Review of synthetic strategies in the development of oxadiazine scaffolds

Authors

  • Mohammad Arif Pasha GITAM(DEEMED TO BE UNIVERSITY)
  • Sumanta Mondal GITAM (DEEMED TO BE UNIVERSITY)
  • Naresh Panigrahi GITAm (DEEMED TO BE UNIVERSITY)

DOI:

https://doi.org/10.13171/mjc851907025map

Abstract

Heterocycles containing both oxygen and nitrogen are in a tremendous demand for their immense biological activities. Oxadiazines are the scaffolds shown pleasing activities like antibacterial, antifungal, anthelmintic, anti-inflammatory, locomotor, anticonvulsive, antiviral, antitumor, agricultural, insecticidal, nematocidal, miticidal, neurogenerative disorders like Alzheimer disease, blood disorders like anemia and plant regulation. Multiple syntheses of oxadiazine scaffolds like 1,2,4-oxadiazines, 1,2,5-oxadiazines, 1,3,4-oxadiazines, 1,3,5-oxadiazines have been summarized in the review. Several research chemists are making attempts to discover and introduce the new scaffolds for various diseases ailments in the present scenario. Here we made an attempt to introduce the scaffolds of substituted oxadiazines because a lesser amount of research was carried out on these nuclei.

References

- T. Naito, Development of New Synthetic Reactions for Nitrogen-Containing Compounds and Their Application, Chem. Pharm. Bull.,2008, 56, 1367-1383.

- N. R. Candeias, L. C. Branco, P. M. Gois, C. A. Afonso, A. F. Trindade, more sustainable approaches for the synthesis of N based heterocycles, Chem. Rev.,2009, 109(6), 2703-2802.

- E. Lukevits, M. Shimanska, L. Leibs, I. Lovel, Catalytic synthesis and reactions of nitrogen heterocycles (review), Chem. Heterocycl. Compd., 1994, 30(11-12), 1284-1307.

- T. Cam-Van, W. Jeffrey Bode, Synthesis of Saturated N Heterocycles, J. Org. Chem., 2014, 79, 2809−2815.

- M. Amir, S. A. Javed, K. Harish, Synthesis of some 1, 3, 4-oxadiazole derivatives as potential anti-inflammatory agents, Indian J. Chem., 2007, 46B: 1014-1019.

- O. Lopez, J. G. Fernandez-Bolanos, M. V. Gil, New trends in pest control: the search for greener insecticides, Green Chem., 2005, 7, 431-42.

- D. Xu, X. Cai, S. Gong, Design, Synthesis and Evaluation of Insecticidal Activity of Novel Oxadiazine Derivatives, Curr. Bioact. Compd.,2018, 14, 9-20.

- A. A. Shetnev, F. I. Zubkov, The latest advances in chemistry of 1,2,4-oxadiazines (microreview), Chem. Heterocyl. Comp.,2017, 53(5), 495-497.

- S. Ke, X. Cao, Y. Liang, K. Wang, Z. Yang, Synthesis and biological properties of dihydro-oxadiazine-based heterocyclic derivatives, Mini-Rev. Med. Chem.,2011, 11(8), 642-657.

- H. S. Kim, Y. Kurasawa, Synthesis of 1,3, 4-thiadiazines and 1,3,4-oxadiazines, Heterocycles, 1998, 49(1), 557-586.

- Sultanat, A. Ali, M. Asif, A. Rizvi, M. Farhan, S. Zaman, Discovery of a novel oxadiazine derivative of glucocorticoids endowed with DNA binding activities and molecular docking studies, J. Taibah Univ. Sci., 2019, 13(1), 536-546.

- K. Voracova, J. Hajek, J. Mares, P. Urajova, M. Kuzma, J. Cheel, A. Villunger, A. Kapuscik, M. Bally, P. Nova, M. Kabela, G. Krumschnabel, M. Lukes, L. Voloshko, J. Kopecky, P. Hrouzek, The cyanobacterial metabolite nocuolin A is a natural oxadiazine that triggers apoptosis in human cancer cells, PLoS One, 2017, 12(3), e0172850.

- T. Bergmann, D. Schories, B. Steffan, Alboinon, an oxadiazinone alkaloid from the ascidian Dendrodagrossularia, Tetrahedron, 1997, 53(6), 2055-2060.

- I. T. Kay, I. T. Streeting, A Simple Synthesis of 4-Dimethylamino-2-oxo-2H-1,3,5-oxadiazines, Synthesis,1976, 1, 38.

- K. D. Wing, M. E. Schnee, M. Sacher, Connair, A novel oxadiazine insecticide is bioactivated in lepidopteran larvae, Arch. Insectbiochem. Physiol., 1998, 37, 91-103.

- L. Bruno, F. Grolleau, D. B. Sattelle, Indoxcarb an oxadiazine insecticide, blocks insect neuronal sodium channels, Br. J. Pharmacol., 2001, 132(2), 587-595.

- D. Xu, J. Guan, X. Xu, S. Gong, H. Xu, A New Method for the Synthesis of Oxadiazine Insecticide Indoxacarb, J. Heterocyl. Chem.,2016, 53, 1469-1473.

- P. Rajagopalan, C. N. Talaty, A New synthesis of 1,2,4-oxadiazine derivatives from 1-aroylaziridine oximes, J. Am. Chem. Soc., 1966, 88(21), 5048-5049.

- M. A. Calcagno, H. W. Heine, C. Kruse, W. A. Kofke, The synthesis and reactions of 4-aroyltetrahydro-2H-1,2,4-oxadiazines, J. Org. Chem., 1974, 39(2), 162-166.

- Z.-Y. Sun, T. Asberom, T. Bara, C. Bennett, D. Burnett, I, Chu, J. Clader, C.-W. Mary, D. Cole, M.Czarniecki, J. Durkin, G. Gallo, W. Greenlee, H. Josien, X. Huang, L. Hyde, N.Jones, I. Kazakevich, H. Li, X. Liu, J. lee, M. MacCoss, M. B. Mandal, T. McCracken, A. Nomeir, R. Mazzola, A. Palani, E. M. Parker, D. A. Pissarnitski, JunQin, L. Song, G. Terracina, M. Vicarel, J. Voigt, R. Xu, L. Zhang, Q. Zhang, Z. Zhao, X. Zhu, Z. J. Zhu, Cyclic Hydroxyamidines as Amide Isosteres: Discovery of Oxadiazolines and oxadiazines as potent and highly efficacious γ-Secretase modulators in vivo, Med. Chem., 2012, 55, 489-502.

- X. Huang, W. Zhou, X. Liu, H. Li, G. Sun, M. Mandal, M. Vicarel, X. Zhu, C. Bennett, T. McCraken, D. Pissarnitski, Z. Zhao, D. Cole, G. Gallo, Z. Zhu, A. Palani, R. Aslanian, J. Clader, M. Czarniecki, W. Greenlee, D. Burnett, M. Cohen-Williams, L. Hyde, L. Songs, L. Zhang, I. Chu, A. Buevich, Synthesis and SAR studies of fused oxadiazines as γ-Secretase modulators for the treatment of Alzheimer’s Disease, Med. Chem. Lett., 2012, 3, 931-935.

- S. R. Pathipati, V. Singh, L. Eriksson, N. Selander, Lewis acid catalyzed Annulation of nitrones with oxiranes, aziridines and Thiiranes, Org. Lett., 2015, 17(18), 4506-4509.

- S. P. Miller, W. J. Morris, R. K. Orr, J. Eckert, J. Milan, M. Maust, C. Cowden, J. Cui, Synthesis of the γ-Secretase Modulator MK-8428, J. Org. Chem., 2017, 82(6), 2957-2964.

- X. Li, Z. Zhang, W. Wei, H. Chang, W. Gao, CN Patent 105 461 651.

- A. Yuanyuan, X. Hongguang, W. Jie, Base-controlled [3+3] cycloaddition of isoquinoline N-oxides with azaoxyallyl cations, Chem. Commun., 2016, 52, 10415-10418.

- L.-B. Zhang, X.-Q. Hao, Z.-J. Liu, X.X. Zheng, S.-K. Zhang, J.-L. Niu, M.-P. Song, Cobalt(II) catalysed Csp2-H Alkynylation/Annulation with terminal alkynes: Selective access to 3-methyleneisoindolin-1-one, Angew. Chem. Int. Ed., 2015, 54(34), 10012-10015.

- S. Crotti, F. Berti, M. Pineschi, Copper-Catalyzed perkin-Acyl-Mannich reaction of acetic anhydride with pyridine: Expeditious entry to unconventional piperidines, Org. Lett., 2011, 13(19), 5152-5155.

- A. F. Trindade, J. W. Bode, Irreversible conjugation of aldehydes in water to form stable 1,2,4-oxadiazinan-5-ones, Org. Lett., 2016, 18(17), 4210-4213.

- H. Y. Song, Y. L. Cho, D. Y. Lee, H. S. Park, S. Y. Baek, S. E. Chae, S. H. Jo, Y. O. Kim, H. S. Lee, J. H. Park, T. K. Park, S. H. Woo, Y. Z. Kim, US Patent 20110112083.

- W. Gangqiang, R. Chen, S. Zhao, L. Yang, H. Guo, S. Sun, J. Wang, J. Domena, Y. Xing, Efficient synthesis of 1,2,4-oxadiazine-5-ones via [3+3] cycloaddition of in situ generated aza-oxyallylic cations with nitrile oxides, Tetrahedron Lett., 2018, 59(21), 2018-2020.

- A. Mustafa, W. Asker, A.H. Hurhash, M. A. E. Khalifa, E. M. Zayed, The behavior of oxazoline-(5) and thiazolinone-(5) against N-Phenyl hydroxylamine and Phenylhydrazine, Liebigs Ann. Chem., 1968, 713, 151-161.

- M. Barbar, S. Kraljevi, M. Grce, B. Zorc, Novel 1,2,5-oxadiazine Derivatives-Synthesis and Invitro Biological studies, Acta Pharm, 2003, 53, 175-186.

- E. A. Chugunovaa, N. I. Akylbekovb, N. V. Gavrilovb, V.A. Samsonovc, S. A. Sitnovd, A. B. Dobrynina, M. A. Pudovika, A. R. Burilova, Synthesis of new 3H-benzo[1,2,5]oxadiazine-4-oxide, Russ. J. Gen. Chem., 2016, 86(11), 2548-2550.

- R. M. Mohareb, R. A. Ibrahim, H. E. Moustafa, Hydrazide-hydrazones in the synthesis of 1,3,4-oxadiazine, 1,2,4- Triazine and pyrazole derivatives with antitumor activities, Open Org. Chem., J., 2010, 4(2), 08-14.

- R. M. Mohareb, A. A. El-Khair, Novel synthesis of hydrazide-hydrazone and their uses for the synthesis 1,3,4-oxadiazine, 1,2,4-triazine, pyrazole and pyridazine derivatives with antimicrobial and antifungal activities, Int. J Appl. Biol. Pharm.,2011, 2, 434-446.

- M. L. Tintas, A. P. Diac, A. S. A. Terec, I. Grosu, E. Bogdan, Structural Characterization of new 2-aryl 5-phenyl-1,3,4-oxadiazin-6-ones and their N-aroylhydrazone precursors, J. Mol. Struct., 2014, 1058, 106-113.

- V. Thirupathaiah, K. Suhasini, T. V. Padmanabha Rao, Synthesis of 2, 6-diaryl-4H-1,3,4-oxadiazines as antibacterial agents, Curr. Sci., 1983, 52, 1133-1135.

- K. Srinivas, T. Soujanya, Synthesis of some new 1,3,4 oxadiazine-[6,5-b] indole derivatives and their biological activity, Afr. J. Pharm Pharmacol., 2014, 8(25), 701-705.

- N. N. Karade, J. M. Kondre, S. V. Gampawar, S. V. Shinde, Synthesis of 2,5-disubstituted 1,3,4-oxadiazine and 1,3,4-thiadiazine from substituted acetophenones and acid hydrazides using [Hydroxyl(tosyloxy)iodo] benzene, Synth. Commun., 2009, 39, 2279-2287.

- Q. Yang, S.-Y. Ke, X.-H. Qian, F.-Y. Liu, Z. Li, Novel 4H-1,3,4-oxadiazin-5(6H)-ones with hydrophobic and long alkyl chains: design, synthesis and bioactive diversity on inhibition of monoamine oxidase, chitin biosynthesis and tumor cell, Eur. J. Med. Chem., 2009, 44, 2113-2121.

- S. Samshuddin, J. P. Jasinski, J. A. Golen, B. Narayana, H. S. Yathirajan, C. Glidewell, Hydrogen-bonded chains in 3,5-bis(4-fluorophenyl)-1- phenyl-1H-pyrazole and complex hydrogen-bonded sheets in (5RS,6SR)-6-(4-fluorobenzoyl)-5-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5,6-dihydro 4H-1,3,4-oxadiazine

N,N-dimethylformamidemonosolvate, Acta Cryst., 2014, C70 (9), 867-871.

- K. Shubakara, K. B. Umesha, N. Srikantamurthy, J.Chethan, Antioxidant and DNA damage inhibition activities of 4-aryl-N-(4-aryl-thiazol-2-yl)-5,6-dihydro-4H-1,3,4-oxadiazine-2-carboxamides, J. Chem. Sci., 2014, 126(6), 1913-1921.

- V. F. Vavsari, G. M. Ziarani, S. Balalaie, A. Badiei, F. G. Mohammadi, S. Ramezanpour, F. Rominger, Unexpected synthesis of 1,3,4-oxadiazines using extraordinary effect of SBA-Pr-SO3H as a nano catalyst. Chemistry Select, 2017, 2, 3496-3499.

- M. Bakavoli, M. Rahimizadeh, A. Shiri, H. Eshghi, S. Vaziri-Mehr, P. Pordeli, M. Nikpour, Synthesis and evaluation of antibacterial activity of new derivatives of pyrimido[4,5-e][1,3,4]oxadiazine, Heterocycl. Commun., 2011,17, 49-52.

- M. Bakavoli, M. Rahimizadeh, A. Shiri, H. Eshghi, P. Pordeli, M. Pordel, M. Nikpour, Synthesis and antibacterial Evaluations of new pyridazino[4,3-e][1,3,4]oxadiazines, J. Heterocycl. Chem., 2011, 48, 149-152.

- K. M. Khan, S. Rahat, M. I. Choudhary, Atta-ur-Rahman, U. Ghani, S. Perveen, S. Khatoon, A. Dar, A. Malik, Synthesis and biological screening of 2-substituted 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4- propanenitriles and of their intermediates, Helv.Chim. Acta, 2002, 85, 559-570.

- Q. Zhang, L.-G. Meng, J. Zhang, L. Wang, DMAP-catalyzed [2+4]cycloadditions of allenoates with N-Acyldiazines: Direct method to 1,3,4-oxadiazine derivatives, Org. Lett., 2015, 17(13), 3272-3275.

- F. M. Eissa, A. R. Abdelghany, New 1,3,4-oxadiazinoisoquinoline methane cyanine dyes: Synthesis photosensitivity and antibacterial activity, J. Heterocycl. Chem., 2016, 53(2), 429-436.

- M. A. Dekeyser, W. A. Harrison, P. T. McDonald, G. W. Angle, Jr. S. M. M. Ismail, R. G. H. Downer, Computer-Aided Molecular Design; C. H. Reynolds, M. K. Holloway, K. Harold Cox, ed. ACS Symposium series, American chemical society, 1995, 589, 183-195.

- M. A. Dekeyser, W. A. Harrison, P. T. McDonald, R. G. H. Downer, Design and Synthesis of 5,6-dihydro-4H-1,3,4-oxadiazines as potential octopaminergic insecticides, Pestic. Sci., 1993, 38, 309-314.

- A. J. Elliott, Hydrazides and Thiohydrazides as sources of condensed oxadiazines and Thiadiazines, including novel azo derivatives based on dithizone, J. Org. Chem.,1980, 45, 3677-3681.

- Eissa, M. Fayez, Green Synthesis, Antibacterial, and Antifungal Activities of 1,3,4-Oxadiazines, J. Heterocycl. Chem., 2018, 55(6), 1479-1483.

- F. W. Hoover, H. B. Stevensoannd, H. S. Rothrock, Chemistry of isocyanic acid. I. Reactions of isocyanic acid with carbonyl compounds, J. Org. Chem., 1963, 28(7), 1825-1830.

- L. A. McGrew, W. Sweeny, T. W. Campbell, V. S. Foldi, Reaction of Benzoyl isocyanate with a phospholene oxide catalyst, J. Org. Chem., 1964, 29(10), 3002-3004.

- M. E. Hermes, R. A. Braun, Oxadiazines and dioxazines from perhaloacetones and cyanamides, J. Org. Chem., 1966, 31(8), 2568-2571.

- O. Tsuge, M. Tashiro, R. Mizuguchi, S. Kanemasa, Dipolar cycloadditions reaction of benzoyl and thiobenzoyl isocyanates, Chem. Pharm. Bull., 1966, 14(9), 1055-1057.

- H. S. Patel, K. B. Patel, Synthesis and biological activity of 3-[4H-(1,2,4)-Triazolyl]-2,6-diaryl-1,3,5-oxadiazine-4-thione, Phosphorous, sulfur Silicon Relat. Elem., 2009, 184(9), 2443-2452.

- K. H. Patel, A. G. Mehta, Synthesis and antifungal activity of [(4-(2-naphthalenyl) thiazol-2-yl)-2-(substituted phenyl)-6-phenyl-4-thioxo-1,3,5-oxadiazine] derivatives, Der Chemica Sinica, 2012, 3(6), 1410- 1414.

- N. Rambabu, D. Ramachandran, B. M. Viral, J. G. Kirti, Synthesis, characterization and biological evaluation of 2,6-diphenyl-3-(4-(3-phenyl-[1,2,4,]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)phenyl)-2H-1,3,5-oxadiazine-4(3H)-thione, Der Pharma Chemica, 2012, 4(2), 639-643.

- N. Rambabu, B. M. Viral, J. G. Kirti, Synthesis, characterization and biological evaluation of 2,6-diphenyl- 3-(4-(3-phenyl-[1,2,4,]triazolo[3,4-b] [1,3,4]thiadiazol-6-yl)phenyl)-2H-1,3,5-oxadiazine-4(3H)-thione, Der Pharma Chemica, 2012, 4(1), 511-516.

- S. K. Younis, B. A. Ahmed, Synthesis of some new 1,3,5-oxadiazine derivatives, Raf. Jour. Sci., 2008, 19(3), 10-17.

- V. Z. Pavlo, V. K. Vadym, O. P. Ihor, V. K. Aleksandr, A new method for the synthesis of 4H-1,3,5-oxadiazine derivatives, Heterocycl. Commun.,2017, 23(5), 369-374.

Downloads

Published

2019-07-02

Issue

Vol. 8 No. 5 (2019)

Section

Medicinal Chemistry

License

Authors who publish with this journal agree to the following terms:

    1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal
    2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal
    3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).