Lipase‐mediated multicomponent synthesis of 1H‐Pyrazolo[1,2‐b]phthalazine‐5,10‐dione derivatives in a binary solvent medium

A new method for the synthesis of 1H‐pyrazolo[1,2‐b]phthalazine‐5,10‐dione derivatives via lipase from the Aspergillus niger–catalyzed multicomponent reaction of aldehydes, malononitrile, and phthalhydrazide is reported herein for the first time. This novel method holds several advantages, including its efficiency, environmental friendliness, simple workup procedure, and good yield (70–86%). The effects of temperature, organic solvents, and water content were investigated. This protocol has the potential to replace traditional chemical synthesis routes for the synthesis of nitrogen‐containing heterocyclic compounds.

[1]  W. Masamba,et al.  Bio-Catalysis in Multicomponent Reactions , 2020, Molecules.

[2]  B. Chaudhari,et al.  Lipase from Porcine Pancreas: An Efficient Biocatalyst for the Synthesis of ortho -Aminocarbonitriles , 2018, ChemistrySelect.

[3]  B. Chaudhari,et al.  Hen Egg White Lysozyme Catalyzed Efficient Synthesis of 3-Indolyl-3-hydroxy Oxindole in Aqueous Ethanol , 2018, Catalysis Letters.

[4]  B. M. Travália,et al.  Effect of parameters on butyl butyrate synthesis using novel Aspergillus niger lipase as biocatalyst , 2018, Acta Scientiarum. Technology.

[5]  V. Dabholkar,et al.  Synthesis of 1H-pyrazolo[1, 2-b]phthalazine-5,10-dione derivatives using NiFe 2 O 4 Nanoparticle as a Heterogeneous Catalyst , 2018 .

[6]  A. Davoodnia,et al.  Preparation, characterization, and first catalytic application of a novel phosphotungstic acid-containing ionic liquid immobilized on CuFe2O4@SiO2 magnetic nanoparticles in the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones , 2017, Russian Journal of General Chemistry.

[7]  B. Maleki,et al.  A new simple method for the preparation of PbO nanoparticles and implementation of an efficient and reusable catalytic system for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones , 2017, Journal of the Iranian Chemical Society.

[8]  M. Maghsoodlou,et al.  Copper(II) acetate monohydrate: an efficient and eco-friendly catalyst for the one-pot multi-component synthesis of biologically active spiropyrans and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives under solvent-free conditions , 2016, Research on Chemical Intermediates.

[9]  Jung-Min Choi,et al.  Industrial applications of enzyme biocatalysis: Current status and future aspects. , 2015, Biotechnology advances.

[10]  T. Tan,et al.  Lipase-catalyzed Knoevenagel condensation in water–ethanol solvent system. Does the enzyme possess the substrate promiscuity? , 2015 .

[11]  Ling-Yu Li,et al.  Hydrolase-catalyzed asymmetric carbon–carbon bond formation in organic synthesis , 2015 .

[12]  A. Chaskar Deep Eutectic Mixture Catalyzed One-Pot Three-Component Synthesis of 1H-pyrazolo and 2H-indazolo Phthalazines , 2014 .

[13]  R. Chauhan,et al.  A Rapid and an Efficient Route to the One‐pot, Multicomponent Synthesis of 1H‐Pyrazolo[1,2‐b]phthalazine‐5,10‐dione Ring Systems , 2014 .

[14]  P. Koehler,et al.  Lipases in wheat breadmaking: analysis and functional effects of lipid reaction products. , 2014, Journal of agricultural and food chemistry.

[15]  Eelco Ruijter,et al.  Multicomponent reactions: advanced tools for sustainable organic synthesis , 2014 .

[16]  Huizhen Liu,et al.  Henry reaction catalyzed by Lipase A from Aspergillus niger , 2013 .

[17]  G. Bez,et al.  Multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles catalyzed by lipase from Aspergillus niger , 2013 .

[18]  E. Assaf,et al.  Enzymatic Esterification of Oleic Acid with Aliphatic Alcohols for the Biodiesel Production by Candida antarctica Lipase , 2013, Catalysis Letters.

[19]  Zhi Guan,et al.  One-pot four-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives , 2012 .

[20]  A. Pandurangan,et al.  Post synthesis alumination of KIT-6 materials with Ia3d symmetry and their catalytic efficiency towards multicomponent synthesis of 1H-pyrazolo[1,2-]phthalazine-5,10-dione carbonitriles and carboxylates , 2012 .

[21]  M. N. Gupta,et al.  Lipase promiscuity and its biochemical applications , 2012 .

[22]  L. Protesescu,et al.  Efficient bio-conversion of glycerol to glycerol carbonate catalyzed by lipase extracted from Aspergillus niger , 2012 .

[23]  D. Raghuvanshi,et al.  A highly efficient green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives and their photophysical studies , 2011 .

[24]  E. Jurado,et al.  Optimization of Lipase Performance in Detergent Formulations for Hard Surfaces , 2011 .

[25]  D. O'Hagan Fluorine in health care: Organofluorine containing blockbuster drugs , 2010 .

[26]  M. Nabid,et al.  Ultrasound-assisted one-pot, three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. , 2010, Ultrasonics sonochemistry.

[27]  M. G. Nascimento,et al.  Potential application of native lipases in the resolution of (RS) - phenylethylamine , 2010 .

[28]  D. Gokhale,et al.  Purification and characterization of acidic lipase from Aspergillus niger NCIM 1207. , 2009, Bioresource technology.

[29]  A. Bazgir,et al.  An Efficient One-Pot Synthesis of 1 H -Pyrazolo[1,2- b ]phthalazine-5,10-dione Derivatives , 2008 .

[30]  Jin Sung Kim,et al.  Synthesis of 1-/2-substituted-[1,2,3]triazolo[4,5-g]phthalazine-4,9-diones and evaluation of their cytotoxicity and topoisomerase II inhibition. , 2008, Bioorganic & medicinal chemistry.

[31]  C. Ryu,et al.  Synthesis and antifungal activity of 6-arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones. , 2007, Bioorganic & medicinal chemistry letters.

[32]  Yunjun Yan,et al.  [Purification and characterization of a lipase from Aspergillus niger F044]. , 2007, Sheng wu gong cheng xue bao = Chinese journal of biotechnology.

[33]  P. Carvalho,et al.  Esterification of (RS)-Ibuprofen by native and commercial lipases in a two-phase system containing ionic liquids , 2006 .

[34]  P. Gong,et al.  Synthesis and anticancer activities of novel 1,4-disubstituted phthalazines. , 2006, Molecules.

[35]  P. Carvalho,et al.  Optimization of enantioselective resolution of racemic ibuprofen by native lipase from Aspergillus niger , 2006, Journal of Industrial Microbiology and Biotechnology.

[36]  Y. K. Rao,et al.  Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors. , 2004, Bioorganic & medicinal chemistry letters.

[37]  J. Leonard,et al.  Pharmacological evaluation of some new 1-substituted-4-hydroxy-phthalazines. , 2002, European journal of medicinal chemistry.

[38]  F. Lichtenthaler,et al.  Unsaturated O- and N-heterocycles from carbohydrate feedstocks. , 2002, Accounts of chemical research.

[39]  M. Searcey,et al.  A convenient access to benzo-substituted phthalazines as potential precursors to DNA intercalators , 2001 .

[40]  M. Baraldi,et al.  Synthesis and anticonvulsant activity of novel and potent 6,7-methylenedioxyphthalazin-1(2H)-ones. , 2000, Journal of medicinal chemistry.

[41]  S. Swaney,et al.  Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: lead identification and SAR of 3- and 4-substituted derivatives. , 2000, Journal of medicinal chemistry.

[42]  K. Miyazaki,et al.  4-Benzylamino-1-chloro-6-substituted phthalazines: synthesis and inhibitory activity toward phosphodiesterase 5. , 1998, Journal of medicinal chemistry.

[43]  P. Punt,et al.  Efficient production of secreted proteins by Aspergillus : progress, limitations and prospects , 1997, Applied Microbiology and Biotechnology.

[44]  Andrew Simon Bell,et al.  Sildenafil (VIAGRATM), a potent and selective inhibitor of type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction , 1996 .

[45]  K. Kubo,et al.  Studies on cardiotonic agents. II. Synthesis of novel phthalazine and 1,2,3-benzotriazine derivatives. , 1990, Chemical & pharmaceutical bulletin.

[46]  A. Macrae Lipase-catalyzed interesterification of oils and fats , 1983 .

[47]  M. Kira,et al.  Synthesis of new pyrazolones as potent anti-inflammatory agents. , 1978, Journal de pharmacie de Belgique.

[48]  F. Bergstrom Heterocyclic Nitrogen Compounds. Part IIA. Hexacyclic Compounds: Pyridine, Quinoline, and Isoquinoline. , 1944 .