Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 24
432
Views
4
CrossRef citations to date
0
Altmetric
Articles

Synthesis of N-substituted dibenzoazepine–pyridazine derivatives as potential neurologically active drugs

ORCID Icon & ORCID Icon
Pages 3845-3853 | Received 28 Aug 2020, Published online: 09 Oct 2020

References

  • Samir, B.; Kalalian, C.; Roth, E.; Salghi, R.; Chakir, A. Gas-Phase UV Absorption Spectra of Pyrazine, Pyrimidine and Pyridazine. Chem. Phys. Lett. 2020, 751, 137469. DOI: 10.1016/j.cplett.2020.137469.
  • Singh, B.; Bhatia, R.; Pani, B.; Gupta, D. Synthesis, Crystal Structures and Biological Evaluation of New Pyridazine Derivatives. J. Mol. Struct. 2020, 1200, 127084. DOI: 10.1016/j.molstruc.2019.127084.
  • Elliott, E.-C.; Regan, S. L.; Maggs, J. L.; Bowkett, E. R.; Parry, L. J.; Williams, D. P.; Park, B. K.; Stachulski, A. V. Haloarene Derivatives of Carbamazepine with Reduced Bioactivation Liabilities: 2-Monohalo and 2,8-Dihalo Derivatives. J. Med. Chem. 2012, 55, 9773–9784. DOI: 10.1021/jm301013n.
  • Datar, P. A. Quantitative Bioanalytical and Analytical Method Development of Dibenzazepine Derivative, Carbamazepine: A Review. J. Pharm. Anal. 2015, 5, 213–222. DOI: 10.1016/j.jpha.2015.02.005.
  • Tian, M.; Abdelrahman, A.; Weinhausen, S.; Hinz, S.; Weyer, S.; Dosa, S.; El-Tayeb, A.; Müller, C. E. Carbamazepine Derivatives with P2X4 Receptor-Blocking Activity. Bioorg. Med. Chem. 2014, 22, 1077–1088. DOI: 10.1016/j.bmc.2013.12.035.
  • Behl, C.; Moosmann, B. Antioxidant Neuroprotection in Alzheimer’s Disease as Preventive and Therapeutic approach. This Article is Part of a Series of Reviews on “Causes and Consequences of Oxidative Stress in Alzheimer’s Disease.” The Full List of Papers May Be Found on the Homepage of the Journal. Free Radic. Biol. Med. 2002, 33, 182–191. DOI: 10.1016/S0891-5849(02)00883-3.
  • Landek, I. O.; Pešić, D.; Merćep, M.; Stanić, B.; Mesić, M. Synthesis and Anti-Inflammatory Activity of 8H-1-Thia-8-Aza-Dibenzo[e,h]Azulenes. J. Heterocycl. Chem. 2011, 48, 856–863. DOI: 10.1002/jhet.605.
  • Kumar, H. V.; Kumar, P.; Rangaswamy, J.; Sindhu, K. U.; Naik, N. 5H-Dibenz[b,f]Azepine Based Pyrazole Sulphonamides: A Privileged Platform for Probing the Antimicrobial and Antioxidative Properties. Eur. J. Chem. 2015, 6, 394–403. DOI: 10.5155/eurjchem.6.4.394-403.1297.
  • Kumar, H. V.; Kumar, C. K.; Naik, N. Synthesis of Novel 3-Chloro-1-(5H-Dibenz[b,f]Azepine-5yl)Propan-1-One Derivatives with Antioxidant Activity. Med. Chem. Res. 2011, 20, 101–108. DOI: 10.1007/s00044-009-9292-7.
  • Singh, H.; Gupta, N.; Kumar, P.; Dubey, S. K.; Sharma, P. K. A New Industrial Process for 10-Methoxyiminostilbene: Key Intermediate for the Synthesis of Oxcarbazepine. Org. Process Res. Dev. 2009, 13, 870–874. DOI: 10.1021/op900127v.
  • Ravinder, B.; Rajeshwar Reddy, S.; Sridhar, M.; Murali Mohan, M.; Srinivas, K.; Panasa Reddy, A.; Bandichhor, R. An Efficient Synthesis for Eslicarbazepine Acetate, Oxcarbazepine, and Carbamazepine. Tetrahedron Lett. 2013, 54, 2841–2844. DOI: 10.1016/j.tetlet.2013.03.089.
  • Bonhôte, P.; Moser, J.-E.; Humphry-Baker, R.; Vlachopoulos, N.; Zakeeruddin, S. M.; Walder, L.; Grätzel, M. Long-Lived Photoinduced Charge Separation and Redox-Type Photochromism on Mesoporous Oxide Films Sensitized by Molecular Dyads. J. Am. Chem. Soc. 1999, 121, 1324–1336. DOI: 10.1021/ja981742j.
  • Belfield, K. D.; Schafer, K. J.; Mourad, W.; Reinhardt, B. A. Synthesis of New Two-Photon Absorbing Fluorene Derivatives via Cu-Mediated Ullmann Condensations. J. Org. Chem. 2000, 65, 4475–4481. DOI: 10.1021/jo991950+.
  • Wermuth, C. G. Are Pyridazines Privileged Structures? Med. Chem. Commun. 2011, 2, 935–941. DOI: 10.1039/C1MD00074H.
  • Flefel, E.; Tantawy, W.; El-Sofany, W.; El-Shahat, M.; El-Sayed, A.; Abd-Elshafy, D. Synthesis of Some New Pyridazine Derivatives for Anti-HAV Evaluation. Molecules. 2017, 22, 148. DOI: 10.3390/molecules22010148.
  • Bindu, B.; Vijayalakshmi, S.; Manikandan, A. Synthesis and Discovery of Triazolo-Pyridazine-6-yl-Substituted Piperazines as Effective Anti-Diabetic Drugs; Evaluated over Dipeptidyl Peptidase-4 Inhibition Mechanism and Insulinotropic Activities. Eur. J. Med. Chem. 2020, 187, 111912. DOI: 10.1016/j.ejmech.2019.111912.
  • Bachollet, S. P. J. T.; Vece, V.; McCracken, A. N.; Finicle, B. T.; Selwan, E.; Ben Romdhane, N.; Dahal, A.; Ramirez, C.; Edinger, A. L.; Hanessian, S. Synthetic Sphingolipids with 1,2-Pyridazine Appendages Improve Antiproliferative Activity in Human Cancer Cell Lines. ACS Med. Chem. Lett. 2020, 11, 686–690. DOI: 10.1021/acsmedchemlett.9b00553.
  • Oliveira, B. L.; Guo, Z.; Bernardes, G. J. L. Inverse Electron Demand Diels-Alder reactions in chemical biology. Chem. Soc. Rev. 2017, 46, 4895–4950. DOI: 10.1039/c7cs00184c.
  • Kocak, R.; Akın, E. T.; Kalın, P.; Talaz, O.; Saracoglu, N.; Dastan, A.; Gülcin, I.; Durdagi, S. Synthesis of Some Novel Norbornene-Fused Pyridazines as Potent Inhibitors of Carbonic Anhydrase and Acetylcholinesterase: Synthesis of Some Novel Norbornene-Fused Pyridazines. J. Heterocyclic Chem. 2016, 53, 2049–2056. DOI: 10.1002/jhet.2558.
  • Erdoğan, M.; Daştan, A. Design, Synthesis, and Characterization of a New Class of Efficient Dihydropyridazine-Dibenzosuberenone Derived Fluorescent Dyes and Investigation of Their Some Photophysical Properties. Tetrahedron. 2020, 76, 131271. DOI: 10.1016/j.tet.2020.131271.
  • Eckardt, R. D.; Jaensch, H.-J. D. Process for the Preparation of 5H-Dibenz[b,f]Azepine-5-Carboxamide. 1994. https://patents.google.com/patent/DE4307181C1/en
  • Shankar, M. K.; Manjunath, B. C.; Vinay Kumar, K. S.; Pampa, K. J.; Sadashiva, M. P.; Lokanath, N. K. Crystal Structure, Spectral Studies, and Hirshfeld Surfaces Analysis of 5-Methyl-5 H -Dibenzo [b, f] Azepine and 5-(4-Methylbenzyl)-5 H -Dibenzo [b, f] Azepine. J. Crystallogr. 2014, 2014, 1–9.
  • Yousuf, S.; Khan, M.; Fazal, S.; Butt, M.; Basha, F. Z. 5-(Prop-2-yn-yl)-5H-dibenzo[b,f]azepine Acta Crystallogr. Sect. E Struct. Rep. Online. 2012, 68, o1101. DOI: 10.1107/S1600536812007866.
  • Kocak, R.; Dastan, A.; Saracoglu, N. Synthesis of Pyridazine and Pyrrole Analogues of 2-Aminotetralin as Potential Dopaminergics. J. Heterocyclic Chem. 2018, 55, 1489–1493. DOI: 10.1002/jhet.3180.
  • Klingele, M. H.; Boyd, P. D. W.; Moubaraki, B.; Murray, K. S.; Brooker, S. Probing the Dinucleating Behaviour of a Bis-Bidentate Ligand: Synthesis and Characterisation of Some Di- and Mononuclear Cobalt(II), Nickel(II), Copper(II) and Zinc(II) Complexes of 3,5-Di(2-Pyridyl)-4-(1H-Pyrrol-1-yl)-4H-1,2,4-Triazole. Eur. J. Inorg. Chem. 2006, 2006, 573–589. DOI: 10.1002/ejic.200500972.
  • Matsuda, T.; Sato, S. Synthesis of Dibenzoheteropines of Group 13-16 Elements via Ring-Closing Metathesis. J. Org. Chem. 2013, 78, 3329–3335. DOI: 10.1021/jo4001993.
  • Abdoh, M. M. M.; Madan Kumar, S.; Vinay Kumar, K. S.; Manjunath, B. C.; Sadashiva, M. P.; Lokanath, N. K. 5-(Prop-2-yn-1-yl)-5H-Dibenzo[b,f]Azepine: Ortho-Rhom-bic Polymorph. Acta Crystallogr. Sect. E Struct. Rep. Online. 2013, 69, 17. DOI: 10.1107/S1600536812048908.
  • Kanase, Y.; Kuniyoshi, M.; Tabata, H.; Takahashi, Y.; Kayama, S.; Wakamatsu, S.; Oshitari, T.; Natsugari, H.; Takahashi, H. Freezing the Butterfly Motion of Carbamazepine Derivatives. Synthesis. 2015, 47, 3907–3913. DOI: 10.1055/s-0035-1560201.
  • Zhang, S.-J.; Ma, Y.-C.; Zhou, W.; Rao, G.-W.; Chen, L.-L.; Hu, W.-X. Synthesis of Esters and Amides of 1,4-Dihydro-1,2,4,5-Tetrazine-3,6-Dicarboxylic Acid. J. Chem. Res. (S). 2009, 2009, 645–648. DOI: 10.3184/030823409X12532880130972.

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.