Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 17
223
Views
11
CrossRef citations to date
0
Altmetric
Articles

Design, synthesis, antitubercular and antibacterial activities of pyrrolo[3,2-b]pyridine-3-carboxamide linked 2-methoxypyridine derivatives and in silico docking studies

, , , , , & show all
Pages 2219-2234 | Received 15 Mar 2019, Published online: 25 May 2019

References

  • World Health Organisation. Global Tuberculosis Report, to be found under, 2016. http://apps.who.int/iris/bitstream/10665/250441/1/9789241565394-eng.pdf?ua=1 (accessed Dec 12, 2016).
  • Shirude, P. S.; Shandil, R.; Sadler, C.; Naik, M.; Hosagrahara, V.; Hameed, S.; Shinde, V.; Bathula, C.; Humnabadkar, V.; Kumar, N.; et al. Azaindoles: Noncovalent DprE1 Inhibitors from Scaffold Morphing Efforts, Kill Mycobacterium Tuberculosis and Are Efficacious in vivo. J. Med. Chem. 2013, 56, 9701–9708. DOI: 10.1021/jm401382v.
  • Shirude, P. S.; Shandil, R. K.; Manjunatha, M. R.; Sadler, C.; Panda, M.; Panduga, V.; Reddy, J.; Saralaya, R.; Nanduri, R.; Ambady, A.; et al. Lead Optimization of 1,4-Azaindoles as Antimycobacterial Agents. J. Med. Chem. 2014, 57, 5728–5737. DOI: 10.1021/jm500571f.
  • Chatterji, M.; Shandil, R.; Manjunatha, M. R.; Solapure, S.; Ramachandran, V.; Kumar, N.; Saralaya, R.; Panduga, V.; Reddy, J.; Prabhakar, K. R.; et al. 1, 4-azaindole: potential drug candidate for the treatment of tuberculosis. Antimicrobl. Agents and Chemother. 2014, 58, 5325–5331. DOI: 10.1128/AAC.03233-14.
  • Bayomi, S. M.; Price, K. E.; Sowell, J. W., Sr. Synthesis of 7-Oxopyrrolo[3,2-B]Pyridine-6-Carboxylic Acid Derivatives as Potential Antimicrobial Agents. J. Heterocycl. Chem. 1985, 22, 83–88. DOI: 10.1002/jhet.5570220122.
  • Jeschke, P.; Harder, A.; Etzel, W.; Gau, w.; Göhrt, A.; Buchholz, J. B.; Thielking, G. Synthesis and Anthelmintic Activity of 7-Substituted 3,4a-Dimethyl-4a,5a,8a,8b-Tetrahydro-6H-Pyrrolo[3′,4′:4,5]Furo[3,2-b]Pyridine-6,8(7H)-Diones. Bioorg. Med. Chem. Lett. 2005, 15, 2375–2379. DOI: 10.1016/j.bmcl.2005.02.089.
  • Carbone, A.; Pennati, M.; Barraja, P.; Montalbano, A.; Parrino, B.; Spano, V.; Lopergolo, A.; Sbarra, S.; Doldi, V.; Zaffaroni, N.; et al. Synthesis and Antiproliferative Activity of Substituted 3[2-(1H-Indol-3-yl)- 1,3-Thiazol-4-yl]-1H-Pyrrolo[3,2-b]Pyridines, Marine Alkaloid Nortopsentin Analogues. CMC. 2014, 21, 1654–1666. DOI: 10.2174/09298673113206660307.
  • Carbone, A.; Pennati, M.; Parrino, B.; Lopergolo, A.; Barraja, P.; Montalbano, A.; Spanò, V.; Sbarra, S.; Doldi, V.; De Cesare, M.; et al. Novel 1 H -Pyrrolo[2,3- b ]Pyridine Derivative Nortopsentin Analogues: Synthesis and Antitumor Activity in Peritoneal Mesothelioma Experimental Models. J. Med. Chem. 2013, 56, 7060–7072. DOI: 10.1021/jm400842x.
  • Timmins, G. S.; Deretic, V. Mechanisms of Action of Isoniazid. Mol. Microbiol. 2006, 62, 1220–1227. DOI: 10.1111/j.1365-2958.2006.05467.x.
  • Katz, R. B.; Voyle, M. Synthesis of Some Nitropyridylacetonitriles. Synthesis. 1989, 1989, 314–316. DOI: 10.1055/s-1989-27239.
  • Shanshan, G.; Qi, S. A practical synthesis of 4-azaindole. Adv. Mater. Res. 2014, 859, 353–356.
  • Chikhale, R.; Menghani, S.; Babu, R.; Bansode, R.; Bhargavi, G.; Karodia, N.; Rajasekharan, M. V.; Paradkar, A.; Khedekar, P. P. Development of Selective DprE1 Inhibitors: Design, Synthesis, Crystal Structure and Antitubercular Activity of Benzothiazolylpyrimidine-5-Carboxamides. Eur. J. Med. Chem. 2015, 96, 30–46. DOI: 10.1016/j.ejmech.2015.04.011.
  • Chitre, T. S.; Asgaonkar, K. D.; Miniyar, P. B.; Dharme, A. B.; Arkile, M. A.; Yeware, A.; Sarkar, D.; Khedkar, V. M.; Jha, P. C. Synthesis and Docking Studies of Pyrazine-Thiazolidinone Hybrid Scaffold Targeting Dormant Tuberculosis. Bioorg. Med. Chem. Lett. 2016, 26, 2224–2228. DOI: 10.1016/j.bmcl.2016.03.055.
  • Piton, J.; Foo, C. S. Y.; Cole, S. T. Structural Studies of Mycobacterium Tuberculosis DprE1 Interacting with Its Inhibitors. Drug Discov. Today. 2017, 22, 526–533. DOI: 10.1016/j.drudis.2016.09.014.
  • Achutha, L.; Parameshwar, R.; Reddy, B. M.; Babu, V. H. Microwave-Assisted Synthesis of Some Quinoxaline-Incorporated Schiff Bases and Their Biological Evaluation. J. Chem. 2013, 2013, 1–5. DOI: 10.1155/2013/578438.
  • Gulipalli, K. C.; Bodige, S.; Ravula, P.; Bolla, R. S.; Endoori, S.; Cherukumalli, P. K. R.; Seelam, N. V. A Mild and Efficient Copper-Mediated N-Arylation of 6-Azauracil with Corresponding Boronic Acids and Their Antibacterial Activity. Asian J. Chem. 2018, 30, 2495–2501. DOI: 10.14233/ajchem.2018.21491.
  • Ravula, P.; Babu, H.; Manichandrika, P.; Ramanachary, N.; Narendra Sharath Chandra, J. N. Microwave assisted synthesis, biological evaluation and docking studies of novel pyrazoline derivatives as potent antiinflammatory and antibacterial agents. Int. J. Chem. Sci. 2016, 14, 769–782.
  • Bodige, S.; Ravula, P.; Gulipalli, K. C.; Endoori, S.; Narendra Sharath Chandra, J. N.; Cherukumalli, P. K. R.; Vanaja, G. R.; Seelam, N. V. Design, Synthesis and Biological Evaluation of Novel Urea and Thiourea Bearing thieno[3,2-d]-pyrimidines as PI3 Kinase Inhibitors. Anticancer Agents Med. Chem. 2018, 18, 891–902. DOI: 10.2174/1871520618666180209151018.
  • Gulipalli, K. C.; Bodige, S.; Ravula, P.; Endoori, S.; Vanaja, G. R.; Suresh Babu, G.; Narendra Sharath Chandra, J. N.; Seelam, N. V. Design, Synthesis, in Silico and in Vitro Evaluation of Thiophene Derivatives: A Potent Tyrosine Phosphatase 1B Inhibitor and Anticancer Activity. Bioorg. Med. Chem. Lett. 2017, 27, 3558–3564. DOI: 10.1016/j.bmcl.2017.05.047.
  • Ravula, P.; Vamaraju, H. B.; Paturi, M.; Bodige, S.; Gulipalli, K. C.; Narendra Sharath Chandra, J. N. Design, Synthesis, and Docking Studies of Novel Dimethyl Triazene Incorporated Thiazolyl Pyrazolines for Anticancer Activity. J. Heterocycl. Chem. 2018, 55, 1313–1323. DOI: 10.1002/jhet.3163.
  • Ravula, P.; Vamaraju, H. B.; Paturi, M.; Narendra Sharath Chandra, J. N. Design, synthesis, in silico and antiproliferative evaluation of novel pyrazole derivatives as VEGFR‐2 inhibitors. Archiv. Der Pharmazie. 2017, 1–12.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.