Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

Ida, Yoshihiro; Matsubara, Ayaka; Nemoto, Toru; Saito, Manabu; Hirayama, Shigeto; Fujii, H.; Nagase, Hiroshi

doi:10.1016/j.bmc.2012.08.004

Cited by 17 publications

(11 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…General procedures and materials. Compounds 2 44 , 3 45 , 9 46 , 12 47 , 13 48 and PEtG-control 35 High-resolution mass spectrometry (HRMS) was performed using a Finnigan MAT 8400 electron impact (EI) mass spectrometer or Bruker microOTOF 11 electrospray mass spectrometer (ESI).…”

Section: Methodsmentioning

confidence: 99%

“…While the above work demonstrates that diverse stimuli can be used to trigger PEtG depolymerization, for some applications it may be beneficial to develop a versatile end-capping strategy that allows the polymer to respond to multiple stimuli, either individually or simultaneously. To prepare an end-cap responsive to multiple stimuli, the previously reported aniline 9 46 was reacted with chloroformate 4 in the presence of Na 2 CO 3 in THF/H 2 O at 0 °C to functionalize the aniline group selectively, affording compound 10 (Scheme 3). The benzylic alcohol of 10 was then reacted with phosgene to provide the chloroformate-activated end-cap 11.…”

Section: Development Of Multi-responsive End-capsmentioning

confidence: 99%

See 1 more Smart Citation

End-Capping Strategies for Triggering End-to-End Depolymerization of Polyglyoxylates

2016

View full text Add to dashboard Cite

Polymers that undergo end-to-end depolymerization in response to the cleavage of a stimuli-responsive end-cap are promising for diverse applications from drug delivery to responsive coatings and plastics. It is critical that the end-cap is designed to respond to an appropriate stimulus for the application. In the current work, end-caps for triggering the depolymerization of poly(ethyl glyoxylate) (PEtG) were explored. First a phenylboronate, a disulfide, and an azobenzene were utilized to impart redox-responsive properties to PEtG. Then, methoxy-substituted trityl groups were used to provide sensitivity to mild acid. A multi-responsive platform was also introduced, allowing PEtG to respond to multiple stimuli, either simultaneously or independently. Incorporation of a cross-linkable trialkene end-cap enabled the preparation of networks that could subsequently be depolymerized. Finally, high molar mass PEtG could be depolymerized by mechanical stimulation independent of the end-cap. It is anticipated that the versatility in end-capping strategies and potential depolymerization stimuli will not only expand PEtG's utility for different applications, but will also be useful for other classes of end-to-end depolymerizable polymers.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Development Of Multi-responsive End-capsmentioning

confidence: 99%

End-Capping Strategies for Triggering End-to-End Depolymerization of Polyglyoxylates

2016

View full text Add to dashboard Cite

show abstract

“…The residue was purified by silica gel chromatography (10% EtOAc in hexanes) to yield the title compound as a white solid (0.46 g, 79%); 1 H NMR (400 MHz, CDCl 3 ) δ 2.64 (s, 3H), 3.77 (s, 3H), 6.89-7.17 (m, 1H), 7.53 (t, J = 7.7 Hz, 1H), 7.86 (d, J = 7.3 Hz, 1H), 8.46 (d, J = 8.5 Hz, 1H), 11.19 (s, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 29.0, 52.7, 119.6, 121.8, 121.9, 132.1, 135.5, 141.8, 154.8, 202.7 Methyl (2-formyl-5-(trifluoromethyl)phenyl)carbamate (1c). Following the general procedure starting from (2-amino-4-(trifluoromethyl)phenyl)methanol, 23 the title compound was obtained as a white solid (0.65 g, 65%); 1 H NMR (400 MHz, CDCl 3 ) δ 3.84 (s, 3H), 7.31-7.57 (m, 1H), 7.61-8.04 (m, 1H), 8.80 (s, 1H), 9.99 (s, 1H), 10.64 (br s, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 52.7, 115.6 (q, 3 J CF = 4.1 Hz), 118.3 (q, 3 J CF = 4.0 Hz), 122.8 (q, 4 J CF = 1.4 Hz), 122.9 (q, 1 J CF = 236.7 Hz) 136.2 (s), 136.8 (d, 2 J CF = 32.6 Hz), 141. 5, 153.9, 194.4 Methyl (3-chloro-2-formylphenyl)carbamate (1e).…”

Section: General Methodsmentioning

confidence: 99%

A microwave-assisted multicomponent synthesis of substituted 3,4-dihydroquinazolinones

Stevens

Więckowski

et al. 2015

Org. Biomol. Chem.

View full text Add to dashboard Cite

A microwave-assisted, multicomponent protocol for the synthesis of substituted 3,4-dihydroquinazolinones via a novel cascade imine/cyclization/aza-Henry reaction sequence is reported. Starting from o-formyl carbamates, a series of structurally diverse 3,4-dihydroquinazolinones was synthesized via a cyclic iminium ion intermediate in moderate to excellent yields. Notably, the reaction is fast, flexible, simple to perform and tolerates a variety of functional groups.

show abstract

“…The yield proved relatively low, most likely because of the presence of the carboxylic acid moiety. An attempt to obtain 6 by reducing the carboxylic acid of compound 5 following the method introduced by Y. Ida et al [ 18 ] was not successful. The esterification of 5 was carried out in methanol in the presence of SOCl 2 to afford 7 [ 16 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of 1,3-Dideazapurine-Like 7-Amino-5-Hydroxymethyl-Benzimidazole Ribonucleoside Analogues as Aminoacyl-tRNA Synthetase Inhibitors

et al. 2020

View full text Add to dashboard Cite

Aminoacyl-tRNA synthetases (aaRSs) have become viable targets for the development of antimicrobial agents due to their crucial role in protein translation. A series of six amino acids were coupled to the purine-like 7-amino-5-hydroxymethylbenzimidazole nucleoside analogue following an optimized synthetic pathway. These compounds were designed as aaRS inhibitors and can be considered as 1,3-dideazaadenine analogues carrying a 2-hydroxymethyl substituent. Despite our intentions to obtain N1-glycosylated 4-aminobenzimidazole congeners, resembling the natural purine nucleosides glycosylated at the N9-position, we obtained the N3-glycosylated benzimidazole derivatives as the major products, resembling the respective purine N7-glycosylated nucleosides. A series of X-ray crystal structures of class I and II aaRSs in complex with newly synthesized compounds revealed interesting interactions of these “base-flipped” analogues with their targets. While the exocyclic amine of the flipped base mimics the reciprocal interaction of the N3-purine atom of aminoacyl-sulfamoyl adenosine (aaSA) congeners, the hydroxymethyl substituent of the flipped base apparently loses part of the standard interactions of the adenine N1 and the N6-amine as seen with aaSA analogues. Upon the evaluation of the inhibitory potency of the newly obtained analogues, nanomolar inhibitory activities were noted for the leucine and isoleucine analogues targeting class I aaRS enzymes, while rather weak inhibitory activity against the corresponding class II aaRSs was observed. This class bias could be further explained by detailed structural analysis.

show abstract

Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

Cited by 17 publications

References 24 publications

End-Capping Strategies for Triggering End-to-End Depolymerization of Polyglyoxylates

End-Capping Strategies for Triggering End-to-End Depolymerization of Polyglyoxylates

A microwave-assisted multicomponent synthesis of substituted 3,4-dihydroquinazolinones

Synthesis and Biological Evaluation of 1,3-Dideazapurine-Like 7-Amino-5-Hydroxymethyl-Benzimidazole Ribonucleoside Analogues as Aminoacyl-tRNA Synthetase Inhibitors

Contact Info

Product

Resources

About