Publications
2014
ACAT2 選択的阻害剤ピリピロペン A の構造簡略型誘導体創製研究
大多和正樹、大村 智、供田 洋、長光 亨 MEDCHEMNEWS, 24(3), 25-31, 2014.
コレステロールアシル転移酵素アイソザイム2 (ACAT2) 阻害活性を有する新規医薬化合物 供田 洋、 大多和 正樹、大村 智、長光 亨. 特願2014-129126
In vitro metabolism of pyripyropene A and ACAT inhibitory activity of its metabolites.
Matsuda, D.; Ohshiro, T.; Ohtawa, M.; Yamazaki, H.; Nagamitsu, T. Tomoda, H. Journal of Antibiotics, 2014. in press.
Synthesis and biological activity of citridone A and its derivatives. Fukuda, T.; Shimoyama, K.; Nagamitsu, T.; Tomoda, H. Journal of Antibiotics, 67(6), 445-450, 2014.
Effects of pre- and post- natal treatment with KRN633, an inhibitor of vascular endothelial growth factor recepter tyrosine kinase, on retinal vascular development and patterning in mice. Morita, A.; Nakahara, T.; Abe, N.; Kurauchi, Y.; Mori, A.; Sakamoto, K.; Nagamitsu, T.; Ishii, K. Experimental Eye Research, 120, 127-137, 2014.
Regioselective Mono-deprotection of Di-tert-butylsilylene acetal derived from 1,3-diol with ammonium fluoride. Ohtawa, M.; Tomoda, H.; Nagamitsu, T. Bulletin of the Chemical Society of Japan, 87(1), 113-118, 2014.
2013
KRN633, an inhibitor of vascular endothelial growth factor receptor tyrosine kinase, induces intrauterine growth restriction in mice. Abe, N.; Nakahara, T.; Morita, Y.; Mori, A.; Sakamoto, K.; Nagamitsu, T.; Ishii, K. Birth Defects Research Part B: Developmental and Reproductive Toxicology, 98(4), 297-303, 2013.
新規脂質異常症予防治療薬を指向した ACAT2 選択的阻害剤ピリピロペン A の構造活性相関研究
大多和正樹、大村 智、供田 洋、長光 亨 有機合成化学協会誌, 8(8), 830-843, 2013.
Synthesis and structure-activity relationship of pyripyropene A derivatives as potent and selective Acyl-CoA:cholesterol acyltransferase 2 (ACAT2) inhibitors: Part 3. Ohtawa, M.; Yamazaki, H.; Matsuda, D.; Ohshiro, T.; Rudel, L. L.; Omura, S.; Tomoda, H.; Nagamitsu, T. Bioorganic & Medicinal Chemistry Letters, 23(13), 3798-3801, 2013.
Synthesis and structure-activity relationship of pyripyropene A derivatives as potent and selective Acyl-CoA:cholesterol acyltransferase 2 (ACAT2) inhibitors: Part 2. Ohtawa, M.; Yamazaki, H.; Matsuda, D.; Ohshiro, T.; Rudel, L. L.; Omura, S.; Tomoda, H.; Nagamitsu, T. Bioorganic & Medicinal Chemistry Letters, 23(9), 2659-2662, 2013.
Synthesis and structure-activity relationship of pyripyropene A derivatives as potent and selective Acyl-CoA:cholesterol acyltransferase 2 (ACAT2) inhibitors: Part 1. Ohtawa, M.; Yamazaki, H.; Ohte, S.; Matsuda, D.; Ohshiro, T.; Rudel, L. L.; Omura, S.; Tomoda, H.; Nagamitsu, T. Bioorganic & Medicinal Chemistry Letters, 23(5), 1285-1287, 2013.
Role of vascular endothelial growth factor in maintenance of pregnancy in mice. Wada, Y.; Ozaki, H.; Abe, N.; Mori, A.; Sakamoto, K.; Nagamitsu, T.; Nakahara, T.; Ishii, K. Endocrinology, 154(2), 900-910, 2013.
2012
Stereoselective total synthesis of atpenins A4 and B, harzianopyridone, and NBRI23477 B. Ohtawa, M.; Sugiyama, K.; Hiura, T.; Izawa, S.; Shiomi, K.; Omura, S.; Nagamitsu, T. Chemical & Pharmaceutical Bulletin, 60(7), 898-906, 2012.
Potentiation of bleomycin in Jurket cells by fungal pycnidione. Kaneko, M.;Matsuda, D.; Ohtawa, M.; Fukuda, T.;Nagamitsu, T.; Yamori, T.; Tomoda, H. Biological & Pharmaceutical Bulletin, 35(1), 18-21, 2012.
2011
Total synthesis and absolute configuration of avenolide, extracellular factor in Streptomyces avermitilis. Uchida, M.; Takamatsu, S.; Arima, S.; Miyamoto, T. K; Kitani, S.; Nihara, T.; Ikeda, H.; Nagamitsu, T. Journal of Antibiotics, 64(12), 781-787, 2011.
Avenolide, a Streptomyces hormone controlling antibiotic production in Streptomyces avermitilis. Kitani, S.; Miyamoto, T. K; Takamatsu, S.; Herawati, E.; Iguchi, H.; Noshitomi, K.; Uchida, M.; Nagamitsu, T.; Omura, S.; Ikeda, H.; Nihara, T. Proceedings of the National Academy of Sciences of the United States of America, 108(39), 16410-16415, 2011.
Total Synthesis of Pyripyropene A. Odani, A.; Ishihara, K.; Ohtawa, M.; Tomoda, H.; Omura, S.; Nagamitsu, T. Tetrahedron, 67(42), 8195-8203, 2011.
Total Synthesis of Citridone A. Miyagawa, T.; Nagai, K.; Yamada, A.; Sugihara, Y.; Fukuda, T.; Fukuda, T.; Uchida, R.; Tomoda, H.; Omura, S.; Nagamitsu, T. Organic Letters, 13(5), 1158-1161, 2011.
2010
ACAT2阻害活性を有する代謝酵素に安定なピリピロペン誘導体 供田洋、長光亨、松田大介、大城太一、大多和正樹、大村智. 特願2010-82784
ACAT2阻害活性を有する水酸基含有ピリピロペン誘導体 供田洋、長光亨、松田大介、大城太一、大多和正樹、大村智. PCT/JP2010/060461
Effect of KRN633, an inhibitor of vascular endothelial growth factor receptor-2 tyrosine kinase, on vascular development of placenta and fetus of mid pregnancy in mice. Wada, Y.; Ozaki, H.; Abe, N.; Nagamitsu, T.; Ohta, H.; Nakahara, T.; Ishii, K. Journal of Pharmacological Sciences, 112(3), 290-298, 2010.
Structure and total synthesis of fungal calpinactam, a new antimycobacterial agent. Koyama, N.; Kojima, S.; Fukuda, T.; Nagamitsu, T.; Yasuhara, T.;Ōmura, S.; Tomoda, H. Organic Letters, 12(3), 432-435, 2010.
2009
ACAT2阻害活性を有するピリピロペン誘導体(Pyripyropene derivatives having ACAT2-inhibiting activity) 供田洋、長光亨、大村智、Lawrence Lee Rudel. PCT/JP2008/073501,
WO/2009/081957
9-(2-C-Cyano-2-deoxy-b-D-arabino-pentofuranosyl)guanine, a potential antitumor agent B-lymphoma infected with Kaposi’s sarcoma-associated herpesvirus. Ichikawa, S.; Ohtawa, M.; Teishikata, Y.; Yamada, K.; Fujimuro, M.; Yokosawa, H.; Matsuda, A. Nucleic Acids Symposium Series, 53(1), 95-96, 2009.
Enantioselective total synthesis of atpenin A5. Ohtawa, M.; Ogihara, S.; Sugiyama, K.; Shiomi, K.; Harigaya, Y.; Nagamitsu, T.; Ōmura, S. Journal of Antibiotics, 62(6), 289-294, 2009.
Total synthesis of amidepsine B and revision of its absolute configuration. Nagamitsu, T.; Marumoto, K.; Nagayasu, A.; Fukuda, T.; Arima, S.; Uchida, R.; Ohshiro, T.; Harigaya, Y.; Ōmura, S. Journal of Antibiotics, 62(2), 69-74, 2009.
Iridoid glucosides from leaves and stem barks of Parkia javanica. Dinda, B.; Mohanta, B. S.; Debnath, S.; Ghosh, B.; Arima, S.; Sato, N.; Harigaya, Y. Journal of Asian Natural Products Research, 11, 229-235, 2009.
A mild and expedient one-pot synthesis of substituted benzimidazoles in water using a phase-transfer catalyst. Chakrabarty, M.; Karmakar, S.; Mukherjee, R.; Arima, S.; Sato, N.; Harigaya, Y. Monatshefte für chemie, 140(4), 375-380, 2009.
Reaction of isatins with active methylene compounds on neutral alumina: formation of Knoevenagel condensates and other interesting products. Chakrabarty, M.; Mukherjee, R.; Arima, S.; Harigaya, Y. Heterocycles, 78(1), 139-148, 2009.
Expeditious reaction of ninhydrin with active methylene compounds on montmorillonite K10 clay. Chakrabarty, M.; Mukherji, A.; Arima, S.; Harigaya, Y.; Pilet, G. Monatshefte für chemie, 140(2), 189-197, 2009.
2008
Total synthesis of salinosporamide A. Fukuda, T.; Sugiyama, K.; Arima, S.; Harigaya, Y.; Nagamitsu, T.; Ōmura, S. Organic Letters, 10(19), 4239-4242, 2008.
Selectivity of pyripyropene derivatives in inhibition toward Acyl-CoA:cholesterol acyltransferase 2 isozyme. Ohshiro, T.; Ohte, S.; Matsuda, D.; Ohtawa, M.; Nagamitsu, T.; Sunazuka, T.; Harigaya, Y.; Rudel, L. L.; Ōmura, S.; Tomoda, H. Journal of Antibiotics, 61(8), 503-508, 2008.
The total synthesis and biological evaluation of nafuredin-γ and its analogues. Nagamitsu, T.; Takano, D.; Seki, M.; Arima, S.; Ohtawa, M.; Shiomi, K.; Harigaya, Y.; Ōmura, S. Tetrahedron, 65(35), 8117-8127, 2008.
An expedient, regioselective synthesis of novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their anticancer potencial. Chakrabarty, M.; Kundu, T.; Arima, S.; Harigaya, Y. Tetrahedron, 64(28), 6711-6723, 2008.
Iridoid glucoside and sterol galactoside from Mussaenda macrophylla. Dinda, B.; Majumder, S.; Arima, S.; Sato, N.; Harigaya, Y. Journal of Natural Medicine, 62(4), 447-451, 2008.
Total synthesis of salinosporamide A. Fukuda, T.; Sugiyama, K.; Arima, S.; Harigaya, Y.; Nagamitsu, T.; Ōmura, S. Organic Letters, 10(19), 4239-4242, 2008.
Selectivity of pyripyropene derivatives in inhibition toward Acyl-CoA:cholesterol acyltransferase 2 isozyme. Ohshiro, T.; Ohte, S.; Matsuda, D.; Ohtawa, M.; Nagamitsu, T.; Sunazuka, T.; Harigaya, Y.; Rudel, L. L.; Ōmura, S.; Tomoda, H. Journal of Antibiotics, 61(8), 503-508, 2008.
The total synthesis and biological evaluation of nafuredin-γ and its analogues. Nagamitsu, T.; Takano, D.; Seki, M.; Arima, S.; Ohtawa, M.; Shiomi, K.; Harigaya, Y.; Ōmura, S. Tetrahedron, 65(35), 8117-8127, 2008.
An expedient, regioselective synthesis of novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their anticancer potencial. Chakrabarty, M.; Kundu, T.; Arima, S.; Harigaya, Y. Tetrahedron, 64(28), 6711-6723, 2008.
Iridoid glucoside and sterol galactoside from Mussaenda macrophylla. Dinda, B.; Majumder, S.; Arima, S.; Sato, N.; Harigaya, Y. Journal of Natural Medicine, 62(4), 447-451, 2008.
2007
9-(2-C-Cyano-2-deoxy-b-D-arabino-pentofuranosyl)guanine, a potential antitumor agent B-lymphoma infected with Kaposi’s sarcoma-associated herpesvirus. Ohtawa, M.; Ichikawa, S.; Teishikata, Y.; Fujimuro, M.; Yokosawa, H.; Matsuda, A. Journal of Medicinal Chemistry, 50(9), 2007-2010, 2007.
One-pot formation of functionalized 2-piperidinones from arylidenecyanoacetates and methanolic ammonia via tandem reactions. Chakrabarty, M.; Karmakar, S.; Arima, S.; Harigaya, Y. Heterocycles, 73, 795-804, 2007.
A Keggin heteropoly acid as an efficient catalyst for an expeditious, one-pot synthesis of 1-methyl-2-(hetero)arylbenzimidazoles. Chakrabarty, M.; Mukherji, A.; Mukherjee, R.; Arima, S.; Harigaya, Y. Tetrahedron Letters, 48(30), 5239-5242, 2007.
Chemical constituents of evolvulus nummularius. Dinda, B.; Ghosh, B. Arima, S.; Sato, N.; Harigaya, Y. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 46B(3), 492-498, 2007.
Total synthesis of borrelidin. Nagamitsu, T.; Takano, D.; Marumoto, K.; Fukuda, T.; Furuya, K.; Otoguro, K.; Takeda, K.; Kuwajima, I.; Harigaya, Y.; Ōmura, S. Journal of Organic Chemistry, 72(8), 2744-2756, 2007.
2006
An expeditious approach to Knoevenagel condensation of Meldrum's acid on natural alumina using microwave irradiation. Chakrabarty, M.; Mukherjee, R.; Chakrabarty, M.; Arima, S.; Harigaya, Y. Letters in Organic Chemistry, 3(11), 868-871, 2006.
A new bis-iridoid glucoside from Mussaenda incana. Dinda, B.; Debnath, S.; Majumder, S.; Arima, S.; Sato, N.; Harigaya, Y. Chinese Chemical Letters, 17(10), 1331-1334, 2006.
Phosphoric acid-on-silica gel: a green catalyst for the synthesis of symmetrical bis(indolyl)alkanes. Chakrabarty, M.; Mukherjee, R.; Mukherji, A.; Arima, S.; Harigaya, Y. Heterocycles, 68(8), 1659-1668, 2006.
Structure elucidation of fungal sespendole, an inhibitor of lipid droplet synthesis in macrophages. Uchida, R.; Kim, Y. -P.; Nagamitsu, T.; Tomoda, H.; Ōmura, S. Journal of Antibiotics, 59(6), 338-344, 2006.
Application of sulfamic acid as an eco-friendly catalyst in an expedient synthesis of benzimidazoles. Chakrabarty, M.; Karmakar, S.; Mukherji, A.; Arima, S.; Harigaya, Y. Heterocycles, 68(5), 967-974, 2006.
A new catalytic application of a Keggin acid in the synthesis of symmetrical bis(indolyl) alkanes. Chakrabarty, M.; Mukherji, A.; Karmakar, S.; Arima, S.; Harigaya, Y. Heterocycles, 68(2), 331-338, 2006.
Iridoid glucosides from Wendlandia tinctoria roots. Dinda, B.; Debnath, S.; Arima, S.; Sato, N.; Harigaya, Y. Chemical & Pharmaceutical Bulletin, 54(7), 1030-1033, 2006.
Preparation of 7-halo-indoles by thallation of N-formylindoline and their attempted use for synthesis of the right-hand segment of chloropeptin. Yamada, Y.; Arima, S.; Okada, C.; Akiba, A.; Kai, T.; Harigaya, Y. Chemical & Pharmaceutical Bulletin, 54(6), 788-794, 2006.
Antimicrobial C-glucoside from aerial parts of Diospyros nigra. Dinda, B.; Bhattacharya, A.; De, U. C.; Arima, S.; Takayanagi, H.; Harigaya, Y. Chemical & Pharmaceutical Bulletin, 54(5), 679-681, 2006.
2005
Total synthesis of borrelidin. Nagamitsu, T.; Harigaya, Y.; Ōmura, S. Proceedings of the Japan Academy, Series B: Physical and Biological Sciences, 81(7), 244-256, 2005.
Synthesis of linear tripeptides for right-hand segments of complestatin. Yamada, Y.; Akiba, A.; Arima, S.; Okada, C.; Yoshida, K.; Itoh, F.; Kai, T.; Satou, T.; Takeda, K.; Harigaya, Y. Chemical & Pharmaceutical Bulletin, 53(10), 1277-1290, 2005.
Chemical constituents of Mussaenda incana. Dinda, B.; Debnath, S.; Majumder, S.; Arima, S.; Sato, N.; Harigaya, Y. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 44B(11), 2362-2366, 2005.
Triterpenoids from Bignonia unguiscati roots. Dinda, B.; Utpal, C. D.; Arima, S.; Sato, N.; Harigaya, Y. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 44B(8), 1735-1739, 2005.
Azithromycin inhibits the formation of flagellar filaments without suppressing flagellin synthesis in Salmonella enterica serovar Typhimurium. Matsui, H.; Eguchi, M.; Ohsumi, K.; Nakamura, A.; Isshiki, Y.; Sekiya, K.; Kikuchi, Y.; Nagamitsu, T.; Masuma, R.; Sunazuka, T.; Ōmura, S. Antimicrobial Agents and Chemotherapy, 49(8), 3396-3403, 2005.
An expedient, regioselective synthesis of 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]indoles. Chakrabarty, M.; Kundu, T.; Arima, S.; Harigaya, Y. Tetrahedron Letters, 46(16), 2865-2868, 2005.
A γ-lactone form nafuredin, nafuredin-γ, also inhibits helminth complex I. Shiomi, K.; Ui, H.; Suzuki, H.; Hatano, H.; Nagamitsu, T.; Takano, D.; Miyadera, H.; Yamashita, T.; Kita, K.; Miyoshi, H.; Harder, A.; Tomoda, H.; Ōmura, S. Journal of Antibiotics, 58(1), 50-55, 2005.
Macrolides with promotive activity of monocyte to macrophage differentiation. Yoshida, K.; Sunazuka, T.; Nagai, K.; Sugawara, A.; Cho, A.; Nagamitsu, T.; Harigaya, Y.; Otoguro, K.; Akagawa, K.; Ōmura, S. Journal of Antibiotics, 58(1), 79-81, 2005.
2004
Phytochemical investigation of gomphrena globosa aerial parts. Dinda, B.; Ghosh, B. Arima, S.; Sato, N.; Harigaya, Y. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 43B(10), 2223-2227, 2004.
Total synthesis of (-)-Borrelidin. Nagamitsu, T.; Takano, D.; Fukuda, T.; Otoguro, K.; Kuwajima, I.; Harigaya, Y.; Ōmura S. Organic Letters, 6(11), 1865-1867, 2004.
2003
Total synthesis of nafuredin-γ, aγ-lactone related to nafuredin with selective inhibitory activity against NADH-fumarate reductase. Nagamitsu, T.; Takano, D.; Shiomi, K.; Ui, H.; Yamaguchi, Y.; Masuma, R.; Harigaya, Y.; Kuwajima, I.; Ōmura, S. Tetrahedron Letters, 44(34), 6441-6444 2003.
Steroid and nitrophenol esters from Bignonia unguis-cati roots. Dinda, B.; De, U. C.; Achari, B.; Arima. S.; Sato, N.; Harigaya, Y. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 42B(6), 1514-1518, 2003.
Mechanism of activity enhancement of azole antifungal agents by new eruthromycin derivative. Ōmura, S.; Arai, M.; Satoh, K.; Nagamitsu, T.; Nagai, K.; Sunazuka, T.; Tomoda, H. Journal of Antibiotics, 57, 96-100, 2003.
2002
Convenient synthesis of 7' and 6'-bromo-D-tryptophan and their derivatives by enzymatic optical resolution using D-aminoacylase. Konda-Yamada, Y.; Okada, C.; Yoshida, K.; Umeda, Y.; Arima, S.; Sato, N.; Kai, T.; Takayanagi, H.; Harigaya, Y. Tetrahedron, 58(39), 7851-7861, 2002.
Study of the reactions of four indolic 1-azadienes with a few enoic, ynoic, and azo dienophiles. Chakrabarty, M.; Sarkar, S.; Khasnobis, S.; Harigaya, Y.; Sato, N.; Arima, S. Synthetic Communications, 32(15), 2295-2306, 2002.
2001
Absolute configuration of nafuredin, a new specific NADH-fumarate reductase inhibitor. Takano, D.; Nagamitsu, T.; Ui, H.; Shiomi, K.; Yamaguchi, Y.; Masuma, R.; Kuwajima, I.; Ōmura, S. Tetrahedron Letters, 42(16), 3017-3020, 2001.
Total synthesis of nafuredin, a selective NADH-fumarate reductase inhibitor. Takano, D.; Nagamitsu, T.; Ui, H.; Shiomi, K.; Yamaguchi, Y.; Masuma, R.; Kuwajima, I.; Ōmura, S. Organic Letters, 3(15), 2289-2291, 2001
Nafuredin, a novel inhibitor of NADH-fumarate reductase, produced by Aspergillus niger FT-0554. Ui, H.; Shiomi, K.; Yamaguchi, Y.; Masuma, R.; Nagamitsu, T.; Takano, D.; Sunazuka, T.; Namikoshi, M; Ōmura, S. Journal of Antibiotics, 54, 234-238, 2001.
An anthelmintic compound, nafuredin, shows selective inhibition of complex I in helminth mitochondria. Ōmura, S.; Miyadera, H.; Ui, H.; Shiomi, K.; Yamaguchi, Y.; Masuma, R.; Nagamitsu, T.; Takano, D.; Sunazuka,T.; Harder, A.; Kolbl, H.; Namikoshi, M.; Miyoshi, H.; Sakamoto, K.; Kita, K. Proceedings of the National Academy of Sciences of the United States of America, 98, 60-62, 2001.