1016/j.bmcl.2020.127516] [PMID: 32860982]

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