• Journal of the Korean Magnetic Resonance Society
• /
• v.28 no.3
• /
• pp.15-19
• /
• 2024

1,1'-carbonyldiimidazole (CDI) is a versatile reagent that can be used for synthesizing a variety of organic compounds containing carbonyl functional groups. The reactivity of CDI with two ortho-substituted anilines was tested and characterized with analytic techniques such as NMR, IR, and ESIMS. A reaction of CDI with two equivalents of disubstituted aniline (N¹,N¹-diethylbenzene-1,2-diamine) formed a urea compound, 1,3-bis(2-(diethylamino)phenyl)urea (1). On the other hand, a reaction with one equivalent of mono-substituted aniline (tert-butyl (2-aminophenyl)carbamate) formed a substituted benzimidazolone, tert-butyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate (2). These results demonstrated that a singly substituted aniline prefers an intramolecular ring formation while an N,N-doubly-substituted aniline prefers a urea formation.

• Archives of Pharmacal Research
• /
• v.23 no.2
• /
• pp.116-120
• /
• 2000

Aspirin has been widely used as analgesic and anti-inflammatory drug. Recently, it was elucidated that aspirin have anti-coaggregatory effect in low dose. This study was carried out to investigate the synthesis of aspirin derivatives from aspirin and aromatic compound of antioxidant and its biological activities. Synthesis of aspirin derivatives was prepared by esterification in the presence of 1, 1-carbonyldiimidazole. Biological activities was examined using effect of anti-coagulant on bleeding time, effect of antioxidant and effect of anti-platelet aggregation. As a result, SJ-101 showed strong antioxidative activity and anti-coagulant activity among four compounds. Anti-platelet aggregation of SJ-101 was examined by collagen, ADP, PAF method. SJ-101 exhibited more stronger activity to aspirin at collagen aggregation reaction. These finding demonstrates that SJ-101 is usefull as care drug of aging and old-disease because of its has antioxidant activity, anti-coagulant activity and anti-platelet activity.

• Biotechnology and Bioprocess Engineering:BBE
• /
• v.6 no.4
• /
• pp.293-300
• /
• 2001

A polyrotaxane-biotin conjugate was synthesized and its interaction with streptavidin measured using surface plasmon resonance(SPR) detection. A biodegradable polyrotaxane in which ca, 22 molecules of ${\alpha}$-cyclodextrina(${\alpha}$-CDs) were threaded onto a poly(ethylene oxide) chain(M$\sub$n:4,000) capped with benzyloxycarbonyl-L-phenylalanine was conjugated with a biotin hydorazide and 2-aminoethanol after activing the hydroxyl groups of ${\alpha}$-CDs in the polyrotaxane using N, N'-carbonyldiimidazole. The results of the high-resolution $^1$H-nyclear lmagnetic resonance($^1$H-NMR)spectra and gel permeation chromatography of the conjugate showed that ca, 11 biotin molecules were actually introduced to the polyrotaxane scaffold. An SPR analysis showed that the binding curves of the biotin molecules in the conjugate on the streptavidin-deposited surface changed in a concentration dependent manner, indicating that the biotin in the conjugate was ac-tually recognized by streptavidin. The association equilibrium constant(K$\sub$a/) of the interaction be-tween the conjugate and steptavidin tetramer was of the order 10$\^$7/. These results suggest that polyrotaxane is useful for scaffolds as a polymeric ligand in biomedical fields.

• Bulletin of the Korean Chemical Society
• /
• v.35 no.8
• /
• pp.2381-2384
• /
• 2014

A solid-phase synthetic approach is reported for the synthesis of an ascorbic acid (ASA)-dipeptide conjugate that exhibited enhanced antioxidant activity. The N-terminal amino group of dipeptide (Ala-Ala) on a resin support was first activated by 1,1'-carbonyldiimidazole (CDI), and then reacted with an ASA derivative. The addition of a base, triethylamine (TEA), promoted nucleophilic acylation of ASA derivative and yielded a desired product (ASA-Ala-Ala) with enhanced purity, when cleaved from the resin. Compared to the approach where a C3 hydroxyl group of ASA was first activated with CDI and then reacted with the amino group of dipeptide on the resin, this new approach allowed a significant reduction of a total reaction time from 120 h to 8 h at $25^{\circ}C$. As-prepared ASA-dipeptide conjugate (ASA-Ala-Ala) showed improved antioxidant activity compared to ASA.