Click Here

Details



REVIEW ON (AZO, FORMAZANE, SULFAZANE)-COMPOUNDS

Dr. Nagham Mahmood Aljamali

18-44

Vol. 10, Jul-Dec, 2019

Date of Submission: 2019-07-02 Date of Acceptance: 2019-08-08 Date of Publication: 2019-08-14

Abstract

Azo compounds represent the essential compound of organic reactions and the basic material for preparing many ligands, complexes, dyes, polymers, antioxidants, bioactive compounds and other biological compounds., this review involves azo compounds with its derivatives (Formazane and Sulfazane), also in this review ,we explained sulfazane as first time in first review about this compound as a new reaction fordiazo salt that prepared for the first time by (Dr. Nagham in year 2019) via many studies in this field.

References

  1. Nagham Mahmood Aljamali, (2015). Review in Azo Compounds and its Biological Activity. Biochem Anal Biochem ,4, 169., doi:10.4172/2161-1009.1000169.
  2. Nagham Mahmood Aljamali . 2014. Synthesis and Investigation of Formazane compounds (Azo– Imine) and their complexes, Asian J. Research Chem, 7 (2), 225-231.
  3. Fei, Na; Sauter, Basilius; Gillingham, Dennis (2016). 'The pK a of Brønsted acids controls their reactivity with diazo compounds'. Chemical Communications. 52(47): 7501–7504. doi:10.1039/C6CC03561B.
  4. Nagham Mahmood Aljamali, Dhuha RahiK .(2017). New Formazan Compounds (Synthesis, Identification, Physical Properties)., Journal of Chemical and Pharmaceutical Sciences., 10(3) ,1-16.
  5. Nagham Mahmood Aljamali, Alia Jawd Kadheum, Jelel Hassain Mohemd, Rajaa Abdulameer Ghafil. Review on Preparation and Applications of Formazan Compounds. International Journal ofThermodynamics and Chemical Kinetics. 2019; 5(2): 23–33p.
  6. D. Bravo-Díaz, Carlos (2010), 'Diazohydroxides, Diazoethers and Related Species', in Rappoport, Zvi (ed.), PATai's Chemistry of Functional Groups, John Wiley & Sons, Ltd, doi:10.1002/9780470682531.pat0511, ISBN 9780470682531
  7. Carey, Francis A., (2007). Advanced organic chemistry. Sundberg, Richard J. (5th ed.). New York: Springer. ISBN 9780387448978. OCLC 154040953
  8. Streitwieser, Andrew; Schaeffer, William D. (1957). 'Stereochemistry of the Primary Carbon. VI. The Reaction of Optically Active 1-Aminobutane-1-d with Nitrous Acid. Mechanism of the Amine-Nitrous Acid Reaction1'. Journal of the American Chemical Society. 79 (11): 2888–2893. doi:10.1021/ja01568a054
  9. Friedman, Lester; Jurewicz, Anthony T.; Bayless, John H. (1969). 'Influence of solvent on diazoalkane-alkyldiazonium ion equilibriums in amine deaminations'. Journal of the American Chemical Society. 91 (7): 1795–1799. doi:10.1021/ja01035a032
  10. Norman, R. O. C. (Richard Oswald Chandler) (2017). Principles of Organic Synthesis (3rd ed.). CRC Press. ISBN 9780203742068. OCLC 1032029494.
  11. Chemistry of the Diazonium and Diazo Groups: Part 1. S. Patai, Ed. 1978 Wiley-Blackwell. ISBN 0-471-99492-8. Chemistry of the Diazonium and Diazo Groups: Part 2. S. Patai, Ed. 1978 Wiley-Blackwell. ISBN 0-471-99493-6.
  12. Nagham Mahmood Aljamali, Alaa A H, Intisar Obaid Alfatlawi. Review on Organic Ligands with Their Various Applications. International Journal Lett. 2004;14:6057–6059.
  13. Al-Soud YA, Al-Dweri MN, Al-Masoudi NA. Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivatives. Farmaco. 2004;59:775–783. doi: 10.1016/j.farmac.2004.05.006
  14. Mieaad M, Nagham Mahmood Aljamali ,Wassan Ala Shubber., Sabreen Ali Abdalrahman .'New Azomethine- Azo Heterocyclic of Chem-informatics Research. 2019; 5(1) 41–53p
  15. Filimonov, Victor D.; Trusova, Marina; Postnikov, Pavel; Krasnokutskaya, Elena A.; Lee, Young Min; Hwang, Ho Yun; Kim, Hyunuk; Chi, Ki-Whan (2008). 'Unusually Stable, Versatile, and Pure ArenediazoniumTosylates: Their Preparation, Structures, and Synthetic Applicability'. Organic Letters. 10 (18): 3961–3964
  16. 'UK CRHF Incident Report – Supersaturated Diazonium salt causes Fatality'. UK Chemical Reaction Hazards Forum. Archived from the original on 6 October 2018. Retrieved 13 May 2010
  17. Peter W. Atkins, Julio de Paula: PhysikalischeChemie.,Auflage, Wiley-VCH, Weinheim 2006, ISBN 978-3-527-31546-8, S. 106–108
  18. Almasirad A, Tabatabai SA, Faizi M, Kebriaeezadeh A, Mehrabi N, Dalvandi A, Shafiee A. Synthesis and anticonvulsant activity of new 2-substituted-5-[2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles. Bioorg Med Chem
  19. Ligands Via Cyclization of Ester'.,Research Journal of Pharmacy and Technology , .2018, 11,6 . 2555- 2560 ., DOI : 10.5958/0974-360X.2018.00472.9
  20. Bailey EM, Krakovsky DJ, Rybak M. The triazole antifungal agents: a review of itraconazole and fluconazole. Pharmacotherapy. 1990;10:146–153.
  21. Bourgeois I, Pestel-Caron M, Lemeland JF, Pons JL, Caron F. Tolerance to the glycopeptidesvancomycin and teicoplanin in coagulase-negative Staphylococci. Antimicrob Agents Chemother. 2007;51(2):740–743.
  22. Nagham Mahmood Aljamali.; Intisar Obaid Alfatlawi. 'Synthesis of Sulfur Heterocyclic Compounds and Study of Expected Biological Activity', Research J. Pharm. and Tech., 2015, 8,9 ,1225-1242 , DOI: 10.5958/0974-360X.2015.00224.3.
  23. Clemons M, Coleman RE, Verma S. Cancer Treat Rev. 2004;30:325–332. doi: 10.1016/j.ctrv .2004.03. 004.
  24. Nagham Mahmood Aljamali. (2018).'Review :General Principles in Chemistry'., Ch. 5 ., pages: 60- 91. , ISBN: 978-93-87905-41-2
  25. CLSI (2008) Performance standards for antimicrobial susceptibility testing; Eighteenth International Supplement. CLSI document M7-MIC. Clinical Laboratory Standards Institute, Wayne.
  26. Afaeqgaber Kadem , Ahmed Adnan Abdul Hussein, Nagham Mahmood Aljamali ,Ahmed A A H , Afaq J K. (2020)., Invention of Imidazole &Thiazole-Sulfazane Ligands (Synthesis, Spectral Investigation, Microbial Behavior) for The First Time., Int. J. Pharm. Res., Vol. 12
  27. Afaeqgaber Kadem , Ahmed Adnan Abdul Hussein, Nagham Mahmood Aljamali ,Ahmed A A H , Afaq J K. (2020)., Invention of Imidazole &Thiazole-Sulfazane Ligands (Synthesis, Spectral Investigation, Microbial Behavior) for The First Time., Int. J. Pharm. Res., Vol. 12
  28. Nagham Mahmood Aljamali. 'Reactions and Mechanisms'.,1 Edt., IJMRA Publication ,2018 .,ISBN : 978- 93-87176-25-6
  29. Nagham Mahmood Aljamali . 'Experimental Methods for Preparation of Mannich Bases,Formazan, Normal and Cyclic Sulfur Compounds', 1st edition Evince pub Publishing House;2018, ISBN: 978-93-87905-19-1.
  30. Metwally N.H. A simple green synthesis of (Z)-5-arylmethylene-4-thioxothiazolidines and thiopyrano[2,3-d]thiazolidine-2-thiones in PEG-400 under catalyst-free conditions. J. Sulfur Chem. 2014;35:528–537
  31. Lozynskyi A., Zimenkovsky B., Lesyk R. Synthesis and Anticancer Activity of New Thiopyrano[2,3-d]thiazoles Based on Cinnamic Acid Amides. Sci. Pharm. 2014;82:723–733. doi: 10.3797/ scipharm.1408-05
  32. Lozynskyi A., Zasidko V., Atamanyuk D., Kaminskyy D., Derkach H., Karpenko O., Ogurtsov V., Kutsyk R., Lesyk R. Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids. Mol. Divers. 2017;21:427–436. doi: 10.1007/s11030-017-9737-8.
  33. Lozynskyi A., Zimenkovsky B., Nektegayev I., Lesyk R. Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds. Heterocycl. Commun . 2015;21:55–59. doi: 10.1515/hc-2014-0204
  34. Imad Kareem AlwanAlsabri, HasaneenKudhairAbdullabass ,NaghamMahmoodAljamali, Imad K A A, Hasaneen K A., Invention of (Gluta.Sulfazane-Cefixime) Compounds as Inhibitors of Cancerous Tumors., Journal of Cardiovascular Disease Research, 2020,11, 2., 44-55 ., DOI: 10.31838/jcdr.2020.11.02.09
  35. Aseel Mahmood Jawad, Nagham Mahmood Aljamali, Saher Mahmood Jwad, Aseel M J, Saher M J., Development and Preparation of ciprofloxacin Drug Derivatives for Treatment of Microbial Contamination in Hospitals and Environment, Indian Journal of Forensic Medicine & Toxicology,2020,14, 2, p:1115-1122
  36. Aseel Mahmood Jawad, Nagham Mahmood Aljamali, Saher Mahmood Jwad, Aseel M J, Saher M J., Development and Preparation of ciprofloxacin Drug Derivatives for Treatment of Microbial Contamination in Hospitals and Environment, Indian Journal of Forensic Medicine & Toxicology,2020,14, 2, p:1115-1122
  37. Demirbas A, Sahin D, Demirbas N, Karaoglu SA. Synthesis of some new 1,3,4-thiadiazol-2-ylmethyl-1,2,4-triazole derivatives and investigation of their antimicrobial activities. Eur J Med Chem. 2009;44:2896–2903. doi: 10.1016/j .ejmech.2008.12.005.
  38. Dobosz M, Pachuta-Stec A. Cyclization of 1-cyanoacetyl-4-substituted thiosemicarbazides to 1,2,4-triazole or 1,3,4-thiadiazole derivatives. Acta Pol Pharm. 1995;52:103–111.
  39. Dobosz M, Pachuta-Stec A. Cyclization of 1-cyanoacetyl-4-substituted thiosemicarbazides to 1,2,4-triazole or 1,3,4-thiadiazole derivatives. Acta Pol Pharm. 1995;52:103–111.
  40. Nagham Mahmood Aljamali, Imad Kareem Alwan Alsabri., Development of Trimethoprim Drug and Innovation of Sulfazane-Trimethoprim Derivatives as Anticancer Agents ., Biomedical & Pharmacology Journal, March 2020., Vol. 13, (2), p. 613-625 ., http://dx.doi.org/10.13005/bpj/1925
  41. Dobosz M, Pitucha M, Wujec M. The reactions of cyclization of thiosemicarbazide derivatives to 1,2,4-triazole or 1,3,4-thiadiazole system. Acta Pol Pharm. 1996;53:31–38
  42. Dogan HN, Duran A, Rollas S, Sener G, Uysal MK, Gülen D. Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimicrobial activities. Bioorg Med Chem. 2002;10:2893–2898. doi: 10.1016/S0968-0896(02)00143-8.
  43. Nagham Mahmood Aljamali .,'(Synthesis ,Investigation ,Chromatography ,Thermal)-Behavior of (Five ,Seven)- Membered Ring with Azo and Anil Compounds'.,Pak. J. Biotechnol. Vol. 15 ,1, 219-239 , (2018)
  44. Metwally N.H. Synthesis of some new fused thiopyrano[2,3-d]thiazoles and their derivatives. J. Sulfur Chem. 2007;28:275–284. doi: 10.1080/17415990701299468
  45. Duran A, Dogan HN, Rollas S. Synthesis and preliminary anticancer activity of new 1,4-dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-5H-1,2,4-triazoline-5-thiones. Farmaco. 2002;57:559–564. doi: 10.1016/S0014-827X(02)01248-X.
  46. El Shehry MF, Abu-Hashem AA, El-Telbani EM. Synthesis of 3-((2,4-dichlorophenoxy)methyl)-1,2,4-triazolo (thiadiazoles and thiadiazines) as anti-inflammatory and molluscicidal agents. Eur J Med Chem. 2010;45:1906–1911. doi: 10.1016/j.ejmech.2010.01.030.
  47. Gadad AK, Noolvi MN, Karpoormath RV. Synthesis and anti-tubercular activity of a series of 2-sulfonamido /trifluoromethyl-6-substituted imidazo-[2,1-b]-1,3,4-thiadiazole derivatives. Bioorg Med Chem. 2004;12:5651–5659. doi: 10.1016/j.bmc.2004.07.060.
  48. Gülerman NN, Doğan HN, Rollas S, Johansson C, Çelik C. Synthesis and structure elucidation of some new thioether derivatives of 1,2,4-triazoline-3-thiones and their antimicrobial activities. Farmaco. 2001;56:953–958. doi: 10.1016/S0014-827X(01)01167-3.
  49. Nagham Mahmood Aljamali., 2015. Synthesis and Chemical Identification of Macro Compounds of (Thiazol and Imidazol)'.,Research J. Pharm. and Tech, 8,1, 78-84., DOI: 10.5958/0974-360X.2015.00016.5
  50. Zelisko N., Karpenko O., Muzychenko V., Gzella A., Grellier P., Lesyk R. trans-Aconitic acid-based hetero-Diels-Alder reaction in the synthesis of thiopyrano[2,3-d][1,3]thiazole derivatives. Tetrahedron Lett . 2017 ;58:1751–1754. doi: 10.1016/j.tetlet.2017.03.062.
  51. Zelisko N.I., Finiuk N.S., Shvets V.M., Medvid Y.O., Stoika R.S., Lesyk R.B. Screening of spiro-substitutedthiopyrano[2,3-d]thiazoles for their cytotoxic action on tumor cells. Biopolym. Cell. 2017;33:282–290. doi: 10.7124/bc.00095A.
  52. Mestaf M, Nawfel Muhammed Baqer Muhsin., NeuroQuantology, 2019 .,17 (11), 11-16., 10.14704/nq.2019. 17.11.NQ19108.
  53. Miad Mohmed ,Nagham Mahmood Aljamali ,Sabreen Ali Abdalrahman.,Wassan Ala Shubber ., 'Formation of Oxadiazole Derivatives Ligands from Condensation and Imination Reaction with References To Spectral Investigation, Thermal and Microbial Assay'., Biochem. Cell. Arch., 2018 ,18, 1, pp. 847-853
  54. Harish K, Sadique AJ, Suroor AK, Mohammad A. 1,3,4-Oxadiazole/thiadiazole and 1,2,4-triazole derivatives of biphenyl-4-yloxy acetic acid: synthesis and preliminary evaluation of biological properties. Eur J Med Chem. 2008;43:2688–2698. doi: 10.1016/j.ejmech.2008.01.039
  55. Aseel Mahmood Jawad, Nagham Mahmood Aljamali, Aseel M J .,'Innovation, Preparation of Cephalexin Drug Derivatives and Studying of (Toxicity & Resistance of Infection)'., International Journal of Psychosocial Rehabilitation, Vol. 24, Issue 04, 2020 , 3754-3767 ., DOI: 10.37200/IJPR/V24I4/PR201489
  56. Nagham Mahmood Aljamali.,Synthesis of Antifungal Chemical Compounds from Fluconazole with (Pharma-Chemical) Studying, Research journal of Pharmaceutical, biological and chemical sciences, 2017, 8 (3), 564 -573.
  57. Holmwood G, Buechel KH, Plempel M, Haller J (1982) Antimicrobial azoles. ChemAbstr 96:62979s. Patent RFN DE 3018865, 1981
  58. Kaplaushenko AH, Panasenko OI, Knish EH, Scherbina RO. Synthesis, physicochemical and biological properties of 2-(5-R1-4-R2-1,2,4-triazol-3-ylthio)acetic acids. Farm Zh. 2008;2:67–72.
  59. Klimešová V, Zahajská L, Waisser K, Kaustová J, Möllmann U. Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. Farmaco. 2004;59:279–288. doi: 10.1016/j.farmac.2004 .01.006 .
  60. Kumar D, Kumar NM, Chang K-H, Shah K. Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazoles . Eur J Med Chem. 2010;45:4664–4668. doi: 10.1016/j.ejmech.2010.07.023.
  61. Nawfel Muhammed Baqer Muhsin, Hayder H K, Noor H D, Nagham Mahmood Aljamali., 'Preparation of Chemical Inhibitors to Treat the Corrosion and Erosion of Machines', International Journal of Engineering, Applied and Management Sciences Paradigms.,2019, 54,3,89-93.
  62. Liesen AP, De Aquino TM, Carvalho CS, Lima VT, De Araújo JM, De Lima JG, De Faria AR, De Melo EJT, Alves AJ, Alves EW, Alves AQ, Góes AJS. Synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities of thiosemicarbazides, 4-thiazolidinones and 1,3,4-thiadiazoles. Eur J Med Chem. 2010;45:3685–3691. doi: 10.1016/j.ejmech.2010.05.017.
  63. McGinnis MR, Pasarell L, Sutton DA, Fothergill AW, Cooper CR, Rinaldi MG. Antimicrob Agents Chemother. 1997;41:1832–1834.
  64. Oxford Diffraction, Xcalibur CCD System (2006) CrysAlis Software System, Version 1.171. Oxford Diffraction Ltd., Abingdon.
  65. Padmavathi V, Sudhakar Reddy G, Padmaja A, Kondaiah P, Ali-Shazia Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. Eur J Med Chem. 2009;44:2106–2112.
  66. Meaad M ,NaghamMahmoodAljamali ,Nadheema A A .,'Preparation,Spectral Investigation, Thermal Analysis, Biochemical Studying of New (Oxadiazole -Five Membered Ring)-Ligands'.,Journal of Global Pharmacy Technology,2018;10,1,20-29.
  67. Ramasubbu N, Parthasarathy R. Short S…O contacts: structure of 2,5-bis(p-methoxyphenylhydroxymethyl) thiophene. ActaCrystallogr C. 1989;45:457–460. doi: 10.1107/S010827 0188010728.
  68. Sheldrick GM. A short history of SHELX. ActaCrystallogr A. 2008;64:112–122. doi: 10.1107/S0 108767307043930.
  69. Shiradkar MR, Murahari KK, Gangadasu HR, Suresh T, KalyanChA, Panchal D, Kaur R, Burange P, Ghogare J, Mokale V, Raut M. Synthesis of new S-derivatives of clubbed triazolylthiazole as anti-Mycobacterium tuberculosis agents. Bioorg Med Chem. 2007;15:3997–4008. doi: 10.1016/j.bmc. 2007.04.003.
  70. Siwek A, Paneth P. Computational studies of the cyclization of thiosemicarbazides. J Phys Org Chem. 2007;20:463–468. doi: 10.1002/poc.1179.
  71. Siwek A, Wujec M, Dobosz M, Wawrzycka-Gorczyca I. Study of direction of cyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides. Heteroat Chem. 2010;21(7):521–532. doi: 10.1002/hc.20643 .
  72. Ulusoy N, Gürsoy A, Ötük G. Synthesis and antimicrobial activity of some 1,2,4-triazole-3-mercaptoacetic acid derivatives. Farmaco. 2001;56:947–952. doi: 10.1016/S0014-827X(01)01128-4.
  73. Wei Q-L, Zhang S-S, Gao J, Li W-H, Xu L-Z, Yu Z-G. Synthesis and QSAR studies of novel triazole compounds containing thioamide as potential antifungal agents. Bioorg Med Chem. 2006;14:7146–7153. doi: 10.1016/j.bmc.2006.06.065.
  74. White EL, Suling WJ, Ross LJ, Seitz LE, Reynolds RC. 2-Alkoxycarbonylaminopyridines: inhibitors of Mycobacterium tuberculosis FtsZ. J AntimicrobChemother. 2002;50:111–114. doi: 10.1093/ jac/dkf075.
  75. Wilson AJC, editor. International tables for crystallography. Dordrecht: Kluwer Academic Publishers; 1995.
  76. Wujec M, Paneth P. Mechanism of 4-methyl-1,2,4-triazol-3-thiole reaction with formaldehyde. A DFT study. J Phys Org Chem. 2007;20:1043–1049. doi: 10.1002/poc.1250.
  77. Polovkovych S.V., Karkhut A.I., Marintsova N.G., Lesyk R.B., Zimenkovsky B.S., Novikov V.P. Synthesis of New Schiff Bases and Polycyclic Fused Thiopyranothiazoles Containing 4,6-Dichloro-1,3,5-Triazine Moiety. J. Heterocycl. Chem. 2013;50:1419–1424. doi: 10.1002/jhet.890 .
  78. Metwally N.H. A convenient synthesis of some new 5-substituted-4-thioxo-thiazolidines and fused thiopyrano[2,3-d]thiazole derivatives. Phosphorus Sulfur Silicon Relat. Elem. 2008;183:2073–2085. doi: 10.1080/10426500 701849105.
Download PDF
Back