Copper-Catalyzed Asymmetric Synthesis and Comparative Aldose Reductase Inhibition Activity of (+)/(−)-1,2-Benzothiazine-1,1-dioxide Acetic Acid Derivatives

Parveen, Shahida; Hussain, S. Fazal; Qin, Xiangyu; Hao, Xin; Zhu, Shaojuan; Miao, Rui; Zhang, Shuzhen; Fu, Fengyan; Ma, Bing; Yu, Qun; Zhu, Changjin

doi:10.1021/jo500338c

Cited by 11 publications

(10 citation statements)

References 35 publications

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“…There are few examples of high-valent metal complexes that have been used as catalystc ompared to the low-valent transition metal complexes. [16] Therefore, we investigated using our newly developed chiral oxorhenium complexes for imine reduction. We chose to use diphenylphosphinyl-protected imines, because such protecting groupsa re easy to remove, compared to aryl or alkyl groups, and, moreover,t heir bulkiness increases the E/Z ratio in imines, providing conformational restriction, ap rerequisite for efficient asymmetric induction.…”

mentioning

confidence: 99%

Synthesis of Air‐ and Moisture‐Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction

Das

Nallagonda

Dey

et al. 2015

Chemistry A European J

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Air-/moisture-stable, crystalline, and storable chiral salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α-amino esters, γ- and δ-lactams, and isoindolinones have also been carried out using this methodology. Finally, the method has been applied to synthetic targets of pharmaceutical relevance, such as R-(+)-salsolidine and R-(+)-crispine A.

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mentioning

confidence: 99%

Synthesis of Air‐ and Moisture‐Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction

Das

Nallagonda

Dey

et al. 2015

Chemistry A European J

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“…As revealed by the literature, sudoxicam 1 (Figure 1) is an important oxicam having an extended plasma half-life [23], piroxicam 2 (Figure 1), another potent oxicam, is used to cure rheumatoid arthritis, osteoarthritis, and other inflammations [24]. Similarly, various 1,2-benzothiazine 1,1-dioxides have been reported as antileukemic [25][26][27], 11β-HSD1 inhibitors [28], endotheline receptor antagonists [29], antimalarial agents [30], MAO inhibitors [31], antiallergic agents [32], antithrombotics [33], antiparasitic [34], antimicrobials [35,36], antioxidants [37], inhibitors of calpain I [38], and aldose reductase enzymes [39,40]. Our research group is involved in the search for novel and more effective antidiabetic agents [41][42][43][44][45], and in this context we have synthesized novel 1,2-benzothiazine-N-arylacetamides and screened them for their in silico and in vitro α-glucosidase inhibitory potential.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and α-Glucosidase Inhibition Activity of 2-[3-(Benzoyl/4-bromobenzoyl)-4-hydroxy-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl]-N-arylacetamides: An In Silico and Biochemical Approach

et al. 2021

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Diabetes mellitus (DM) is a chronic disorder and has affected a large number of people worldwide. Insufficient insulin production causes an increase in blood glucose level that results in DM. To lower the blood glucose level, various drugs are employed that block the activity of the α-glucosidase enzyme, which is considered responsible for the breakdown of polysaccharides into monosaccharides leading to an increase in the intestinal blood glucose level. We have synthesized novel 2-(3-(benzoyl/4-bromobenzoyl)-4-hydroxy-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl)-N-arylacetamides and have screened them for their in silico and in vitro α-glucosidase inhibition activity. The derivatives 11c, 12a, 12d, 12e, and 12g emerged as potent inhibitors of the α-glucosidase enzyme. These compounds exhibited good docking scores and excellent binding interactions with the selected residues (Asp203, Asp542, Asp327, His600, Arg526) during in silico screening. Similarly, these compounds also showed good in vitro α-glucosidase inhibitions with IC50 values of 30.65, 18.25, 20.76, 35.14, and 24.24 μM, respectively, which were better than the standard drug, acarbose (IC50 = 58.8 μM). Furthermore, a good agreement was observed between in silico and in vitro modes of study.

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“…[4] ALR1is present in all tissues and shows substrate specificity towards toxic aldehydes, such as hydroxynonenal, 3-deoxyglucosone, and methylglyoxal, produced in different pathological conditions associated with oxidative stress as in hyperglycemia [5]. In past years, a range of different molecules has been employed as ALR2 inhibitors [6][7][8][9][10]. Mostly known compounds are carboxylic acids such as tolrestat [11] or cyclic amides like sorbini [12], minalrestat [13] etc.…”

Section: Introductionmentioning

confidence: 99%

Benzopyrazines: Synthesis, Characterization and Evaluation as Aldose Reductase Inhibitors

Bhatti¹,

Zaheer²,

Tehseen³

et al. 2019

SJC

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Role of aldose reductase (ALR2) in diabetic complications such as retinopathy, nephropathy, neuropathy, and cataract etc. is well-evident. ALR2 in the first step of polyol pathway reduces glucose to sorbitol whose elevated level leads to diabetic cataract, characterize by clouding of the lens in the eye that affects vision. Inhibition of ALR2 enzyme with small molecules as inhibitor is a rapid approach for diabetic management. In the present study the synthetic route to synthesize desired benzopyrazines and a library of sixteen (16) methyl benzopyrazines were screened against aldose reductase. From the bioactivity results, the 3'-hydroxyphenyl benzopyrazine 6l was found most active (IC 50 = 1.34 ± 0.07 µM) while 3'bromophenyl analogue 6i showed comparable activity for ALR2 (IC 50 = 3.48 ± 0.66 µM) as compared to standard sorbinil (IC 50 = 3.14 ± 0.02 µM). Both compounds (6l and 6i) showed excellent selectivity for ALR2 over aldehyde reductase (ALR1) which has important role in detoxification of toxic aldehydes. The structure of two regio-isomers were fully characterize by 1 H and 13 C NMR two dimensional NMR techniques including COSY, NOESY, HSQC, and HMBC. Regio-isomers separation was proved to be difficult in different solvent systems. Only an isomer of 3'-bromo benzopyrazine 6i' was isolated that help to assign the structure of regioisomers from NMR data. All the benzopyrazines were fully characterized by using different spectral techniques including 1 H, 13 C NMR, IR spectroscopy, and mass spectrometry.

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Copper-Catalyzed Asymmetric Synthesis and Comparative Aldose Reductase Inhibition Activity of (+)/(−)-1,2-Benzothiazine-1,1-dioxide Acetic Acid Derivatives

Cited by 11 publications

References 35 publications

Synthesis of Air‐ and Moisture‐Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction

Synthesis of Air‐ and Moisture‐Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction

Synthesis and α-Glucosidase Inhibition Activity of 2-[3-(Benzoyl/4-bromobenzoyl)-4-hydroxy-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl]-N-arylacetamides: An In Silico and Biochemical Approach

Benzopyrazines: Synthesis, Characterization and Evaluation as Aldose Reductase Inhibitors

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