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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 53, 2023 - Issue 10
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Articles

Synthesis of novel acridines, tetrahydrodipyrazolo [3,4-b:4',3'-e]pyridines, tri-substituted methanes (TRSMs) bearing 2-(4-(1-phenyl-1H-pyrazol-3-yl)phenoxy)-N-phenylacetamide unit as novel hybrid molecules

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Pages 696-707 | Received 12 Jan 2023, Published online: 30 Mar 2023

References

  • Isambert, N.; Duque, M. d M.; Plaquevent, J.-C.; Génisson, Y.; Rodriguez, J.; Constantieux, T. Chem. Soc. Rev. 2011, 40, 1347–1357. DOI: 10.1039/c0cs00013b.
  • Shiri, M. Chem. Rev. 2012, 112, 3508–3549. DOI: 10.1021/cr2003954.
  • Dömling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083–3135. DOI: 10.1021/cr100233r.
  • Brauch, S.; van Berkel, S. S.; Westermann, B. Chem. Soc. Rev. 2013, 42, 4948–4962. DOI: 10.1039/c3cs35505e.
  • Maleki, A.; Hassanzadeh-Afruzi, F.; Varzi, Z.; Esmaeili, M. S. Mater. Sci. Eng. C. Mater. Biol. Appl. 2020, 109, 110502. DOI: 10.1016/j.msec.2019.110502.
  • Alqasoumi, S. I.; Al-Taweel, A. M.; Alafeefy, A. M.; Hamed, M. M.; Noaman, E.; Ghorab, M. M. Bioorg. Med. Chem. Lett. 2009, 19, 6939–6942. DOI: 10.1016/j.bmcl.2009.10.065.
  • Ghozlan, S. A. S.; Mohamed, M. F.; Ahmed, A. G.; Shouman, S. A.; Attia, Y. M.; Abdelhamid, I. A. Arch. Pharm. 2015, 348, 113–124. DOI: 10.1002/ardp.201400304.
  • Nia, R. H.; Mamaghani, M.; Shirini, F.; Tabatabaeian, K.; Heidary, M. Org. Prep. Proced. Int. 2014, 46, 152–163. DOI: 10.1080/00304948.2014.884372.
  • Manpadi, M.; Uglinskii, P. Y.; Rastogi, S. K.; Cotter, K. M.; Wong, Y.-S. C.; Anderson, L. A.; Ortega, A. J.; Van Slambrouck, S.; Steelant, W. F. A.; Rogelj, S.; et al. Org. Biomol. Chem. 2007, 5, 3865–3872. DOI: 10.1039/b713820b.
  • Da Rocha Pitta, M. G.; Souza, É. S.; Barros, F. W. A.; Moraes Filho, M. O.; Pessoa, C. O.; Hernandes, M. Z.; Do Carmo Alves De Lima, M.; Galdino, S. L.; Da Rocha Pitta, I. Med. Chem. Res. 2013, 22, 2421–2429. DOI: 10.1007/s00044-012-0236-2.
  • Ghorab, M.; Ragab, F.; Noaman, E.; Heiba, H.; El-Hossary, E. Arzneimittelforschung. 2007, 57, 795–803. DOI: 10.1055/s-0031-1296682.
  • Goodell, J. R.; Madhok, A. A.; Hiasa, H.; Ferguson, D. M. Bioorg. Med. Chem. 2006, 14, 5467–5480. DOI: 10.1016/j.bmc.2006.04.044.
  • Muscia, G. C.; Buldain, G. Y.; Asís, S. E. Eur. J. Med. Chem. 2014, 73, 243–249. DOI: 10.1016/j.ejmech.2013.12.013.
  • El-Sabbagh, O. I.; Rady, H. M. Eur. J. Med. Chem. 2009, 44, 3680–3686. DOI: 10.1016/j.ejmech.2009.04.001.
  • Lyakhov, S. A.; Suveyzdis, Y. I.; Litvinova, L. A.; Andronati, S. A.; Rybalko, S. L.; Dyadyun, S. T. Pharmazie. 2000, 55, 733–736.
  • Baguley, B. C.; Cain, B. F. Mol. Pharmacol. 1982, 22, 486–492.
  • Denny, W. A.; Cain, B. F. J. Med. Chem. 1978, 21, 430–437. DOI: 10.1021/jm00203a005.
  • Sondhi, S. M.; Singh, J.; Rani, R.; Gupta, P. P.; Agrawal, S. K.; Saxena, A. K. Eur. J. Med. Chem. 2010, 45, 555–563. DOI: 10.1016/j.ejmech.2009.10.042.
  • Nath, M.; Vats, M.; Roy, P. Inorganica Chim. Acta. 2014, 423, 70–82. DOI: 10.1016/j.ica.2014.02.034.
  • Benoit, A. R.; Schiaffo, C.; Salomon, C. E.; Goodell, J. R.; Hiasa, H.; Ferguson, D. M. Bioorg. Med. Chem. Lett. 2014, 24, 3014–3017. DOI: 10.1016/j.bmcl.2014.05.037.
  • Belmont, P.; Bosson, J.; Godet, T.; Tiano, M. Anticancer. Agents Med. Chem. 2007, 7, 139–169. DOI: 10.2174/187152007780058669.
  • Kendre, B. V.; Landge, M. G.; Bhusare, S. R. Arab. J. Chem. 2015, 12, 2091–2097. DOI: 10.1016/j.arabjc.2015.01.007.
  • Viveka, S.; Dinesha; Madhu, L. N.; Nagaraja, G. K. Monatsh. Chem. 2015, 146, 1547–1555. DOI: 10.1007/s00706-015-1428-5.
  • Metwally, N. H.; Badawy, M. A.; Okpy, D. S. Chem. Pharm. Bull. 2015, 63, 495–503. DOI: 10.1248/cpb.c14-00885.
  • Alam, R.; Wahi, D.; Singh, R.; Sinha, D.; Tandon, V.; Grover, A.; Rahisuddin . Bioorg. Chem. 2016, 69, 77–90. DOI: 10.1016/j.bioorg.2016.10.001.
  • Kaushik, D.; Khan, S. A.; Chawla, G.; Kumar, S. Eur. J. Med. Chem. 2010, 45, 3943–3949. DOI: 10.1016/j.ejmech.2010.05.049.
  • Sallam, H. A.; Elgubbi, A. S.; El-Helw, E. A. E. Synth. Commun. 2020, 50, 2066–2077. DOI: 10.1080/00397911.2020.1765258.
  • Bellam, M.; Gundluru, M.; Sarva, S.; Chadive, S.; Netala, V. R.; Tartte, V.; Cirandur, S. R. Chem. Heterocycl. Compd. 2017, 53, 173–178. DOI: 10.1007/s10593-017-2036-6.
  • Farghaly, A. A.; Bekhit, A. A.; Park, J. Y. Arch. Pharm. 2000, 333, 53–57. DOI: 10.1002/(SICI)1521-4184(200002)333:2/3<53::AID-ARDP53>3.0.CO;2-E.
  • Mary, S. J. J.; Siddique, M. U. M.; Pradhan, S.; Jayaprakash, V.; James, C. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2021, 244, 118825. DOI: 10.1016/j.saa.2020.118825.
  • Severina, H. I.; Skupa, O. O.; Voloshchuk, N. I.; Georgiyants, V. A. J. Appl. Pharm. Sci. 2020, 10, 1–8.
  • Yusov, A. S.; Chashchina, S. V.; Mikhailovskii, A. G.; Rudakova, I. P. Pharm. Chem. J. 2019, 53, 35–39. DOI: 10.1007/s11094-019-01951-y.
  • Khazir, J.; Mir, B. A.; Chashoo, G.; Maqbool, T.; Riley, D.; Pilcher, L. J. Heterocycl. Chem. 2020, 57, 1306–1318. DOI: 10.1002/jhet.3867.
  • Bhavsar, D.; Trivedi, J.; Parekh, S.; Savant, M.; Thakrar, S.; Bavishi, A.; Radadiya, A.; Vala, H.; Lunagariya, J.; Parmar, M. Bioorg. Med. Chem. Lett. 2011, 21, 3443–3446. DOI: 10.1016/j.bmcl.2011.03.105.
  • Yele, V.; Azam, M. A.; Wadhwani, A. D. Chem. Biodivers. 2021, 18, e2000907. DOI: 10.1002/cbdv.202000907.
  • Mikhailovskii, A. G.; Pogorelova, E. S.; Pershina, N. N.; Makhmudov, R. R.; Novikova, V. V. Pharm. Chem. J. 2020, 53, 1013–1017. DOI: 10.1007/s11094-020-02115-z.
  • Gull, Y.; Rasool, N.; Noreen, M.; Altaf, A. A.; Musharraf, S. G.; Zubair, M.; Nasim, F. U. H.; Yaqoob, A.; DeFeo, V.; Zia-Ul-Haq, M. Molecules. 2016, 21, 1–17.
  • Ang, W.; Lin, Y. N.; Yang, T.; Yang, J. Z.; Pi, W. Y.; Yang, Y. H.; Luo, Y. F.; Deng, Y.; Wei, Y. Q. Molecules. 2012, 17, 2248–2258. DOI: 10.3390/molecules17022248.
  • Ölgen, S.; Bakar, F.; Aydin, S.; Nebioğlu, D.; Nebioğlu, S. J. Enzyme Inhib. Med. Chem. 2013, 28, 58–64. DOI: 10.3109/14756366.2011.631183.
  • Al-Qawasmeh, R. A.; Lee, Y.; Cao, M. Y.; Gu, X.; Vassilakos, A.; Wright, J. A.; Young, A. Bioorg. Med. Chem. Lett. 2004, 14, 347–350. DOI: 10.1016/j.bmcl.2003.11.004.
  • Shagufta; Srivastava, A. K.; Sharma, R.; Mishra, R.; Balapure, A. K.; Murthy, P. S. R.; Panda, G. Bioorg. Med. Chem. 2009, 14, 1497–1505.
  • Panda, G.; Parai, M. K.; Das, S. K.; Sinha, M.; Chaturvedi, V.; Srivastava, A. K.; Manju, Y. S.; Gaikwad, A. N.; Sinha, S.; Shagufta . Eur. J. Med. Chem. 2007, 42, 410–419. DOI: 10.1016/j.ejmech.2006.09.020.
  • Kumar, A.; Panda, G.; Siddiqi, M. I.; Shagufta . J. Mol. Model. 2007, 13, 99–109. DOI: 10.1007/s00894-006-0124-0.
  • Martínez, R.; Espinosa, A.; Tárraga, A.; Molina, P. Tetrahedron. 2008, 64, 2184–2191. DOI: 10.1016/j.tet.2007.12.025.
  • Emmadi, N. R.; Atmakur, K.; Bingi, C.; Godumagadda, N. R.; Chityal, G. K.; Nanubolu, J. B. Bioorg. Med. Chem. Lett. 2014, 24, 485–489. DOI: 10.1016/j.bmcl.2013.12.038.
  • Jung, J. C.; Park, O. S. Molecules. 2009, 14, 4790–4803. DOI: 10.3390/molecules14114790.
  • Tantawy, M. A.; Sroor, F. M.; Mohamed, M. F.; El-Naggar, M. E.; Saleh, F. M.; Hassaneen, H. M.; Abdelhamid, I. A. Anticancer. Agents Med. Chem. 2019, 20, 70–83.
  • Al-Awadi, N. A.; Ibrahim, M. R.; Abdelhamid, I. A.; Elnagdi, M. H. Tetrahedron. 2008, 64, 8202–8205. DOI: 10.1016/j.tet.2008.06.026.
  • Sroor, F. M.; Aboelenin, M. M.; Mahrous, K. F.; Mahmoud, K.; Elwahy, A. H. M.; Abdelhamid, I. A. Arch. Pharm. 2020, 353, 2000069. DOI: 10.1002/ardp.202000069.
  • Al-Awadi, N. A.; Abdelhamid, I. A.; Al-Etaibi, A. M.; Elnagdi, M. H. Synlett. 2007, 2205–2208. DOI: 10.1055/s-2007-985573.
  • WalyEldeen, A. A.; Sabet, S.; El-Shorbagy, H. M.; Abdelhamid, I. A.; Ibrahim, S. A. Chem. Biol. Interact. 2023, 369, 110297. DOI: 10.1016/j.cbi.2022.110297.
  • Abdelhamid, I. A.; Shaaban, M. R.; Elwahy, A. H. M. Bis-Aldehydes: Versatile Precursors for Bis-Heterocycles. Adv. Heterocycl.Chem., 2023, 139, 135–200. DOI: 10.1016/bs.aihch.2022.10.004
  • Mohamed, M. F.; Ibrahim, N. S.; Saddiq, A. A.; Almaghrabi, O. A.; Al-Hazemi, M. E.; Hassaneen, H. M.; Abdelhamid, I. A. Naunyn. Schmiedebergs. Arch. Pharmacol. 2022, 396, 1–18.
  • Al-Awadi, N. A.; Abdelkhalik, M. M.; Abdelhamid, I. A.; Elnagdi, M. H. Synlett. 2007, 2007, 2979–2982. DOI: 10.1055/s-2007-992355.
  • Mohamed, M. F.; Mohamed, M. S.; Fathi, M. M.; Shouman, S. A.; Abdelhamid, I. A. Anticancer. Agents Med. Chem. 2014, 14, 1282–1292. DOI: 10.2174/187152061409141010114547.
  • Abdelmoniem, A. M.; Hassaneen, H. M. E.; Abdelhamid, I. A. J. Heterocycl. Chem. 2016, 53, 2084–2090. DOI: 10.1002/jhet.2480.
  • Abdella, A. M.; Abdelmoniem, A. M.; Abdelhamid, I. A.; Elwahy, A. H. M. J. Heterocycl. Chem. 2020, 57, 1476–1523. DOI: 10.1002/jhet.3883.
  • Ghozlan, S. A. S.; Mohamed, M. H.; Abdelmoniem, A. M.; Abdelhamid, I. A. Arkivoc. 2009, 2009, 302–311. DOI: 10.3998/ark.5550190.0010.a27.
  • Ghozlan, S. A. S.; Abdelhamid, I. A. A.; Elnagdi, M. H. H. Arkivoc. 2006, 147–157. DOI: 10.3998/ark.5550190.0007.d15.
  • Mahmoud, H. K.; Selim, N. H. M.; Elwahy, A. H. M.; Abdelhamid, I. A.; Diab, H. M. Polycycl. Aromat. Compd. 2022, 1–13. DOI: 10.1080/10406638.2022.2151476.
  • Diab, H. M.; Abdelhamid, I. A.; Elwahy, A. H. M. Synlett. 2018, 29, 1627–1633.
  • Mohamed, M. F.; Abdelmoniem, A. M.; Elwahy, A. H. M.; Abdelhamid, I. A. Curr. Cancer Drug Targets. 2018, 18, 372–381. DOI: 10.2174/1568009617666170630143311.
  • Elwahy, A. H. M.; Shaaban, M. R. Heterocycles. 2017, 94, 595–655. DOI: 10.3987/REV-16-854.
  • Elwahy, A. H. M.; Darweesh, A. F.; Shaaban, M. R. J. Heterocycl. Chem. 2012, 49, 1120–1125. DOI: 10.1002/jhet.952.
  • Shaaban, M. R.; Elwahy, A. H. M. J. Heterocycl. Chem. 2012, 49, 640–645. DOI: 10.1002/jhet.861.
  • Ginidi, A. R. S.; Shaaban, M. R.; Farag, A. M.; Elwahy, A. H. M. J. Heterocycl. Chem. 2015, 52, 1421–1428. DOI: 10.1002/jhet.2223.
  • Shaaban, M. R.; Elwahy, A. H. M. Curr. Org. Synth. 2013, 10, 425–466. DOI: 10.2174/1570179411310030007.
  • De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. Synlett. 2004, 2004, 2299–2302.
  • Abdelhamid, I. A.; Shaaban, M. R.; Elwahy, A. H. M. Adv. Heterocycl. Chem. 2022, 136, 171–223. DOI: 10.1016/bs.aihch.2021.08.001.
  • Abdelmoniem, A. M.; Ghozlan, S. A. S.; Butenschön, H.; Abdelmoniem, D. M.; Elwahy, A. H. M.; Abdelhamid, I. A. Arkivoc. 2019, 2019, 163–177. DOI: 10.24820/ark.5550190.p010.875.
  • Fakheri-Vayeghan, S.; Abdolmohammadi, S.; Kia-Kojoori, R. Z. Naturforsch. B. 2018, 73, 545–551. DOI: 10.1515/znb-2018-0030.
  • Basumatary, G.; Mohanta, R.; Bez, G. Catal. Letters. 2019, 149, 2776–2786. DOI: 10.1007/s10562-019-02809-4.
  • Foroughi, H. O.; Kargar, M.; Erjaee, Z.; Zarenezhad, E. Monatsh. Chem. 2020, 151, 1603–1608.

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