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Tetrahedron Letters | 2000

Revisit to the sulfonation of pyrroles: is the sulfonation position correct?

Akira Mizuno; Yukiko Kan; Harukazu Fukami; Tomoe Kamei; Kazuo Miyazaki; Shinsuke Matsuki; Yoshiaki Oyama

Abstract Sulfonation of pyrrole and its 1-methyl derivatives with a sulfur trioxide–pyridine complex was found to give 3-sulfonated pyrroles, but not 2-sulfonates as described in textbooks. The replacement of 1-methyl-2-tri- n -butylstannylpyrrole with trimethylsilyl chlorosulfonate, followed by quenching with aq. NaHCO 3 also generated sodium 1-methylpyrrole-3-sulfonate, not 2-sulfonate.


Pharmacochemistry Library | 1995

Background and features of emil, a system for database-aided bioanalogous structural transformation of bioactive compounds

Toshio Fujita; Michihiro Adachi; Miki Akamatsu; Masaaki Asao; Harukazu Fukami; Yoshihisa Inoue; Isao Iwataki; Masaru Kido; Hiroshi Koga; Takamitsu Kobayashi; Izumi Kumita; Kenji Makino; Kengo Oda; Akio Ogino; Masateru Ohta; Fumio Sakamoto; Tetsuo Sekiya; Ryo Shimizu; Chiyozo Takayama; Yukio Tada; Ikuo Ueda; Yoshihisa Umeda; Masumi Yamakawa; Yasunari Yamaura; Hirosuke. Yoshioka; Masanori Yoshida; Masafumi Yoshimoto; Ko Wakabayashi

Abstract Various structural transformation processes observed in a number of past developmental examples of pharmaceuticals and agrochemicals are regarded as being invaluable precedents for the prospective analog design. In certain cases, (sub)structural transformation patterns are interchangeable among various compound series in spite of differences in their pharmacological category. Thus, the patterns extracted with a computer-readable format could be accumulated and integrated as a database for potential “rules” for bioanalogous molecular transformations. EMIL is a system that incorporates the database and a data-processing engine constructed to release “higher-ordered” candidate structures from a “lower-ordered” input structure “automatically”. Conceptual background for the database construction and the procedure for the database collection are presented on the basis of some lead evolution examples among pharmaceutical and agrochemical series of compounds.


Agricultural and biological chemistry | 1977

Syntheses of Ribofuranosyl-2-deoxystreptamines

Harukazu Fukami; Hideki Kohno; Katsuhiko Kitahara; Minoru Nakajima

4-0-, 5-0- and 6-0-β-d-Ribofuranosyl-2-deoxystreptamine derivatives were prepared from 4 (or 6)-O-acetyl-N, N′-dicarbobenzyloxy-2-deoxystreptamine and 2, 3, 5-tri-O-benzoyl-d-ribofuranosyl chloride by a modified Konigs-Knorr reaction. Structures were determined by identification with an authentic sample derived from neomycin for the 5-O-isomer, and by comparison of the Δ [M]CuAm values of their N-acetyl derivatives for the 4-0- and 6-O-isomers.


Agricultural and biological chemistry | 1977

Total Synthesis of Ribostamycin

Harukazu Fukami; Shoji Ikeda; Katsuhiko Kitahara; Minoru Nakajima

Suitably protected 5-O-β-d-ribofuranosyl-2-deoxystreptamine was condensed with protected 2, 6-diamino-2, 6-dideoxy-a-d-glucopyranosyl bromide by a modified Konigs-Knorr reaction to give three condensation products. One of which was confirmed as a ribostamycin derivative. The others were designated as its 6-O-α- and 6-O-β-isomers by the PMR spectra of their free bases and N-acetyl derivatives and by their chemical reactions.


Tetrahedron Letters | 1976

Total synthesis of ribostamycin

Harukazu Fukami; Katsuhiko Kitahara; Minoru Nakajima


Archive | 1998

Pyrrolothiazine and pyrrolothiazepine compounds having serotonin-2 receptor antagonistic and alpha-1-blocking action

Akira Mizuno; Makoto Shibata; Tomoe Kamei; Harukazu Fukami; Norio Inomata


Agricultural and biological chemistry | 1975

Syntheses of a Neobiosamine C Derivative and Its Analogs

Harukazu Fukami; Shoji Ikeda; Hideki Kohno; Minoru Nakajima


Agricultural and biological chemistry | 1975

Syntheses of Neamine and Its Diastereomer; the Condensation of Protected 2,6-Diamino-2,6-dideoxy-α-d-glucopyranosyl Bromide with a 2-Deoxystreptamine Derivative

Hideki Kohno; Harukazu Fukami; Minoru Nakajima


Agricultural and biological chemistry | 1975

Synthesis of a Positional Isomer of Neamine; 5-O-(2, 6-Diacetamido-2, 6-dideoxy-α-D-glucopyranosyl)-N, N'-diacetyl-2-deoxystreptamine

Harukazu Fukami; Haruki Sano; Minoru Nakajima


Archive | 1998

Composes de pyrrolothiazine et pyrrolothiazepine presentant une action antagoniste du recepteur de serotonine-2 et bloquant alpha-1

Akira Mizuno; Makoto Shibata; Tomoe Kamei; Harukazu Fukami; Norio Inomata

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Minoru Nakajima

Darmstadt University of Applied Sciences

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Minoru Nakajima

Darmstadt University of Applied Sciences

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