MgO‐Nanoparticle‐Catalyzed Synthesis and Evaluation of Antimicrobial and Antioxidant Activity of New Multi‐Ring Compounds Containing Spiro[indoline‐3,4′‐[1,3]dithiine]

Abstract

Multi‐component reaction indoline‐2,3‐dione derivatives, malononitrile, carbon disulfide and dimedone have led to newly synthesized 6′‐amino‐2′‐(4,4‐dimethyl‐2,6‐dioxocyclohexylidene)‐2‐oxospiro[indoline‐3,4′‐[1,3]dithiine]‐5′‐carbonitrile derivatives under acidic and base conditions with high efficiency during a simplified process. In acidic conditions, using MgO nanoparticleas as a catalyst, greater yields in shorter time was observed. The biological effects of synthetic derivatives such as antibacterial and antifungal effects based on inhibition zone diameter, minimum inhibitory concentration, minimum bactericidal concentration, minimum fungicidal concentration and antioxidant effects on DPPH free radical, have been the subject of previous studies. The results showed that some derivatives show higher antimicrobial effects compared to commercial drugs.

Synthesis of bioactive magnetic nanoparticles spiro[indoline‐3,4′‐[1,3]dithiine]@Ni (NO3)2 supported on Fe3O4@SiO2@CPS as reusable nanocatalyst for the synthesis of functionalized 3,4‐dihydro‐2H‐pyran

“…The absorption peak for Ni‐N, appeared in regions 532 cm −1 . According to a previous report , in the IR spectrum of the 6′‐amino‐2′‐(4,4‐dimethyl‐2,6‐dioxocyclohexylidene)‐2‐oxospiro[indoline‐3,4′‐[1,3]dithiine]‐5′‐carbonitrile, frequency regarding to N‐H in spiro part was appeared at 3144 cm −1 , but in the IR spectrum of the magnetic nanoparticles, stretching vibration of N‐H appeared in region 3433 cm −1 , so the nickel metal was attached to the nitrogen of the spiro part and the broad bond at 3433 cm −1 was related to the N‐H of aliphatic part.…”

“…In the third step, Fe 3 O 4 @SiO 2 @CPS were synthesized from the reaction of Fe 3 O 4 @SiO 2 and CPTMS compounds . In the fourth step, the composition including 6′‐amino‐2′‐(4,4‐dimethyl‐2,6‐dioxocyclohexylidene)‐2‐oxospiro[indoline‐3,4′‐[1,3]dithiine]‐5′‐carbonitrile was synthesized according to our previous method, then from its reaction with the products obtained from previous step in toluene, spiro[indoline‐3,4′‐[1,3]dithiine] supported on Fe 3 O 4 @SiO 2 @CPS, was synthesized. In the final step, from reaction between spiro[indoline‐3,4′‐[1,3]dithiine] supported on Fe 3 O 4 @SiO 2 @CPS with Ni (NO 3 ) 2 , the desired magnetic nanoparticles spiro[indoline‐3,4′‐[1,3]dithiine]@Ni (NO 3 ) 2 supported on CPTMS‐Fe 3 O 4 @SiO 2 was synthesized (Scheme ).…”

“…Using the method presented by Ghazanfari et al, 6′‐amino‐2′‐(4, 4‐dimethyl‐2, 6‐dioxocyclohexylidene)‐2‐oxospiro [indoline‐3,4′‐[1,3]dithiine]‐5′‐carbonitrile was also synthesized …”

Synthesis, Characterization and Antimicrobial Evaluation of Novel 6’-Amino-spiro[indeno[1,2-b] quinoxaline[1,3]dithiine]-5’-carbonitrile Derivatives

“…In our previous report, new derivatives of spiro[indoline-3,4ʹ- [1,3]dithiine] were synthesized by MgO nanoparticles. 17 In this work, the synthesis of derivatives with MgO nanoparticles was investigated but the desired result was not obtained, that could be due to the larger reactant material including 11H-indeno [1,2-b]quinoxalin-11-one than in the previous work.…”

“…14 Other biological properties have also been reported for synthesized heterocyclic compounds containing l,3-dithiin ring. [15][16][17] These compounds are most often used as a carbon protection groups for the synthesis of heterocyclic compounds. [18][19][20] In this study the new derivatives of 6'-amino-2'-(arylidene)spiro[indeno [1,2-b]quinoxaline [1,3]dithiine]-5'-carbonitrile were synthesized using compounds possessing active methylene group, carbon disulfide, malononitrile, 11H-indeno [1,2-b]quinoxalin-11-one and 1H-indene-1,2,3-trione and their biological activities such as antibacterial and antifungal activities were studied.…”