1,2-Benzothiazine 1,1-dioxide carboxylate derivatives as novel potent inhibitors of aldose reductase

Chen, Xin; Zhang, Shuzhen; Yang, Yanchun; Hussain, S. Fazal; He, Minlan; Gui, Dequan; Ma, Bing; Jing, Chaojun; Qiao, Zhixin; Zhu, Changjin; Yu, Qun

doi:10.1016/j.bmc.2011.07.051

Cited by 47 publications

(31 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the last years, many ARL2 inhibitors (ARI) have been developed [5, 6] and some of them reached clinical trials to prove their efficacy in preventing and/or modulating/ameliorating DM complications. The most important ARIs can be classified into two chemical groups: (a) cyclic imides , such as sorbinil, fidarestat, minalrestat and ranirestat (AS-3201) [7] and (b) acetic acid derivatives , such as tolrestat, epalrestat, zopolrestat and ponalrestat [8]. To date, only the carboxylic acid epalrestat is available on the market and used for the treatment of diabetic neuropathy in Japan, India and China [9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Functional Evaluation of Novel Aldose Reductase Inhibitors Bearing a Spirobenzopyran Scaffold

Digiacomo¹,

Sartini²,

Nesi³

et al. 2017

TOMCJ

View full text Add to dashboard Cite

Background:Aldose reductase, the first enzyme of the polyol pathway, is the key determinant for the pathogenesis of long term diabetic complications. Accordingly, its inhibition represents the major therapeutic strategy to treat this kind of pathologies. Objectives:In this work we describe the synthesis and the functional evaluation of a number of spiro-oxazolidinone and spiro-morpholinone acetic acid derivatives, and their benzyloxy analogs, developed as aldose reductase inhibitors. Results:Most of them proved to inhibit the target enzyme, showing IC50 values in the micromolar/low micromolar range. SARs observed among the three different series allowed to highlight their key pharmacophoric elements, thus creating sound basis for the design of novel and more effective inhibitors. Conclusion: Although further substitution patterns are needed, the novel compounds here proposed represent a good starting point for the development of novel and effective ARIs.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and Functional Evaluation of Novel Aldose Reductase Inhibitors Bearing a Spirobenzopyran Scaffold

Digiacomo¹,

Sartini²,

Nesi³

et al. 2017

TOMCJ

View full text Add to dashboard Cite

show abstract

“…The racemic 2-[2-(2,4,5-trifluorobenzyl)-1,1-dioxido-3,4-dihydro-2H-1,2-benzothiazin-4-yl]acetic acid ((±)-1) was prepared according to the synthetic pathway reported previously 8 .…”

Section: Synthesis Of Racemic Acid (±)-1mentioning

confidence: 99%

“…The racemic compound (±)-1 was prepared according to the previously reported procedure depicted in Scheme 1 8 , starting with the preparation of the corresponding a,b-unsaturated ester as precursor of the targeted C4-enantiomers. Wittig olefination of the N-substituted ketone 2 with methyl 2-(triphenylphosphoranylidene) acetate provided a,b-unsaturated ester 3…”

Section: Synthetic Chemistrymentioning

confidence: 99%

“…The IC 50 values were determined by linear regression analysis of the log of the concentration-response curve 8 . The results of these biological evaluations are listed in Table 1, and the effectiveness of the test compounds was evaluated with respect to the potent ALR2 inhibitor epalrestat used as a positive control.…”

Section: Aldose Reductase Inhibition and Sar Studiesmentioning

confidence: 99%

“…In our effort to design and synthesize new ARIs, we have found a series of (1,1-dioxide-1,2-benzothiazin-4-yl) substituted acetic acid derivatives ( Figure 1) having good ALR2 inhibitory activity 8 . Particularly, this class has a chiral carbon atom C4 to which the acetate head, the key anion group for binding to ALR2, is attached.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Chiral resolution, determination of absolute configuration, and biological evaluation of (1,2-benzothiazin-4-yl)acetic acid enantiomers as aldose reductase inhibitors

Hao

Qin

Hussain

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

Selective Access to Sultams and Spirocyclic Sultams by the Divergent Annulations of (N‐Aryl)‐Alkynyl Sulphonamides

Raji Reddy,

Rathaur,

Karuna Sagar

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

Herein, we present the first annulation reaction of (N‐aryl)‐alkynyl sulphonamides leading to sultams or spirocyclic sultams. The selective formation of aforesaid products is based on the variable reactivity, intramolecular ortho‐cyclization or dearomative ipso‐annulation, guided by the substituent on N‐aryl group of the substrate. The ortho‐annulation is mediated by electrophile, while the ipso‐annulation is promoted by the radical, enabling the functionalization (selenyl or iodo) on sultams. The synthetic potential of this method is illustrated by modifications of the functional groups present in the products obtained

show abstract

1,2-Benzothiazine 1,1-dioxide carboxylate derivatives as novel potent inhibitors of aldose reductase

Cited by 47 publications

References 32 publications

Synthesis and Functional Evaluation of Novel Aldose Reductase Inhibitors Bearing a Spirobenzopyran Scaffold

Synthesis and Functional Evaluation of Novel Aldose Reductase Inhibitors Bearing a Spirobenzopyran Scaffold

Chiral resolution, determination of absolute configuration, and biological evaluation of (1,2-benzothiazin-4-yl)acetic acid enantiomers as aldose reductase inhibitors

Selective Access to Sultams and Spirocyclic Sultams by the Divergent Annulations of (N‐Aryl)‐Alkynyl Sulphonamides

Contact Info

Product

Resources

About