• Proceedings of the PSK Conference
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• 2002.10a
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• pp.366.2-366.2
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• 2002

In an effort to search for the chemically and enzymatically stable carbonucleoside. we designed ［1'-fluoro-2', 2'-bis-(hydroxymethyl) cyclopropyl methyl］ purines. The underlying concept for our design is to seek relatively conformationally-locked compound with minimal structural disturbance from acyclic carbonucleoside such as acyclovir or penciclovir. To meet such a requirement. we need to introduce cyclopropane and fluorine moiety. (omitted)

• Korean Journal of Soil Science and Fertilizer
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• v.42 no.2
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• pp.139-143
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• 2009

We examined the vertical distribution of specific microbial groups and the patterns of microbial community structure within the soil profile using phospholipid fatty acid (PLFA). Samples were collected from the soil surface down to 15 cm in depth from paddy and upland fields located in Daegu, Korea. The two fields have been fertilized with only chemical fertilizers N, P, K for 33 years. Principal component analysis of the PLFA signatures indicated that the composition of the soil microbial communities changed significantly with the cultivation practices and soil depth, suggesting that cultivation practices of paddy and upland fields had more significant influence on soil microbial community than the soil depth did. The soil microbial communities changed more drastically with soil depth in upland field than in paddy field, with making thicker soil surface in paddy field in terms of soil microbial community. The ratios of cyclopropyl/monoenoic precursors and total saturated/total monounsaturated fatty acids increased with soil depth, suggesting that the deeper soil horizons are more carbon-limited and anaerobic than surface soil. The community analysis using PLFAs as biomarkers revealed that Gram-positive bacteria and actinomycetes tended to increase in proportional abundance with increasing soil depth, while the abundance of Gram-negative bacteria and fungi were highest at the soil surface and substantially lower in the subsurface.

• Applied Chemistry for Engineering
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• v.7 no.6
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• pp.1096-1104
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• 1996

In order to synthesize a new antibacterial and antitumor agents, we have prepared new analogues pteroic acid(13a, 13b), which means C-9 position of pteroic acid has been replaced by norfloxacin(8) or ciprofloxacin(9) and amino group of C-2 position by $CH_3$. These derivatives were synthesized coupling at N-4 piperazine of norfloxacin and ciprofloxacin with 2-amino-3-cyano-5-chloromethylpyrazine(20) provided 1-alkyl(ethyl, cyclopropyl)-6-fluoro-1,4-dihydro-4-oxo-7-[[4-N-(2-amino-3-cyanopyrazin-5-yl)methyl]piperazin-1-yl]-3-quinoline-carboxylic acid(12a, 12b). It was then cyclized with acetamidine. HCI to obtain new analogues of C-2 desaminomethylpteroic acid(13a, 13b) in yield of 76.2% and 82.8 % respectively. These compounds were tested in vitro on antibacterial activity against Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa ATCC9027. In general, these synthesized compounds(13a, 13b) showed less potent activities than those of norfloxacin.

• Journal of the Korean Chemical Society
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• v.50 no.4
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• pp.291-297
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• 2006

The equilibrium structures, relative energies and NBO analyses for the possible conformations and transition states which can exist on the internal rotation of CPDFB and CPCFB molecules have been investigated using DFT and ab initio methods with various basis sets. The interaction between bonding orbital ((C1-C3, C2-C3)) and antibonding orbital (n*(B9) and *(B9-Cl11)) was the main characteristic hyperconjugation in both molecules. In addition, the stabilization energy of CPDFB was 6.63kcal/mol and that of CPCFB was 6.97(E-form)/6.79(Z-form) kcal/mol for each conformation. The rotational barriers by internal rotation of BF2- and BFCl- functional groups were evaluated to be 5.3~6.7kcal/mol and 5.7~6.5kcal/mol respectively, which showed good agreement with the experimental values reported by previous dynamic NMR study. Finally, Z-form was more stable than E-form by 0.2 kcal/mol in CPCFB molecule and therefore Z-form was confirmed as global minimum.

• YAKHAK HOEJI
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• v.39 no.4
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• pp.351-359
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• 1995

The in vitro and in vivo antibacterial activities of DWQ-217 (1-cyclopropyl-6-fluoro-8-chloro-7-(3-amino-4-methylthiomethylpyrrolidinyl )-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid) were compared with those of ciprofloxacin (CPFX) and vancomycin(VCM). DWQ-217 was superior to those of CPFX and VCM against gram positive bacteria. DWQ-217 showed excellent activity against MRSA (MIC of methicillin; $\geq$12.5 $\mu\textrm{g}$/ml), MIC$_{90}$=0.013. DWQ-217 possessed strong bactericidal action against gram positive and gram negative strains by MIC/MBC test and killing curve. DWQ-217 and CPFX were administered orally and subcutaneously to mice infected systematically with S. aureus and S. pyogenes, DWQ-217 was $\geq$5-16 fold(p.o.) and $\geq$3-5 fold(s.c.) more active than CPFX.

• Journal of Integrative Natural Science
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• v.10 no.4
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• pp.209-215
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• 2017

CXC chemokine receptor 2 (CXCR2) is a prominent chemokine receptor on neutrophils. CXCR2 antagonist may reduce the neutrophil chemotaxis and alter the inflammatory response because the neutrophilic inflammation in the lung diseases is found to be largely regulated through CXCR2 receptor. Hence, in the present study, Topomer based Comparative Molecular Field Analysis (Topomer CoMFA) was performed on a series of CXCR2 antagonist named pyrimidine-5-carbonitrile-6-alkyl derivatives. The best Topomer COMFA model was obtained with significant cross-validated correlation coefficient ($q^2$ = 0.487) and non cross-validated correlation coefficients ($r^2$ = 0.980). The model was evaluated with six external test compounds and its $r^2{_{pred}}$ was found to be 0.616. The steric and electrostatic contribution map show that presence of bulkier and electropositive group around cyclopropyl ring may contribute more for improving the biological activities of these compounds. The generated Topomer CoMFA model could be helpful for future design of novel and structurally related CXCR2 antagonists.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.44 no.2
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• pp.176-179
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• 1999

Trinexapac-ethyl[ 4-(cyclopropyl- $\alpha$ -hydroxy-methylene)-3,5-dioxocyclohexane carboxylic acid ethylester] is a growth-retardant for plants by inhibiting a key step in biosynthesis of GA. A treatment of trinexapacethyl generally induces a reduction in vegetative growth and also inhibits heading. In addition, the trinexapacethyl was known to enhance the freeze-tolerance in annual bluegrass, however, the mechanism is not known yet. One possible reason for the enhanced freeze-tolerance may be the antifreeze protein known to be accumulated in intercellular space of the leaf during cold acclimation. In order to see the possible in-duction of the synthesis of antifreeze proteins by trinexacpacethyl, the apoplastic proteins extracted from Kentucky bluegrass treated with trinexapacethyl were analyzed by SDS-PAGE and the presence of the antifreeze protein was observed. In addition, western analysis showed the identity of the protein induced by both a cold acclimation and a trinexapacethyl treatment. It appears that an enhanced freeze-tolerance of the turf grass by trinexapacethyl is due to the synthesis and/or accumulation of the antifreeze protein similar to the enhanced freeze tolerance induced by cold acclimation.

• Archives of Pharmacal Research
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• v.11 no.4
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• pp.292-300
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• 1988

Metabolism of tranylcypromine (TCP) in rat liver microsomes was studied in vitro using fortified microsomal preparations. As well as unlabeled TCP, two deuterium labeled analogs, TCP-phenyl-$d_{5}$ and TCP-cyclopropyl-$d_{2}$ were used and GC/MS employed which was then metabolized to cinnamaldehyde and hydrocinnamyl alcohol. Schiff bases of TCP with hydrocinnamaldehyde and acetaldehyde were detected and possibility of the metabolic formation of N-ethylidene TCP was proposed. In addition, acetophenone (benzoylacetic acid), benzaldehyde, benzoic acid, and benzyl alcohol were detected as the metabolites. Chemical decomposition studies suggested that parts of the oxidized products might be derived by air oxidation processes. A potential metabolite assumed to be N-ethylidene-1, 2-dihydroxy-3-phenylpropanamine oxide was also detected.

• Bulletin of the Korean Chemical Society
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• v.10 no.2
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• pp.132-133
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• 1989

To probe the geometrical effects of cyclopropyl moiety on the stabilization of an adjacent cation center, chemical shift of 2-p-fluorophenyl-8,9-dehydro-2-adamantyl cation (3) was compared with that of 5-p-fluorophenyl-2,4-dehydro-5-homoadamantyl cation (4). Difference between the chemical shift of 8,9-dehydro-2-adamantyl cation 3 and that of 2,4-dehydro-5-adamantyl cation 4 is 5.1 ppm (${\Delta}{\Delta}{\delta}$). We conclude, therefore, that ion 3 is about 3.82 kcal more stadble than ion 4 of which rigid carbon skeleton requires significant distortion of the cyclopropane ring from the ideal bisected conformation. The energy difference between these cations can be calculated by Taft-Relationship$^8$ on the basis of chemical shift.

• Bulletin of the Korean Chemical Society
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• v.17 no.3
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• pp.269-273
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• 1996

Alkyl halides were reduced to the corresponding alkanes by the homonuclear bridging hydride, (μ-H)[(η5-MeCp)Mn(CO)2]2-PPN+ in THF at the elevated temperatures (40-60 ℃) under the pseudo first order reaction conditions where excess of alkyl halide was employed under nitrogen atmosphere. The reaction is of overall second order; first order with respect to [bridging hydride] and first order with respect to [alkyl halide] with the activation parameters, ΔH≠=28.93 kcal/mol and ΔS≠=17.95 e.u. The kinetic data, the ESR evidence and the reaction with cyclopropyl canbinyl bromide ensure that two possible reaction pathways are operable in this reaction: (1) concerted mechanism, and (2) single electron transfer pathway are in competition leading to the same product, the corresponding alkane.