Synthesis and anti-leukemia evaluation of tetrahydro-4H-pyrano[3,2-c]pyridines and corresponding anti-CD14 monoclonal antibody conjugates

Sun, Chang; Wang, Jing; Chuncheng, PANG; Li, Jing; Xiao, Di

doi:10.1007/s40242-013-3211-7

Cited by 3 publications

(1 citation statement)

References 15 publications

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“…The fused pyrano [3,2-c]pyridine ring skeleton is the most honored heterocycle unit present in many natural products or synthetic products [6][7][8] with a wide spectrum of valuable biological activities, such as antitumor, [9,10] antitubercular, [11,12] cholinesterase inhibitor, [13] and antidiabetic [14] activities. A well-established summary can be given: the biological activities of pyrano [3,2-c]pyridine derivatives rely on the nature of substituents in the pyrano [3,2-c]pyridine ring skeleton.…”

Section: Introductionmentioning

confidence: 99%

One‐pot synthesis of 3‐(sulfonyl)‐5,6,7,8‐tetrahydro‐4H‐pyrano[3,2‐c]pyridines through a cascade Michael/cyclization reaction

Wang

Xiao

et al. 2019

J Chinese Chemical Soc

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In this paper, a straightforward and valid three-component Michael/cyclization reaction of (E)-1-methyl-3-(arylidene)piperidin-4-ones, 2-(sulfonyl)acetonitriles, and aromatic aldehydes was explored for the preparation of potentially biologically active 3-(sulfonyl)-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridines under mild reaction conditions. More diverse 3-(sulfonyl)-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine derivatives were constructed in satisfactory yields (up to 97%). The chemical structure of newly synthesized 3-(sulfonyl)-5,6,7,8-tetrahydro-4H-pyrano[3,2-c] pyridines were identified with 1 H-NMR, 13 C-NMR, and mass spectrometry analysis. The recommendable method features a simple and direct workup, easy access to initial materials, high atom utilization efficiency, high final product yields, and a wide range of substrate adaptability. K E Y W O R D S cyclization, hexahydropyridine, Michael addition, multicomponent reactions, sulfonyl-4H-pyrano [3,2-c]pyridine

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Section: Introductionmentioning

confidence: 99%

One‐pot synthesis of 3‐(sulfonyl)‐5,6,7,8‐tetrahydro‐4H‐pyrano[3,2‐c]pyridines through a cascade Michael/cyclization reaction

Wang

Xiao

et al. 2019

J Chinese Chemical Soc

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Design and synthesis of macrocyclic polyoxazoles

Gao

Han

2014

Chem. Res. Chin. Univ.

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Daylight LED promotes photochemical ring contraction of 2-amine-4H-pyran-3-carbonitriles with consequent loss of their antifungal activity

Silva

Sousa

Ferreira

et al. 2021

Photochem Photobiol Sci

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The initial objective of our work was to synthesize a series of 2-amino-4H-pyran-3-carbonitriles to be tested for their antifungal activities against economically relevant phytopathogenic fungi. Fourteen compounds were prepared in up to 94% yield and shown percentages of Botrytis cinerea inhibition above 70%. Despite the promising biological results, we observed that stock solutions prepared for biological tests showed color changing when kept for a few days on the laboratory bench, under room conditions, illuminated by common LED daylight tubes (4500-6000 k). This prompted us to investigate the possible photo-induced degradation of our compounds. FT-IR ATR experiments evidenced variations in the expected bands for functional of -amino-4H-pyran-3-carbonitriles stored under LED daylight. Following, HPLC-UV analysis showed reductions in the intensity of chromatographic peaks of 2-amino-4H-pyran-3-carbonitriles, and but not for solutions kept in the dark. A solution of (E)-2-amino-8-(4-nitrobenzylidene)-4-(4-nitrophenyl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile underwent 84.4% of conversion after 72 h of exposure to continuous LED daylight in a BOD chamber, and the reaction product was isolated in 36% yield and characterized as (E)-7-cyano-5-(4-nitrobenzylidene)-8-(4-nitrophenyl)bicyclo[4.2.0] oct-1(6)-ene-7-carboxamide (7*). Despite freshly prepared solutions of 2-amino-4H-pyran-3-carbonitriles produced antifungal activities, these solutions lost biological activity when left on the bench for a week. Besides, compound 7* formed from photo-induced degradation of 7 also showed no antifungal activity. With this, we hope to bring two contributions:(1) production of cyclobutenes through photochemical reactions of 2-amino-4H-pyran-3-carbonitriles can be carried out through exposure to simple white LED daylight; (2) biological applications of such 2-amino-4H-pyran-3-carbonitriles may be impaired by their poor photostability.

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Synthesis and anti-leukemia evaluation of tetrahydro-4H-pyrano[3,2-c]pyridines and corresponding anti-CD14 monoclonal antibody conjugates

Cited by 3 publications

References 15 publications

One‐pot synthesis of 3‐(sulfonyl)‐5,6,7,8‐tetrahydro‐4H‐pyrano[3,2‐c]pyridines through a cascade Michael/cyclization reaction

One‐pot synthesis of 3‐(sulfonyl)‐5,6,7,8‐tetrahydro‐4H‐pyrano[3,2‐c]pyridines through a cascade Michael/cyclization reaction

Design and synthesis of macrocyclic polyoxazoles

Daylight LED promotes photochemical ring contraction of 2-amine-4H-pyran-3-carbonitriles with consequent loss of their antifungal activity

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