Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 21
229
Views
7
CrossRef citations to date
0
Altmetric
Synthetic Communications Reviews

N'-(1-([1,1'-biphenyl]-4-yl)ethylidene)-2-cyanoacetohydrazide as scaffold for the synthesis of diverse heterocyclic compounds as prospective antitumor and antimicrobial activities

, , ORCID Icon &
Pages 3017-3029 | Received 14 May 2019, Published online: 27 Aug 2019

References

  • Jain, Z. J.; Gide, P. S.; Kankate, R. S. Biphenyls and Their Derivatives as Synthetically and Pharmacologically Important Aromatic Structural Moieties. Arab. J. Chem. 2017, 10, s2051–s2066. DOI: 10.1016/j.arabjc.2013.07.035.
  • Sharma, A.; Chakravarti, B.; Gupt, M. P.; Siddiqui, J. A.; Konwar, R.; Tripathi, R. P. Synthesis and Anti-Breast Cancer Activity of Biphenyl Based Chalcones. Bioorg. Med. Chem. 2010, 18, 4711–4720. DOI: 10.1016/j.bmc.2010.05.015.
  • Makarov, V. A.; Riabova, O. B.; Granik, V. G.; Wutzler, P.; Schmidtke, M. Novel [(Biphenyloxy)Propyl]Isoxazole Derivatives for Inhibition of Human Rhinovirus 2 and Coxsackievirus B3 Replication. J. Antimicrob. Chemother. 2005, 55, 483–488. DOI: 10.1093/jac/dki055.
  • Jaina, A.; Ratnawata, S.; Chaturvedib, S. C. Rationalization of Physicochemical and Structural Requirement of Some Substituted 5-(Biphenyl-4-Ylmethyl)Pyrazole as Angiotensin II Receptor Antagonist: A QSAR Approach. Iran. J. Pharm. Sci. 2010, 6, 51–58.
  • Sharma, M. C.; Kohlia, D. V.; Sharma, S.; Sharma, A. D. Design, Synthesis, and Pharmacological Evaluation of 4'-{2-[4-[3chloro-2-(Substituted-Phenyl)-4-Oxo-Azetidin-1-yl)-Phenyl]Benzoimidazol-1-Ylmethyl}-Biphenyl-2-Carboxylic Acids. Der. Pharma. Sinic. 2010, 1, 82–94.
  • Shah, U. A.; Wagh, N. K.; Deokar, H. S.; Kadam, S. S.; Kulkarni, V. M. 3d-QSAR of Biphenyl Analogues as Anti-Inflammatory Agents by Genetic Function Approximation (GFA) (Part-II. ). Int. J. Pharm. Bio. Sci. 2010, 1, 512–522.
  • Ding, Y.; Mao, L.; Xu, D.; Xie, H.; Yang, L.; Xu, H.; Geng, W.; Gao, Y.; Xia, C.; Zhang, X.; et al. C-Aryl Glucoside SGLT2 Inhibitors Containing a Biphenyl Motif as Potential Anti-Diabetic Agents. Bioorg. Med. Chem. Lett. 2015, 25, 2744–2748. DOI: 10.1016/j.bmcl.2015.05.040.
  • Sachan, N.; Thareja, S.; Agarwal, R.; Kadam, S. S.; Kulkarni, V. M. Substituted Biphenyl Ethanones as Antidiabetic Agents: synthesis and In-Vivo Screening. Int. J. Pharm. Tech. Res. 2009, 1, 1625–1631.
  • Meti, G. Y.; Kamble, R. R.; Kamble, A. A.; Kumbar, M. N.; Joshi, S. D.; Dixit, S. R. Synthesis and Anti-Proliferative Activity of Biphenyl Derived 5-Substituted-Indolin 2-Ones. Arch. Chem. Res. 2016, 1, 1. DOI: 10.21767/2572-4657.100004.
  • Galici, R.; Jones, C. K.; Hemstapat, K.; Nong, Y.; Echemendia, N. G.; Williams, L. C.; Paulis, T. d.; Conn, P. J. Biphenyl-Indanone A, a Positive Allosteric Modulator of the Metabotropic Glutamate Receptor Subtype 2, Has Antipsychotic- and Anxiolytic-like Effects in Mice. J. Pharm. Exp. Ther. 2006, 318, 173–185. DOI: 10.1124/jpet.106.102046.
  • Yar, M. S.; Ansari, Z. H. Synthesis and In Vivo Diuretic Activity of Biphenyl Benzothiazole-2-Carboxamide Derivatives. Acta Pol. Pharm. Drug Res. 2009, 66, 387–392.
  • Akkala, M.; Kannappan, N.; Aakashdeep, Kumar, P.; Kumar, M.; Verma, P. Synthesis and Antimicrobial Studies of Biphenyl-4-Carboxylic Acid 2-(Aryl)-4-Oxo-Thiazolidin-3-yl-Amide. Int. J. Chem. Tech. Res. 2009, 1, 1376–1380.
  • Wurl, O.; Obbard, J. P. Organochlorine Pesticides, Polychlorinated Biphenyls and Polybrominated Diphenyl Ethers in Singapore’s Coastal Marine Sediments. Chemosphere 2005, 58, 925–933. DOI: 10.1016/j.chemosphere.2004.09.054.
  • Sajwan, K. S.; Kumar, K. S.; Nune, S.; Fowler, A.; Richardson, J. P.; Loganathan, B. G. Persistent Organochlorine Pesticides, Polychlorinated Biphenyls, Polybrominated Diphenyl Ethers in Fish from Coastal Waters off Savannah, GA, USA. Toxicol. Environ. Chem. 2008, 90, 81–96. DOI: 10.1080/02772240701270047.
  • Ismail, M. F.; El-Sayed, A. A. Synthesis and In-Vitro Antioxidant and Antitumor Evaluation of Novel Pyrazole-Based Heterocycles. J. Iran. Chem. Soc. 2019, 16, 921–937. DOI: 10.1007/s13738-018-1566-x.
  • Ismail, M. F.; El-Sayed, G. A. Dodecanoyl Isothiocyanate and N’-(2-Cyanoacetyl)Dodecanehydrazide as Precursors for the Synthesis of Different Heterocyclic Compounds with Interesting Antioxidant and Antitumor Activity. Synth. Commun. 2018, 48, 892–905. DOI: 10.1080/00397911.2018.1428345.
  • Mahmoud, M. R.; Shiba, S. A.; El-Ziaty, A. K.; Abu El-Azm, F. S. M.; Ismail, M. F. Synthesis and Reactions of Novel 2,5-Disubstituted 1,3,4-Thiadiazoles. Synth. Commun. 2014, 44, 1094–1102. DOI: 10.1080/00397911.2013.846381.
  • Mahmoud, M. R.; El-Ziaty, A. K.; Abu El-Azm, F. S. M.; Ismail, M. F.; Shiba, S. A. Utility of Cyano-N-(2-Oxo-1,2-Dihydroindol-3-Ylidene)Acetohydrazide in the Synthesis of Novel Heterocycles. J. Chem. Res. 2013, 37, 80–85. DOI: 10.3184/174751912X13567100793191.
  • Buu-Hoi, N. P.; Royer, R. Friedel-Crafts Reactions with 4-Alkylbiphenyls and 4-Benzylbiphenyl. Recl. Trav. Chim. Pays-Bas. 1951, 70, 825–832. DOI: 10.1002/recl.19510700909.
  • Mohareb, R. M.; El-Sayed, N. N. E.; Abdelaziz, M. A. Uses of Cyanoacetylhydrazine in Heterocyclic Synthesis: Novel Synthesis of Pyrazole Derivatives with Anti-Tumor Activities. Molecules 2012, 17, 8449–8463. DOI: 10.3390/molecules17078449.
  • El-Semary, M. M. A. Novel Pyrrolidine-2,5-Diones and Thiazolidine-2,4-Diones as Potential Anticonvulsant Agents. Alex. J. Pharm. Sci. 2007, 21, 59–63.
  • Suryakiran, N.; Ramesh, D.; Venkateswarlu, Y. Synthesis of 3-Amino 1H-Pyrazoles Catalyzed by p-Toluene Sulphonic Acid Using Polyethylene Glycol-400 as an Efficient and Recyclable Reaction Medium. Green Chem. Lett. Rev. 2007, 1, 73–78. DOI: 10.1080/17518250701771909.
  • Larry, T. P.; Michael, M. C.; Florence, O. M. Synthesis of Novel 3,4-Diaryl-5-Aminopyrazoles as Potential Kinase Inhibitors. Tetrahedron 2011, 67, 4601–4611. DOI: 10.1016/j.tet.2011.04.077.
  • Ingersoll, A. W.; White, E. G. Solubility Relationships among Optically Isomeric Salts. I. Malates of α-p-Xenylethylamine. J. Am. Chem. Soc. 1932, 54, 274–281. DOI: 10.1021/ja01340a041.
  • Takase, A.; Murabayashi, A.; Sumimoto, S.; Ueda, S.; Makisumi, Y. Practical Synthesis of 3-Amino-5-Tert-Butylisoxazole from 4,4-Dimethyl-3-Oxopentanenitrile with Hydroxylamine. Heterocycles 1991, 32, 1153–1158. DOI: 10.3987/COM-91-5712.
  • Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival: application to Proliferation and Cytotoxicity Assays. J. Immunol. Meth. 1983, 65, 55–63. DOI: 10.1016/0022-1759(83)90303-4.
  • Denizot, F.; Lang, R. Rapid Colorimetric Assay for Cell Growth and Survival. Modifications to the Tetrazolium Dye Procedure Giving Improved Sensitivity and Reliability. J. Immunol. Meth. 1986, 89, 271–277. DOI: 10.1016/0022-1759(86)90368-6.
  • Hossain, M. A.; Shah, M. D.; Sang, S. V.; Sakari, M. Chemical Composition and Antibacterial Properties of the Essential Oils and Crude Extracts of Merremia borneensis. J. King Saud Univ. Sci. 2012, 24, 243–249. DOI: 10.1016/j.jksus.2011.03.006.
  • Alam, M. T.; Karim, M. M.; Khan, S. N. Antibacterial Activity of Different Organic Extracts of Achyranthes aspera and Cassia alata. J. Sci. Res. 2009, 1, 393–398. DOI: 10.3329/jsr.v1i2.2298.

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.