Kazuya Kawabata

Osaka University, Ōsaka-shi, Osaka-fu, Japan

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Publications (7)27.66 Total impact

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    ABSTRACT: m-Diethynylbenzene macrocycles (DBMs), buta-1,3-diyne-bridged [4(n)]metacyclophanes, have been synthesized and their self-association behaviors in solution were investigated. Cyclic tetramers, hexamers, and octamers of DBMs having exo-annular octyl, hexadecyl, and 3,6,9-trioxadecyl ester groups were prepared by intermolecular oxidative coupling of dimer units or intramolecular cyclization of the corresponding open-chain oligomers. The aggregation properties were investigated by two methods, the (1)H NMR spectra and the vapor pressure osmometry (VPO). Although some discrepancies were observed between the association constants obtained from the two methods, the qualitative view was consistent with each other. The analysis of self-aggregation by VPO revealed unique aggregation behavior of DBMs in acetone and toluene, which was not elucidated by the NMR method. Namely, the association constants for infinite association are several times larger than the dimerization constant, suggesting that the aggregation is enhanced by the formation of dimers (a nucleation mechanism). In polar solvents, DBMs aggregate more strongly than in chloroform due to the solvophobic interactions between the macrocyclic framework and the solvents. Moreover, DBMs self-associate in aromatic solvents such as toluene and o-xylene more readily than in chloroform. In particular, the hexameric DBM having a large macrocyclic cavity exhibits extremely large association constants in aromatic solvents. By comparing the aggregation properties of DBMs with the corresponding acyclic oligomers, the effect of the macrocyclic structure on the aggregation propensity was clarified. Finally, it turned out that DBMs tend to aggregate more readily than the corresponding phenylacetylene macrocycles, acetylene-bridged [2(n)]metacyclophanes, owing to the withdrawal of the electron density from the aromatic rings by the butadiyne linkages which facilitates pi-pi stacking interactions.
    Journal of the American Chemical Society 06/2002; 124(19):5350-64. · 10.68 Impact Factor
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    ABSTRACT: A 51-year-old man presented under a diagnosis of angina pectoris manifesting as exertional chest pain. First coronary angiography showed severe stenosis with ulceration and spontaneous dissection at the proximal right coronary artery and linear dissection-like filling defects extending to the distal right coronary artery. After about 3 months, repeat coronary angiography showed the previously observed stenosis with unclear dissection, and better developed collaterals from the left coronary artery to the right coronary artery showing the linear dissection-like filling defects. The bilateral coronary angiography did not clearly show filling defects. This phenomenon suggested that the collateral flows were related to filling of the defects. Intravascular ultrasonic imaging demonstrated severe atherosclerotic lesions at the proximal right coronary artery, but no dissection in the distal right coronary artery. Percutaneous transluminal coronary angioplasty for the stenosis was performed successfully with a stent. Coronary angiography after the angioplasty showed no collaterals, and the right ventricular branch appeared, suggesting that the linear dissection-like filling defects extending to the distal right coronary artery were due to the collateral flows. Filling defects extending distal to a severe stenosis must be distinguished carefully from coronary dissection.
    Journal of Cardiology 12/2001; 38(5):281-7. · 2.30 Impact Factor
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    ABSTRACT: A 70-year-old female patient presented and ECG with QS patterns and ST elevation in V1-3. Left ventriculography showed severely abnormal wall motion of the anteroseptal similar to a left ventricular aneurysm. Based on previous experience that 201Tl myocardial scintigraphy revealed possible myocardial viability in a patient with left ventricular aneurysm suspected of having apparently no myocardial viability, percutaneous transluminal coronary angioplasty (PTCA) was performed for severe stenosis of the left anterior descending artery. Follow-up images 3 months later showed a remarkable improvement in parietal motility of the left ventricle and recovery of almost normal cardiac function. This case demonstrates that exercise myocardial scintigraphy is useful for diagnosing hibernating myocardium associated with severely abnormal parietal motility, such as left ventricular aneurysm.
    Kaku igaku. The Japanese journal of nuclear medicine 06/2001; 38(3):229-35.
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    ABSTRACT: Butadiyne-bridged [44](2,6)pyridinophane and [46](2,6)pyridinophane derivatives were synthesized, and their heteroassociations with the corresponding metacyclophanes and complexations with organic cations were investigated.
    ChemInform 01/2001; 32(4).
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    ABSTRACT: Butadiyne-bridged [4(4)](2,6)pyridinophane and [4(6)](2, 6)pyridinophane derivatives were synthesized, and their heteroassociations with the corresponding metacyclophanes and complexations with organic cations were investigated.
    Organic Letters 11/2000; 2(21):3265-8. · 6.14 Impact Factor
  • Organic Letters 10/2000; 2(21):3265-3268. · 6.14 Impact Factor
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    ABSTRACT: We synthesized diethynylbenzene macrocycles (DBMs), cyclic oligomers of diethynylbenzene, having functional groups in the periphery of the macrocyclic framework and investigated their self-association properties in solution resulting from π-π stacking interaction. The tetrakis-DBM having hexadecyl ester groups showed dimerization behavior not only in chloroform-d, but also in o-dichlorobenzene-d4.
    Tetrahedron Letters 01/1996; 37(52):9325-9328. · 2.40 Impact Factor