Synthesis and microbiological properties of 3-amino-1-hydroxy-2-indolinone and related compounds

Davis, Alvie L.; Smith, David R.; McCord, Tommy J.

doi:10.1021/jm00267a020

Cited by 24 publications

(11 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Nitrophenylglycine was prepared according to published procedures (Davis et al, 1973;Muralidharan and Nerbonne, 1995;England et al, 1997). The amino group was protected with an I 2(aq) labile 4-PO group (Madsen et al, 1995;England et al, 1997), the carboxylic acid was activated as the cyanomethyl ester, and the activated compound was coupled to the dinucleotide dCA, which was then enzymatically ligated to 74-mer THG73 tRNA CUA as detailed previously (Nowak et al, 1995(Nowak et al, , 1998.…”

Section: Methodsmentioning

confidence: 99%

Photochemical Proteolysis of an Unstructured Linker of the GABA_AR Extracellular Domain Prevents GABA but Not Pentobarbital Activation

Hanek

Lester²,

Dougherty³

2010

Mol Pharmacol

View full text Add to dashboard Cite

The GABA type A receptor (GABA A R) is the major inhibitory receptor in the mammalian central nervous system and the target of numerous pharmaceuticals. The ␣-subunit of these pentameric Cys-loop neurotransmitter-gated ion channels contributes to the binding of both GABA and allosteric modulators such as the benzodiazepines, suggesting a role for this subunit in the conformational changes associated with activation of the receptor. Herein we use the nonsense suppression methodology to incorporate a photoactivatable unnatural amino acid and photochemically cleave the backbone of the ␣ subunit of the ␣ 1 ␤ 2 GABA A R in a linker region that is believed to span the subunit. Proteolytic cleavage impairs GABA but not pentobarbital activation, strongly suggesting that conformational changes involving this linker region are critical to the GABA activation pathway.

show abstract

Section: Methodsmentioning

confidence: 99%

Photochemical Proteolysis of an Unstructured Linker of the GABA_AR Extracellular Domain Prevents GABA but Not Pentobarbital Activation

Hanek

Lester²,

Dougherty³

2010

Mol Pharmacol

View full text Add to dashboard Cite

show abstract

“…Indolin-2-one is a most advantageous scaffold which represents an important class of heterocyclic compounds endowed with interesting pharmacological activities such as antimicrobial [3], antioxidant [4], antiviral [5], anti-cholinesterase [6], antibacterial [7], histone deacetylase [8], and anticancer activities [9,10]. Besides, SU4984, SU6668 and BIBF1120 (Figure 1) are the binding with bio-macromolecules like Deoxyribonucleic acid (DNA) has received immense attention since this association can regulate many biochemical functions that take place in cellular system [19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-Proliferative Activity of Biphenyl Derived 5-Substituted-Indolin-2-Ones

Meti¹,

Kamble²,

Kamble³

et al. 2017

Arch Chem Res

View full text Add to dashboard Cite

A series of novel biphenyl derived 5-substituted-indolin-2-one derivatives were synthesized by the reaction of 6-chloro-5-(2-chloroethyl)-indolin-2-one 1 with cyclic secondary amines 2a-h followed by condensation of bromomethylcyanobiphenyl to afford the compounds 5a-h. The nitrile group of 5a-h was converted into tetrazole to obtain the compounds 7a-h and tetrazole of 7a-h was further ring transformed into oxadiazole to get compounds 8a-h. Molecular docking study of these previously unknown molecules was performed on PDB: 453D to analyze the interaction and preferred binding mode of synthesized molecules with DNA. Anti-proliferative activity of these newly synthesized compounds were evaluated against a panel of 60 human cancer cell lines at National Cancer Institute (NCI), Bethesda USA. Among these, seven (07) compounds were evaluated for their anticancer activity. Some of the compounds displayed potent anti-proliferative activity at 10 µM.

show abstract

“…Thiosemicarbazone derivatives of indoline-2,3-dione show appreciable antifungal, antibacterial and antiviral activities in vivo and in vitro (16). New 1,3-dihydro-3-hydroxy-2H-indol-2-ones exhibit promising antibacterial and antifungal activities (17,18). Benzylideneindolone derivatives have potent antimicrobial activity against Staphylococcus aureus at μmol L -1 concentrations (19).…”

mentioning

confidence: 99%

Design, synthesis and molecular modeling study of substituted indoline-2-ones and spiro[indole-heterocycles] with potential activity against Gram-positive bacteria

et al. 2021

View full text Add to dashboard Cite

Longstanding and firsthand infectious diseases are challenging community health threats. A new series of isatin derivatives bearing β-hydroxy ketone, chalcone, or spiro-heterocycle moiety, was synthesized in a good yield. Chemical structures of the synthesized compounds were elucidated using spectroscopic techniques and elemental analysis. Antibacterial activities of the compounds were then evaluated in vitro and by in silico modeling. The compounds were more active against Gram-positive bacteria, Staphylococcus aureus (MIC = 0.026–0.226 mmol L−1) and Bacillus subtilis (MIC = 0.348–1.723 mmol L–1) than against Gram-negative bacteria (MIC = 0.817–7.393 mmol L–1). Only 3-hydroxy-3-(2-(2,5-dimethylthiophen-3-yl)-2-oxoethyl)indolin-2-one (1b) was found as active as imipenem against S. aureus (MIC = 0.026 mmol L–1). In silico docking of the compounds in the binding sites of a homology modeled structure of S. aureus histidine kinase-Walk allowed us to shed light on the binding mode of these novel inhibitors. The highest antibacterial activity of 1b is consistent with its highest docking score values against S. aureus histidine kinase.

show abstract

Synthesis and microbiological properties of 3-amino-1-hydroxy-2-indolinone and related compounds

Cited by 24 publications

References 1 publication

Photochemical Proteolysis of an Unstructured Linker of the GABA_AR Extracellular Domain Prevents GABA but Not Pentobarbital Activation

Photochemical Proteolysis of an Unstructured Linker of the GABA_AR Extracellular Domain Prevents GABA but Not Pentobarbital Activation

Synthesis and Anti-Proliferative Activity of Biphenyl Derived 5-Substituted-Indolin-2-Ones

Design, synthesis and molecular modeling study of substituted indoline-2-ones and spiro[indole-heterocycles] with potential activity against Gram-positive bacteria

Contact Info

Product

Resources

About

Synthesis and microbiological properties of 3-amino-1-hydroxy-2-indolinone and related compounds

Cited by 24 publications

References 1 publication

Photochemical Proteolysis of an Unstructured Linker of the GABAAR Extracellular Domain Prevents GABA but Not Pentobarbital Activation

Photochemical Proteolysis of an Unstructured Linker of the GABAAR Extracellular Domain Prevents GABA but Not Pentobarbital Activation

Synthesis and Anti-Proliferative Activity of Biphenyl Derived 5-Substituted-Indolin-2-Ones

Design, synthesis and molecular modeling study of substituted indoline-2-ones and spiro[indole-heterocycles] with potential activity against Gram-positive bacteria

Contact Info

Product

Resources

About

Photochemical Proteolysis of an Unstructured Linker of the GABA_AR Extracellular Domain Prevents GABA but Not Pentobarbital Activation

Photochemical Proteolysis of an Unstructured Linker of the GABA_AR Extracellular Domain Prevents GABA but Not Pentobarbital Activation