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Synthesis and antioxidant activity of benzo[a]pyrano[2,3- c] phenazine derivative compound via one-pot multicomponent reaction

Yıl 2022, Cilt: 26 Sayı: 4, 954 - 961, 28.06.2025

Agus Rimus Liandi , Antonius Herry Cahyana

Öz

Phenazine derivative compounds are of concern because of their extraordinary activities in medicine. The aim of this study is to synthesize the derivative of benzo[a]pyrano[2,3-c] phenazine compound based on lawsone with caffeine catalyst using the one-pot multicomponent reaction method and test its antioxidant activity. The formation of the target compound was evaluated for functional group vibration, maximum wavelength, and molecular weight by FTIR, UV-Vis Spectrophotometer, and LCMS, which showed the characteristics of the benzo[a]pyrano[2,3-c] phenazine compound. The synthesized compound was 3-amino-2-cyano-1-(2-hydroxyl-phenyl)-1H-benzo[a]pyrano[2,3-c] phenazine with the molecular formula C26H16N4O2. At the optimum condition of the reaction, the use of caffeine catalyst was able to give a product yield of 67.2%. The potential of the synthesized compound as an antioxidant could be classified as a good antioxidant with an IC50 value of 14.26 ppm.

Anahtar Kelimeler

Benzo[a]pyrano[2 3-c] phenazine lawsone one-pot multicomponent reaction antioxidant caffeine catalyst

Kaynakça

  • [1] Cheng B, He Y, Yang H, Li H, Zhang X, Xu W, Sun H, Wang T, Zhai H. Synthesis of pyrazolotetrazepin-7-ones from 1,3,5-triazinanes with N,N′-cyclic azomethine imines via a formal (5+2) pathway. Tetrahedron. 2021; 89: 132130. [CrossRef]
  • [2] Gu B, Wu S, Xu H, Yang W, Liu Z, Deng W. Organocatalytic asymmetric [3+3] annulation of isatin N,N’-cyclic azomethine imines with enals: Efficient approach to functionalized spiro N-heterocyclic oxindoles. Chinese Chem Lett. 2021; 32(2): 672-675. [CrossRef]
  • [3] Le-Nhat-Thuy G, Dang Thi TA, Nguyen Thi QG, Thi PH, Nguyen TA, Nguyen HT, Nguyen Thi TH, Nguyen HS, Nguyen TV. Synthesis and biological evaluation of novel benzo[a]pyridazino[3,4-c]phenazine derivatives. Bioorganic Med Chem Lett. 2021; 43: 128054. [CrossRef]
  • [4] Cha JW, Lee S Il, Kim MC, Thida M, Lee JW, Park JS, Kwon HC. Pontemazines A and B, phenazine derivatives containing a methylamine linkage from Streptomyces sp. UT1123 and their protective effect to HT-22 neuronal cells. Bioorganic Med Chem Lett. 2015; 25(22): 5083-5086. [CrossRef]
  • [5] Shaterian HR, Moradi F, Mohammadnia M. Nano copper(II) oxide catalyzed four-component synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives. Comptes Rendus Chim. 2012; 15(11-12): 1055-1059. [CrossRef]
  • [6] Nagaraju P, Reddy PN, Padmaja P, Ugale VG. Synthesis, antiproliferative activity and molecular docking studies of novel benzo[a]pyrano-[2,3-c]phenazine derivatives. Chem Data Collect. 2020;30:100541. [CrossRef]
  • [7] Muller M, Sorrell TC. Inhibition of the human platelet cyclooxygenase response by the naturally occurring phenazine derivative, 1-hydroxyphenazine. Prostaglandins. 1995;50(5-6):301-311. [CrossRef]
  • [8] Laursen JB, Nielsen J. Phenazine natural products: Biosynthesis, synthetic analogues, and biological activity. Chem Rev. 2004; 104(3): 1663-1685. [CrossRef]
  • [9] Gamage SA, Spicer JA, Rewcastle GW, Milton J, Sohal S, Dangerfield W, Mistry P, Vicker N, Charlton PA, Denny WA. Structure-activity relationships for pyrido-, imidazo-, pyrazolo-, pyrazino-, and pyrrolophenazinecarboxamides as topoisomerase-targeted anticancer agents. J Med Chem. 2002; 45(3): 740-743. [CrossRef]
  • [10] Ligon JM, Hill DS, Hammer PE, Torkewitz NR, Hofmann D, Kempf HJ, Pée KV. Natural products with antifungal activity from Pseudomonas biocontrol bacteria. Pest Manag Sci. 2000; 56(8): 688-695. [CrossRef]
  • [11] Chater KF. Streptomyces inside-out: A new perspective on the bacteria that provide us with antibiotics. Philos Trans R Soc B Biol Sci. 2006; 361(1469): 761-768. [CrossRef]
  • [12] Alameddine B, Baig N, Shetty S, Al-Mousawi S. Conjugated copolymers bearing 2,7-di(thiophen-2-yl)phenanthrene- 9,10-dione units and alteration of their emission via functionalization of the ortho-dicarbonyl groups into quinoxaline and phenazine derivatives. Polymer. 2019; 178: 121589. [CrossRef]
  • [13] Yousif D, Monti M, Papagni A, Vaghi L. Synthesis of phenazines from ortho-bromo azo compounds via sequential Buchwald-Hartwig amination under micellar conditions and acid promoted cyclization. Tetrahedron Lett. 2020; 61(46): 152511. [CrossRef]
  • [14] Hosseiny Davarani SS, Fakhari AR, Shaabani A, Ahmar H, Maleki A, Sheijooni Fumani N. A facile electrochemical method for the synthesis of phenazine derivatives via an ECECC pathway. Tetrahedron Lett. 2008; 49(39): 5622-5624. [CrossRef]
  • [15] Xiong Z, Niu J, Liu H, Xu Z, Li J, Wu Q. Synthesis and bioactivities of Phenazine-1-carboxylic acid derivatives based on the modification of PCA carboxyl group. Bioorganic Med Chem Lett. 2017; 27(9): 2010-2013. [CrossRef]
  • [16] Daraie M, Tamoradi T, Heravi MM, Karmakar B. Ce immobilized 1H-pyrazole-3,5-dicarboxylic acid (PDA) modified CoFe2O4: A potential magnetic nanocomposite catalyst towards the synthesis of diverse benzo[a]pyrano[2,3-c]phenazine derivatives. J Mol Struct. 2021; 1245: 131089. [CrossRef]
  • [17] Teimouri MB, Batebi E, Mohammadnia S, Khavasi HR. Water-controlled selectivity switch in a multicomponent reaction: One-pot stereoselective synthesis of (acyloxymethylidene)chromonyl-furochromones and amido- (acyloxymethylidene)chromones. Tetrahedron. 2021; 96: 132374. [CrossRef]
  • [18] Cahyana AH, Liandi AR, Maghdalena M, Yunarti RT, Wendari TP. Magnetically separable Fe3O4/graphene oxide nanocomposite: An efficient heterogenous catalyst for spirooxindole derivatives synthesis. Ceramics Int. 2022; 1-8. [CrossRef]
  • [19] Javanbakht S, Nazeri MT, Shaabani A, Ghorbani M. Green one-pot synthesis of multicomponent-crosslinked carboxymethyl cellulose as a safe carrier for the gentamicin oral delivery. Int J Biol Macromol. 2020; 164: 2873-2880. [CrossRef]
  • [20] Elbakkay MH, El Rouby WMA, Mariño-López A, Sousa-Castillo A, Salgueiriño V, El-Dek SI, Farghali AA, Correa- Duarte MA, Millet P. One-pot synthesis of TiO2/Sb2S3/RGO complex multicomponent heterostructures for highly enhanced photoelectrochemical water splitting. Int J Hydrogen Energy. 2021; 46(61): 31216-31227. [CrossRef]
  • [21] Galadima A, Masudi A, Muraza O. Catalyst development for tar reduction in biomass gasification: Recent progress and the way forward. J Environ Manage. 2022; 305: 114274. [CrossRef]
  • [22] Shaterian HR, Mohammadnia M. Mild basic ionic liquid catalyzed four component synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives. J Mol Liq. 2013; 177: 162-166. [CrossRef]
  • [23] Yazdani-Elah-Abadi A, Maghsoodlou MT, Mohebat R, Heydari R. Theophylline as a new and green catalyst for the one-pot synthesis of spiro[benzo[a]pyrano[2,3-c]phenazine] and benzo[a]pyrano[2,3 c]phenazine derivatives under solvent-free conditions. Chinese Chem Lett. 2017; 28(2): 446-452. [CrossRef]
  • [24] Ghorbani‑Choghamarani A, Mohammadi M, Shiri L, Taherinia Z. Synthesis and characterization of spinel FeAl2O4 (hercynite) magnetic nanoparticles and their application in multicomponent reactions. Res chem intermed. 2019; 45: 5705-5723 [CrossRef]
  • [25] Daraie M, Tamoradi T, Heravi MM, Karmakar B. Ce immobilized 1 H -pyrazole-3,5-dicarboxylic acid (PDA) modified CoFe2O4 : A potential magnetic nanocomposite catalyst towards the synthesis of diverse benzo[ a ]pyrano[2,3- c ]phenazine derivatives. J Mol Struct. 2021; 1245: 1-8. [CrossRef]
  • [26] Cahyana AH, Mafazi A, Liandi AR. Synthesis of antioxidant agents based on improvement of hydroxyl groups prepared from lawsone compounds. AIP Conf Proceed. 2020; 2242, 1-6. [CrossRef]
  • [27] Oktavia SH, Cahyana AH, Hapsari M, Yunarti RT, Liandi AR. Synthesıs and antımıcrobıal actıvıty of spırooxındolechromene derıvatıve compounds based curcumınoıd and chalcone. Rasayan J Chem. 2021; 14(3), 1990–1997. [CrossRef]
  • [28] Liandi AR, Cahyana AH, Yunarti RT, Wendari TP. Facile synthesis of magnetic Fe3O4@chitosan nanocomposite as environmentally green catalyst in multicomponent Knoevenagel-Michael domino reaction. Ceramics Int. 2022; 1-9. [CrossRef]
  • [29] Nagaraju P, Reddy PN, Padmaja P, Ugale VG. Synthesis, antiproliferative activity and molecular docking studies of novel benzo[a]pyrano-[2,3-c]phenazine derivatives. Chem Data Collec. 2020; 30: 1-8. [CrossRef]
  • [30] Liandi AR, Yunarti RT, Nurmawan MF, Cahyana AH. The Utilization of Fe3O4 nanocatalyst in modifying cinnamaldehyde compound to Synthesis 2-amino-4H-chromene derivative. Mater Today Proc. 2020; 22: 193–198. [CrossRef]
  • [31] Barut B, Şöhretoğlu D. Total phenolic content, cyclooxygenases, α-glucosidase, acetylcholinesterase, tyrosinase inhibitory and DPPH radical scavenging effects of Cornus sanguinea leaves and fruits. J Res Pharm. 2020; 24(5): 623- 631. [CrossRef]
  • [32] Torre MP, Cavero RY, Calvo MI, Vizmanos JL. A Simple and a Reliable Method to Quantify Antioxidant Activity In Vivo. Antioxidants. 2019; 8(5): 1-11. [CrossRef]

Yıl 2022, Cilt: 26 Sayı: 4, 954 - 961, 28.06.2025

Agus Rimus Liandi , Antonius Herry Cahyana

Öz

Kaynakça

  • [1] Cheng B, He Y, Yang H, Li H, Zhang X, Xu W, Sun H, Wang T, Zhai H. Synthesis of pyrazolotetrazepin-7-ones from 1,3,5-triazinanes with N,N′-cyclic azomethine imines via a formal (5+2) pathway. Tetrahedron. 2021; 89: 132130. [CrossRef]
  • [2] Gu B, Wu S, Xu H, Yang W, Liu Z, Deng W. Organocatalytic asymmetric [3+3] annulation of isatin N,N’-cyclic azomethine imines with enals: Efficient approach to functionalized spiro N-heterocyclic oxindoles. Chinese Chem Lett. 2021; 32(2): 672-675. [CrossRef]
  • [3] Le-Nhat-Thuy G, Dang Thi TA, Nguyen Thi QG, Thi PH, Nguyen TA, Nguyen HT, Nguyen Thi TH, Nguyen HS, Nguyen TV. Synthesis and biological evaluation of novel benzo[a]pyridazino[3,4-c]phenazine derivatives. Bioorganic Med Chem Lett. 2021; 43: 128054. [CrossRef]
  • [4] Cha JW, Lee S Il, Kim MC, Thida M, Lee JW, Park JS, Kwon HC. Pontemazines A and B, phenazine derivatives containing a methylamine linkage from Streptomyces sp. UT1123 and their protective effect to HT-22 neuronal cells. Bioorganic Med Chem Lett. 2015; 25(22): 5083-5086. [CrossRef]
  • [5] Shaterian HR, Moradi F, Mohammadnia M. Nano copper(II) oxide catalyzed four-component synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives. Comptes Rendus Chim. 2012; 15(11-12): 1055-1059. [CrossRef]
  • [6] Nagaraju P, Reddy PN, Padmaja P, Ugale VG. Synthesis, antiproliferative activity and molecular docking studies of novel benzo[a]pyrano-[2,3-c]phenazine derivatives. Chem Data Collect. 2020;30:100541. [CrossRef]
  • [7] Muller M, Sorrell TC. Inhibition of the human platelet cyclooxygenase response by the naturally occurring phenazine derivative, 1-hydroxyphenazine. Prostaglandins. 1995;50(5-6):301-311. [CrossRef]
  • [8] Laursen JB, Nielsen J. Phenazine natural products: Biosynthesis, synthetic analogues, and biological activity. Chem Rev. 2004; 104(3): 1663-1685. [CrossRef]
  • [9] Gamage SA, Spicer JA, Rewcastle GW, Milton J, Sohal S, Dangerfield W, Mistry P, Vicker N, Charlton PA, Denny WA. Structure-activity relationships for pyrido-, imidazo-, pyrazolo-, pyrazino-, and pyrrolophenazinecarboxamides as topoisomerase-targeted anticancer agents. J Med Chem. 2002; 45(3): 740-743. [CrossRef]
  • [10] Ligon JM, Hill DS, Hammer PE, Torkewitz NR, Hofmann D, Kempf HJ, Pée KV. Natural products with antifungal activity from Pseudomonas biocontrol bacteria. Pest Manag Sci. 2000; 56(8): 688-695. [CrossRef]
  • [11] Chater KF. Streptomyces inside-out: A new perspective on the bacteria that provide us with antibiotics. Philos Trans R Soc B Biol Sci. 2006; 361(1469): 761-768. [CrossRef]
  • [12] Alameddine B, Baig N, Shetty S, Al-Mousawi S. Conjugated copolymers bearing 2,7-di(thiophen-2-yl)phenanthrene- 9,10-dione units and alteration of their emission via functionalization of the ortho-dicarbonyl groups into quinoxaline and phenazine derivatives. Polymer. 2019; 178: 121589. [CrossRef]
  • [13] Yousif D, Monti M, Papagni A, Vaghi L. Synthesis of phenazines from ortho-bromo azo compounds via sequential Buchwald-Hartwig amination under micellar conditions and acid promoted cyclization. Tetrahedron Lett. 2020; 61(46): 152511. [CrossRef]
  • [14] Hosseiny Davarani SS, Fakhari AR, Shaabani A, Ahmar H, Maleki A, Sheijooni Fumani N. A facile electrochemical method for the synthesis of phenazine derivatives via an ECECC pathway. Tetrahedron Lett. 2008; 49(39): 5622-5624. [CrossRef]
  • [15] Xiong Z, Niu J, Liu H, Xu Z, Li J, Wu Q. Synthesis and bioactivities of Phenazine-1-carboxylic acid derivatives based on the modification of PCA carboxyl group. Bioorganic Med Chem Lett. 2017; 27(9): 2010-2013. [CrossRef]
  • [16] Daraie M, Tamoradi T, Heravi MM, Karmakar B. Ce immobilized 1H-pyrazole-3,5-dicarboxylic acid (PDA) modified CoFe2O4: A potential magnetic nanocomposite catalyst towards the synthesis of diverse benzo[a]pyrano[2,3-c]phenazine derivatives. J Mol Struct. 2021; 1245: 131089. [CrossRef]
  • [17] Teimouri MB, Batebi E, Mohammadnia S, Khavasi HR. Water-controlled selectivity switch in a multicomponent reaction: One-pot stereoselective synthesis of (acyloxymethylidene)chromonyl-furochromones and amido- (acyloxymethylidene)chromones. Tetrahedron. 2021; 96: 132374. [CrossRef]
  • [18] Cahyana AH, Liandi AR, Maghdalena M, Yunarti RT, Wendari TP. Magnetically separable Fe3O4/graphene oxide nanocomposite: An efficient heterogenous catalyst for spirooxindole derivatives synthesis. Ceramics Int. 2022; 1-8. [CrossRef]
  • [19] Javanbakht S, Nazeri MT, Shaabani A, Ghorbani M. Green one-pot synthesis of multicomponent-crosslinked carboxymethyl cellulose as a safe carrier for the gentamicin oral delivery. Int J Biol Macromol. 2020; 164: 2873-2880. [CrossRef]
  • [20] Elbakkay MH, El Rouby WMA, Mariño-López A, Sousa-Castillo A, Salgueiriño V, El-Dek SI, Farghali AA, Correa- Duarte MA, Millet P. One-pot synthesis of TiO2/Sb2S3/RGO complex multicomponent heterostructures for highly enhanced photoelectrochemical water splitting. Int J Hydrogen Energy. 2021; 46(61): 31216-31227. [CrossRef]
  • [21] Galadima A, Masudi A, Muraza O. Catalyst development for tar reduction in biomass gasification: Recent progress and the way forward. J Environ Manage. 2022; 305: 114274. [CrossRef]
  • [22] Shaterian HR, Mohammadnia M. Mild basic ionic liquid catalyzed four component synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives. J Mol Liq. 2013; 177: 162-166. [CrossRef]
  • [23] Yazdani-Elah-Abadi A, Maghsoodlou MT, Mohebat R, Heydari R. Theophylline as a new and green catalyst for the one-pot synthesis of spiro[benzo[a]pyrano[2,3-c]phenazine] and benzo[a]pyrano[2,3 c]phenazine derivatives under solvent-free conditions. Chinese Chem Lett. 2017; 28(2): 446-452. [CrossRef]
  • [24] Ghorbani‑Choghamarani A, Mohammadi M, Shiri L, Taherinia Z. Synthesis and characterization of spinel FeAl2O4 (hercynite) magnetic nanoparticles and their application in multicomponent reactions. Res chem intermed. 2019; 45: 5705-5723 [CrossRef]
  • [25] Daraie M, Tamoradi T, Heravi MM, Karmakar B. Ce immobilized 1 H -pyrazole-3,5-dicarboxylic acid (PDA) modified CoFe2O4 : A potential magnetic nanocomposite catalyst towards the synthesis of diverse benzo[ a ]pyrano[2,3- c ]phenazine derivatives. J Mol Struct. 2021; 1245: 1-8. [CrossRef]
  • [26] Cahyana AH, Mafazi A, Liandi AR. Synthesis of antioxidant agents based on improvement of hydroxyl groups prepared from lawsone compounds. AIP Conf Proceed. 2020; 2242, 1-6. [CrossRef]
  • [27] Oktavia SH, Cahyana AH, Hapsari M, Yunarti RT, Liandi AR. Synthesıs and antımıcrobıal actıvıty of spırooxındolechromene derıvatıve compounds based curcumınoıd and chalcone. Rasayan J Chem. 2021; 14(3), 1990–1997. [CrossRef]
  • [28] Liandi AR, Cahyana AH, Yunarti RT, Wendari TP. Facile synthesis of magnetic Fe3O4@chitosan nanocomposite as environmentally green catalyst in multicomponent Knoevenagel-Michael domino reaction. Ceramics Int. 2022; 1-9. [CrossRef]
  • [29] Nagaraju P, Reddy PN, Padmaja P, Ugale VG. Synthesis, antiproliferative activity and molecular docking studies of novel benzo[a]pyrano-[2,3-c]phenazine derivatives. Chem Data Collec. 2020; 30: 1-8. [CrossRef]
  • [30] Liandi AR, Yunarti RT, Nurmawan MF, Cahyana AH. The Utilization of Fe3O4 nanocatalyst in modifying cinnamaldehyde compound to Synthesis 2-amino-4H-chromene derivative. Mater Today Proc. 2020; 22: 193–198. [CrossRef]
  • [31] Barut B, Şöhretoğlu D. Total phenolic content, cyclooxygenases, α-glucosidase, acetylcholinesterase, tyrosinase inhibitory and DPPH radical scavenging effects of Cornus sanguinea leaves and fruits. J Res Pharm. 2020; 24(5): 623- 631. [CrossRef]
  • [32] Torre MP, Cavero RY, Calvo MI, Vizmanos JL. A Simple and a Reliable Method to Quantify Antioxidant Activity In Vivo. Antioxidants. 2019; 8(5): 1-11. [CrossRef]
Toplam 32 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Farmasotik Kimya
Bölüm Articles
Yazarlar

Agus Rimus Liandi 0000-0003-2045-0247

Antonius Herry Cahyana 0000-0002-2613-765X

Yayımlanma Tarihi 28 Haziran 2025
Yayımlandığı Sayı Yıl 2022 Cilt: 26 Sayı: 4

Kaynak Göster

APA Liandi, A. R., & Cahyana, A. H. (2025). Synthesis and antioxidant activity of benzo[a]pyrano[2,3- c] phenazine derivative compound via one-pot multicomponent reaction. Journal of Research in Pharmacy, 26(4), 954-961.
AMA Liandi AR, Cahyana AH. Synthesis and antioxidant activity of benzo[a]pyrano[2,3- c] phenazine derivative compound via one-pot multicomponent reaction. J. Res. Pharm. Haziran 2025;26(4):954-961.
Chicago Liandi, Agus Rimus, ve Antonius Herry Cahyana. “Synthesis and Antioxidant Activity of benzo[a]pyrano[2,3- C] Phenazine Derivative Compound via One-Pot Multicomponent Reaction”. Journal of Research in Pharmacy 26, sy. 4 (Haziran 2025): 954-61.
EndNote Liandi AR, Cahyana AH (01 Haziran 2025) Synthesis and antioxidant activity of benzo[a]pyrano[2,3- c] phenazine derivative compound via one-pot multicomponent reaction. Journal of Research in Pharmacy 26 4 954–961.
IEEE A. R. Liandi ve A. H. Cahyana, “Synthesis and antioxidant activity of benzo[a]pyrano[2,3- c] phenazine derivative compound via one-pot multicomponent reaction”, J. Res. Pharm., c. 26, sy. 4, ss. 954–961, 2025.
ISNAD Liandi, Agus Rimus - Cahyana, Antonius Herry. “Synthesis and Antioxidant Activity of benzo[a]pyrano[2,3- C] Phenazine Derivative Compound via One-Pot Multicomponent Reaction”. Journal of Research in Pharmacy 26/4 (Haziran 2025), 954-961.
JAMA Liandi AR, Cahyana AH. Synthesis and antioxidant activity of benzo[a]pyrano[2,3- c] phenazine derivative compound via one-pot multicomponent reaction. J. Res. Pharm. 2025;26:954–961.
MLA Liandi, Agus Rimus ve Antonius Herry Cahyana. “Synthesis and Antioxidant Activity of benzo[a]pyrano[2,3- C] Phenazine Derivative Compound via One-Pot Multicomponent Reaction”. Journal of Research in Pharmacy, c. 26, sy. 4, 2025, ss. 954-61.
Vancouver Liandi AR, Cahyana AH. Synthesis and antioxidant activity of benzo[a]pyrano[2,3- c] phenazine derivative compound via one-pot multicomponent reaction. J. Res. Pharm. 2025;26(4):954-61.