Spiro heterocycles as potential inhibitors of SIRT1: Pd/C-mediated synthesis of novel N-indolylmethyl spiroindoline-3,2′-quinazolines

Rambabu, D.; Raja, Guttikonda; Sreenivas, B. Yogi; Seerapu, Guru Pavan Kumar; Kumar, K. Lalith; Deora, Girdhar Singh; Haldar, Devyani; Rao, Mandava V. Basaveswara; Pal, Manojit

doi:10.1016/j.bmcl.2012.12.089

Cited by 42 publications

(11 citation statements)

References 29 publications

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“…Melting points were recorded by open capillary method and are uncorrected. NMR spectra were recorded on Bruker AC-300/400 (300/400 MHz for 1 H NMR and 75/100 MHz for 13 absorption spectra were recorded on Specord 210 plus UV Visible-spectrometer and the emission spectrum was recorded on a spectrofluorometer-Jasco, Model-F.P-8300 in DMSO solvent with concentration of 0.03 mg/mL and path length 1 cm.…”

Section: Materials and Characterizationmentioning

confidence: 99%

“…After the completion of reaction, the precipitated products was just filtered. The confirmation of isolated products was done by spectral techniques such as 1 H, 13 C NMR, IR and mass spectrometry.…”

Section: General Procedures For Synthesis Of 1-h-spiro [Isoindoline-1mentioning

confidence: 99%

“…8 In particular, 3-substituted indolin-2-one derivatives have received extensive biological scrutiny. [9][10][11][12] Recently, extensive and versatile pharmacological properties have been reported for some isatin-derived spiro-2,3-dihydroquinazolinones [13][14][15] (figure 1). In this context, the synthesis of spiro[isoindoline-1,2 -quinazoline]-3, 4 (3 H)-dione is of prime importance.…”

Section: Introductionmentioning

confidence: 99%

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Sulfamic acid as energy efficient catalyst for synthesis of flurophores, 1-H-spiro [isoindoline-1,2′-quinazoline]-3,4′(3′H)-diones

Mane

Pore

2016

J Chem Sci

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An energy efficient synthesis of 1-H-spiro[isoindoline-1,2-quinazoline]-3,4 (3 H)-diones has been expediently accomplished by a reaction of isatin(s) / cyclic ketone and anthranilamide in ethanol at ambient temprature. Excellent yields of the products in short time duration, operational simplicity, and simple work-up procedure are the attractive features of the present protocol. Synthesized 1-H-spiro[isoindoline-1,2quinazoline]-3,4 (3 H)-diones were found to be fluorescent with absorption in UV region (302, 362 nm) and emission in visible region (413-436 nm) with Stokes shift of 44-72 nm.

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Section: Materials and Characterizationmentioning

confidence: 99%

Section: General Procedures For Synthesis Of 1-h-spiro [Isoindoline-1mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Sulfamic acid as energy efficient catalyst for synthesis of flurophores, 1-H-spiro [isoindoline-1,2′-quinazoline]-3,4′(3′H)-diones

Mane

Pore

2016

J Chem Sci

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“…Chiral 3,3'-spirooxindoles are privileged scaffolds that exist in numerous natural products [1] and man-made compounds [2] that display a wide range of pharmacological activities (antitumoral, [3] antitubercular, [4] SIRT 1 [5] and cholinesterase inhibitors). [6] As a result, the synthesis of chiral 3,3'-spirooxindoles have received much attention from chemists for their prominent bioactivities and great challenges involved in the generation of spirocyclic quaternary stereogenic centers.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Asymmetric Construction of 3,3′‐Spirooxindoles Fused with Seven‐Membered Rings by Enantioselective Tandem Reactions

Wang

Shi

Yao

et al. 2014

Chemistry A European J

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The first catalytic asymmetric construction of a spirooxindole scaffold incorporated with a seven-membered benzodiazepine moiety has been established by a three-component (isatin, 1,2-phenylenediamine, cyclohexane-1,3-dione) tandem reaction catalyzed by a chiral phosphoric acid. Structurally complex spirobenzodiazepine oxindoles with one quaternary stereogenic center are obtained in high yield with excellent enantioselectivity (up to 99% yield, enantiomeric ratio>99.5:0.5). This approach takes advantage of organocatalytic asymmetric tandem reactions to efficiently construct the structurally rigid spirobenzodiazepine oxindole architecture with high enantiopurity in a single transformation, which involves a cascade enamine-imine formation/intramolecular Mannich reaction sequence.

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“…Apart from this, dihydroquinazolinones exhibited different biological activities like antibacterial, [7] anticonvaluscent, [8] antiemetic and gastrointestinal motility enhancing agents, [9] IMPDH inhibitors, [10] antifibrillatory activity, [11] antihistaminic action, [12] antiinflammatory, [13,14] antitubercular activities, [15] potential inhibitors of SIRT1, [16] Antileishmanial agents [17] and antitumor agents [18].…”

Section: Introductionmentioning

confidence: 99%

Dihydroquinazolinones as Potential Antiproliferative and Tumor Inhibiting agents

Rangappa¹

2016

OMCIJ

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Spiro heterocycles as potential inhibitors of SIRT1: Pd/C-mediated synthesis of novel N-indolylmethyl spiroindoline-3,2′-quinazolines

Cited by 42 publications

References 29 publications

Sulfamic acid as energy efficient catalyst for synthesis of flurophores, 1-H-spiro [isoindoline-1,2′-quinazoline]-3,4′(3′H)-diones

Sulfamic acid as energy efficient catalyst for synthesis of flurophores, 1-H-spiro [isoindoline-1,2′-quinazoline]-3,4′(3′H)-diones

Catalytic Asymmetric Construction of 3,3′‐Spirooxindoles Fused with Seven‐Membered Rings by Enantioselective Tandem Reactions

Dihydroquinazolinones as Potential Antiproliferative and Tumor Inhibiting agents

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