Recent Advances in Sulfadiazine's Preparation, Reactions and Biological Applications
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Received: 10 March 2021 Revised: 26 April 2021 Accepted: 12 May 2021 DOI: 10.22034/ ecc.2021.280357.1159 FULL PAPER Recent advances in sulfadiazine's preparation, reactions and biological applications Mahmood M. Fahad*,a |Mohammed G.A. Alkhuzaiea |Shahad F. Alib aDepartment of Chemical Industries, Institute of Sulfa drugs have great attraction due to their wide applications Technology-Baghdad, Middle Technical in medicine, pharmacology and other sciences. One of the most University, Iraq important compounds of Sulfa drugs family is sulfadiazine bDepartment of Pharmacy, Al-Esraa University compound (SDA). It is considered as one of the most important College, Baghdad, Iraq antibiotics that is used in treatment of many diseases such as urinary tract infections (UTIs), toxoplasmosis, malaria and other cases. Due to vital role of sulfadiazine in our life, this review focused on the sulfadiazine properties, preparation methods, reactions and its biological applications. *Corresponding Author: Mahmood M. Fahad KEYWORDS Tel.: +9647804181764 Sulfadiazine; preparation; reactions; biological activity. Introduction Numerous chemotherapeutically important sulfa compounds as sulfadiazine (silver Sulfadiazine is one of the most important sulfadiazine, Silvadene), Sulfamerazine, antibiotics in medicines, which is known as a Sulfathiazole, etc, have (-SO2NH-) part, as a sulfa drug or the sulfonamide group. toxophoric functional group [12]. Their According to the IUPAC system, this heterocyclic moiety contains sulfur(S), compound is called as 4-amino-N-pyrimidin- oxygen (O) or nitrogen (N) atoms that 2-yl-benzenesulfonamide, as shown in Figure improve their biological activities [13]. 1. Sulfadiazine compound has some physiochemical properties such as being a Synthesis of sulfadiazine white, odorless crystalline powder, modestly The common synthesis of sulfadiazine soluble in acetone (CH3)2CO and alcohol, dissolvable in water, molar mass; 250.28 compound usually starts from acetylation of g·mol−1 and melting point; 252-256 °C. This aniline derivatives 1 by reaction with acetic drug is used in the medical field to treat anhydride to give acetanilide derivative 2. urinary tract infections, as a topical agent to Acetanilide derivatives react with the treatment of a burn and wound infections Chlorosulfonic acid to produce 4- and in the veterinary and human therapy [1- acetylaminobenzenesulfonyl chloride 3. On 11]. the other hand, the 2-aminopyrimidine 4 was prepared by reaction two molecules of tetramethoxypropane with guanidine salt. In the final stage, the 4- acetylaminobenzenesulfonyl chloride was reacted with 2-aminopyrimidine to give an Figure 1 Structure of sulfadiazine Eurasian Chem. Commun. 3 (2021) 383-391 http:/echemcom.com P a g e | 383 P a g e | 384 M.M. Fahad et al. acetanilide derivative 5 which hydrolyzed by compound (6), Scheme 1[14-15]. using NaOH solution to form sulfadiazine SCHEME 1 Synthesis of sulfadiazine compound Reactions of sulfadiazine Salim et al. [17], Synthesized azo derivative by treatment of sulfadiazine 7 with solution There are two reactive groups in sulfadiazine of nitrite in the presence of acidic medium to compounds by which sulfadiazines involve in afford diazonium salt 8, the latter reacts with many chemical reactions; one is the aromatic Gamma-resorsolic acid in the presence of amine and another is sulfonamide group. basic medium to produce compound 9, Scheme 2. Reaction of amine group SCHEME 2 Synthesis of Azo dye from sulfadiazine compound Recent advances in sulfadiazine's preparation … P a g e | 385 In Scheme 3, Ahmed [18], Synthesized of then, the result compound 11 reacted with (4-azido-N-(pyrimidin-2-yl) phenylsulfon- sodium azide. In addition, 1,2,3-Triazoline amid) derivatives by coupling reaction, in the derivatives was prepared by reaction of azido first step, sulfadiazine 10 reacted with 12 derivative with chalcones and unsaturated sodium nitrite in the presence of HCl solution, compounds. SCHEME 3 Synthesis of Azo and 1,2,3-triazoline derivatives The [Chloro-N-(4-(N-pyrimidin-2- (pyrimidin-2-yl)benzene sulfonamide]. This ylsulfamoyl) phenyl) acetamide]compound, derivative reacted with different aromatic thiourea and anhydrous potassium carbonate aldehydes in the presence of glacial acetic (K2CO3) in absolute ethanol were heated acid to form Schiff bases derivatives, Scheme under reflux on water bath for 12 hours to 4 [19]. form [4-(2-aminothiazol-4-ylamino)-N- SCHEME 4 Synthesis of Sulfadiazine derivatives Tetrazole derivative was prepared in good phenyl) acetamid and Schiff bases yields by 1,3- dipolar_cyclo addition reactions derivatives, Scheme 5 [20]. of 2-azido-N(4-(N-pyrimidin-2ylsulfamoyl)- P a g e | 386 M.M. Fahad et al. SCHEME 5 Synthesis of Tetrazole derivatives Sangar A. et al. [21] prepared 2- sulfadiazine with different substituted azetidinone derivatives and pyrrolone aldehydes to form schiff base derivatives; the derivatives as antioxidant agents with latter compounds were reacting with antibacterial activity against two kinds of chloroacetyl chloride and fumaryl chloride in bacteria (Staphylococcus aureus and the presence of triethylamine, respectively, Escherichia coli) via condensation of Scheme 6. SCHEME 6 Synthesis of 2-azetidinone derivatives and pyrrolone derivatives Iman K et al. [22] prepared a series of 1,3- dizaonium slat of sulfadiazine with O-tolidine, oxazepine derivatives and 1,3-dizepene Scheme 7. derivatives. The first step was the reaction of SCHEME 7 Synthesis of O-tolidine derivatives Recent advances in sulfadiazine's preparation … P a g e | 387 M.G. Gündüz et al. [23] prepared two novel /sulfathiazole compounds in the presence of acridine and sulfonamide scaffolds from a catalytic amount of p-toluene sulfonic acid, reaction 5,5-dimethyl-1,3-cyclohexanedione, Scheme 8. 2,3-dichlorobenzaldehyde with sulfadiazine SCHEME 8 Synthesis of acridine-(sulfadiazine/sulfathiazole) Derivatives Wissam [24] showed the reaction of with (maleic anhydride, phthalic anhydride) sulfadiazine as starting material with and sodium azide to give (Oxazepine) and substituted benzaldehydes to yield Schiff Tetrazole derivatives, respectively, Scheme 9. base derivatives. These derivatives reacted SCHEME 9 Synthesis of Oxazepine and Tetrazole derivatives Hawraa [25] synthesized new complexes of Schiff base derived from sulfadiazine (Scheme 10). P a g e | 388 M.M. Fahad et al. SCHEME 10 Synthesis of Oxazepine and Tetrazole derivatives Reaction of sulfonamide group alkylated the nitrogen atom in the sulfonamide group to form diaziridine, In these reactions, the amine group must be diazirine and diazetidin derivatives, Scheme protected and blocked before the sulfomide 11. group interacts with other compounds. Nabeel jebor ALganabi et al [26] prepared a series of sulfadiazine derivatives by SCHEME 11 Synthesis of Sulfadiazine derivatives Recent advances in sulfadiazine's preparation … P a g e | 389 Biological applications of sulfadiazine sulfadiazine prevents infection from spreading. The remaining bacteria either die Sulfadiazine is considered as standard in the end or are repelled by the immune therapy for the conservative treatment of system [28-29]. burn wounds [27]. The drug sulfadiazine A.Khdur et al. [30] prepared some new β- inhibits bacteria from making folic acid, so Lactam derivatives from Azo Sulfadiazine as bacteria cannot manufacture DNA so it is not anticancer compounds, Figure 2. a step to increase the numbers. Thus, FIGURE 2 Synthesis of β-Lactam Derivatives Martin et al. [31] prepared Sulfadiazine- 5-nitrofuran-2-carbaldehyde. These derived Schiff bases by the condensation compounds show antimicrobial activity and between sulfadiazine with Salicylaldehydes & cytotoxicity properties, Figure 3. FIGURE 3 Synthesis of Sulfadiazine-derived Schiff bases Mahmood et al. [32] synthesized phenobarbital and their derivatives in the Barbituric acids derivatives by reaction of 2- presences NaOH and K2CO3 respectively. The chloro-N-(4-(4-(N-pyrimidin-2-yl- yield products show antibacterial and sulfamoyl)phenyl-amino)thiazol-2-yl) antifungal activity, Figure 4. acetamide compound with barbital, FIGURE 4 Synthesis of Barbituric acids derivatives P a g e | 390 M.M. Fahad et al. 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