Late-Stage Derivatization of Oleanolic Acid-Based Anti-HIV-1 Compounds
Chem Pharm Bull (Tokyo). 2024;72(3):330-335. doi: 10.1248/cpb.c23-00891.ABSTRACTA 12-keto-type oleanolic acid derivative (4) has been identified as a potent anti-human immunodeficiency virus type-1 (HIV-1) compound that demonstrates synergistic effects with several types of HIV-1 neutralizing antibodies. In the present study, we used a common key synthetic intermediate to carry out the late-stage derivatization of an anti-HIV compound based on the chemical structure of a 12-keto-type oleanolic acid derivative. To execute this strategy, we designed a diketo-type oleanolic acid derivative (5) for chemoselective transformatio...
Source: Chemical and Pharmaceutical Bulletin - March 24, 2024 Category: Drugs & Pharmacology Authors: Reon Takeuchi Junko Fujimoto Yoshinori Taguchi Ryuji Ide Ryuji Kyan Kohei Sato Nobuyuki Mase Masaru Yokoyama Shigeyoshi Harada Tetsuo Narumi Source Type: research

Synthesis of 2-Substituted Indoles via Migration Reaction of 3-Substituted Indoles with Triflic Acid
This study showcases the 1,2-migration reactions of alkyl and aryl groups on the indole molecule. Trifluoromethanesulfonic acid effectively facilitates the migration of the substituent from C3- to C2-position of the indole structure. The resulting C2-substituted indoles offer a valuable pathway for the synthesis of natural products and medicinal compounds.PMID:38522900 | DOI:10.1248/cpb.c23-00792 (Source: Chemical and Pharmaceutical Bulletin)
Source: Chemical and Pharmaceutical Bulletin - March 24, 2024 Category: Drugs & Pharmacology Authors: Kosuke Nakashima Yuka Kudo Yasuyuki Matsushima Shin-Ichi Hirashima Tsuyoshi Miura Source Type: research

Late-Stage Derivatization of Oleanolic Acid-Based Anti-HIV-1 Compounds
Chem Pharm Bull (Tokyo). 2024;72(3):330-335. doi: 10.1248/cpb.c23-00891.ABSTRACTA 12-keto-type oleanolic acid derivative (4) has been identified as a potent anti-human immunodeficiency virus type-1 (HIV-1) compound that demonstrates synergistic effects with several types of HIV-1 neutralizing antibodies. In the present study, we used a common key synthetic intermediate to carry out the late-stage derivatization of an anti-HIV compound based on the chemical structure of a 12-keto-type oleanolic acid derivative. To execute this strategy, we designed a diketo-type oleanolic acid derivative (5) for chemoselective transformatio...
Source: Chemical and Pharmaceutical Bulletin - March 24, 2024 Category: Drugs & Pharmacology Authors: Reon Takeuchi Junko Fujimoto Yoshinori Taguchi Ryuji Ide Ryuji Kyan Kohei Sato Nobuyuki Mase Masaru Yokoyama Shigeyoshi Harada Tetsuo Narumi Source Type: research

Synthesis of 2-Substituted Indoles via Migration Reaction of 3-Substituted Indoles with Triflic Acid
This study showcases the 1,2-migration reactions of alkyl and aryl groups on the indole molecule. Trifluoromethanesulfonic acid effectively facilitates the migration of the substituent from C3- to C2-position of the indole structure. The resulting C2-substituted indoles offer a valuable pathway for the synthesis of natural products and medicinal compounds.PMID:38522900 | DOI:10.1248/cpb.c23-00792 (Source: Chemical and Pharmaceutical Bulletin)
Source: Chemical and Pharmaceutical Bulletin - March 24, 2024 Category: Drugs & Pharmacology Authors: Kosuke Nakashima Yuka Kudo Yasuyuki Matsushima Shin-Ichi Hirashima Tsuyoshi Miura Source Type: research

Late-Stage Derivatization of Oleanolic Acid-Based Anti-HIV-1 Compounds
Chem Pharm Bull (Tokyo). 2024;72(3):330-335. doi: 10.1248/cpb.c23-00891.ABSTRACTA 12-keto-type oleanolic acid derivative (4) has been identified as a potent anti-human immunodeficiency virus type-1 (HIV-1) compound that demonstrates synergistic effects with several types of HIV-1 neutralizing antibodies. In the present study, we used a common key synthetic intermediate to carry out the late-stage derivatization of an anti-HIV compound based on the chemical structure of a 12-keto-type oleanolic acid derivative. To execute this strategy, we designed a diketo-type oleanolic acid derivative (5) for chemoselective transformatio...
Source: Chemical and Pharmaceutical Bulletin - March 24, 2024 Category: Drugs & Pharmacology Authors: Reon Takeuchi Junko Fujimoto Yoshinori Taguchi Ryuji Ide Ryuji Kyan Kohei Sato Nobuyuki Mase Masaru Yokoyama Shigeyoshi Harada Tetsuo Narumi Source Type: research

Synthesis of 2-Substituted Indoles via Migration Reaction of 3-Substituted Indoles with Triflic Acid
This study showcases the 1,2-migration reactions of alkyl and aryl groups on the indole molecule. Trifluoromethanesulfonic acid effectively facilitates the migration of the substituent from C3- to C2-position of the indole structure. The resulting C2-substituted indoles offer a valuable pathway for the synthesis of natural products and medicinal compounds.PMID:38522900 | DOI:10.1248/cpb.c23-00792 (Source: Chemical and Pharmaceutical Bulletin)
Source: Chemical and Pharmaceutical Bulletin - March 24, 2024 Category: Drugs & Pharmacology Authors: Kosuke Nakashima Yuka Kudo Yasuyuki Matsushima Shin-Ichi Hirashima Tsuyoshi Miura Source Type: research

Development of an Auraptene-Loaded Transdermal Formulation Using Non-ionic Sugar Ester Surfactants
Chem Pharm Bull (Tokyo). 2024;72(3):319-323. doi: 10.1248/cpb.c23-00796.ABSTRACTAuraptene (Aur) is a naturally occurring monoterpene coumarin ether that exhibits numerous therapeutic properties. Its high lipophilicity and low skin penetration, however, limit its potential application for local and transdermal delivery. Biocompatible non-ionic sugar esters (SEs) possess beneficial properties for the development of transdermal formulations in delivering pharmaceutically challenging molecules such as graphene and Aur. In the present study, we conducted a series of experiments to demonstrate the effect of several previously un...
Source: Chemical and Pharmaceutical Bulletin - March 20, 2024 Category: Drugs & Pharmacology Authors: Kathrine Anne Flores Akie Okada Florencio Arce Gerard Lee See Shoko Itakura Hiroaki Todo Kenji Sugibayashi Source Type: research

Controlled Release of Lysozyme Using Polyvinyl Alcohol-Based Polymeric Nanofibers Generated by Electrospinning
This study examines the application of electrospun polyvinyl alcohol (PVA) nanofibers for controlled lysozyme (LZM) delivery. By using various PVA grades, such as the degree of polymerization/hydrolysis, this study investigates their influence on nanofiber morphology and drug-release characteristics. LZM-loaded PVA monolithic nanofibers having 50% drug content exhibit efficient entrapment, wherein rapid dissolution is achieved within 30 min. The initial burst of LZM from the nanofiber was reduced as the LZM content was lowered. The initial dissolution is greatly influenced by the choice of PVA grade used; fully hydrolyzed ...
Source: Chemical and Pharmaceutical Bulletin - March 20, 2024 Category: Drugs & Pharmacology Authors: Riho Ogawa Kouji Hara Ayaka Kobayashi Nobuyoshi Yoshimura Yutaka Taniguchi Eriko Yamazoe Takaaki Ito Kohei Tahara Source Type: research

Development of an Auraptene-Loaded Transdermal Formulation Using Non-ionic Sugar Ester Surfactants
Chem Pharm Bull (Tokyo). 2024;72(3):319-323. doi: 10.1248/cpb.c23-00796.ABSTRACTAuraptene (Aur) is a naturally occurring monoterpene coumarin ether that exhibits numerous therapeutic properties. Its high lipophilicity and low skin penetration, however, limit its potential application for local and transdermal delivery. Biocompatible non-ionic sugar esters (SEs) possess beneficial properties for the development of transdermal formulations in delivering pharmaceutically challenging molecules such as graphene and Aur. In the present study, we conducted a series of experiments to demonstrate the effect of several previously un...
Source: Chemical and Pharmaceutical Bulletin - March 20, 2024 Category: Drugs & Pharmacology Authors: Kathrine Anne Flores Akie Okada Florencio Arce Gerard Lee See Shoko Itakura Hiroaki Todo Kenji Sugibayashi Source Type: research

Controlled Release of Lysozyme Using Polyvinyl Alcohol-Based Polymeric Nanofibers Generated by Electrospinning
This study examines the application of electrospun polyvinyl alcohol (PVA) nanofibers for controlled lysozyme (LZM) delivery. By using various PVA grades, such as the degree of polymerization/hydrolysis, this study investigates their influence on nanofiber morphology and drug-release characteristics. LZM-loaded PVA monolithic nanofibers having 50% drug content exhibit efficient entrapment, wherein rapid dissolution is achieved within 30 min. The initial burst of LZM from the nanofiber was reduced as the LZM content was lowered. The initial dissolution is greatly influenced by the choice of PVA grade used; fully hydrolyzed ...
Source: Chemical and Pharmaceutical Bulletin - March 20, 2024 Category: Drugs & Pharmacology Authors: Riho Ogawa Kouji Hara Ayaka Kobayashi Nobuyoshi Yoshimura Yutaka Taniguchi Eriko Yamazoe Takaaki Ito Kohei Tahara Source Type: research

Development of an Auraptene-Loaded Transdermal Formulation Using Non-ionic Sugar Ester Surfactants
Chem Pharm Bull (Tokyo). 2024;72(3):319-323. doi: 10.1248/cpb.c23-00796.ABSTRACTAuraptene (Aur) is a naturally occurring monoterpene coumarin ether that exhibits numerous therapeutic properties. Its high lipophilicity and low skin penetration, however, limit its potential application for local and transdermal delivery. Biocompatible non-ionic sugar esters (SEs) possess beneficial properties for the development of transdermal formulations in delivering pharmaceutically challenging molecules such as graphene and Aur. In the present study, we conducted a series of experiments to demonstrate the effect of several previously un...
Source: Chemical and Pharmaceutical Bulletin - March 20, 2024 Category: Drugs & Pharmacology Authors: Kathrine Anne Flores Akie Okada Florencio Arce Gerard Lee See Shoko Itakura Hiroaki Todo Kenji Sugibayashi Source Type: research

Controlled Release of Lysozyme Using Polyvinyl Alcohol-Based Polymeric Nanofibers Generated by Electrospinning
This study examines the application of electrospun polyvinyl alcohol (PVA) nanofibers for controlled lysozyme (LZM) delivery. By using various PVA grades, such as the degree of polymerization/hydrolysis, this study investigates their influence on nanofiber morphology and drug-release characteristics. LZM-loaded PVA monolithic nanofibers having 50% drug content exhibit efficient entrapment, wherein rapid dissolution is achieved within 30 min. The initial burst of LZM from the nanofiber was reduced as the LZM content was lowered. The initial dissolution is greatly influenced by the choice of PVA grade used; fully hydrolyzed ...
Source: Chemical and Pharmaceutical Bulletin - March 20, 2024 Category: Drugs & Pharmacology Authors: Riho Ogawa Kouji Hara Ayaka Kobayashi Nobuyoshi Yoshimura Yutaka Taniguchi Eriko Yamazoe Takaaki Ito Kohei Tahara Source Type: research

Effect of Two-Photon Excitation to 8-Azacoumarin Derivatives as Photolabile Protecting Groups
Chem Pharm Bull (Tokyo). 2024;72(3):311-312. doi: 10.1248/cpb.c24-00013.ABSTRACTAn improvement of the two-photon excitation was achieved using 8-azacoumarin-type caged compounds, which showed large values of the two-photon uncaging action cross-section (δu >0.1 Goeppert-Mayer (GM)). In particular, the 7-hydroxy-6-iodo-8-azacoumarin (8-aza-Ihc)-caged compound showed an excellent uncaging action cross-section value (δu = 1.28 GM). Therefore, 8-azacoumarin-type photolabile protecting groups (PPGs) can be used as two-photon excitation sources.PMID:38494724 | DOI:10.1248/cpb.c24-00013 (Source: Chemical and Pharmaceutical Bulletin)
Source: Chemical and Pharmaceutical Bulletin - March 18, 2024 Category: Drugs & Pharmacology Authors: Takuya Kobayakawa Hikaru Takano Takahiro Ishii Peter Bolah Kohei Tsuji Nami Ohashi Wataru Nomura Toshiaki Furuta Hirokazu Tamamura Source Type: research

Systematic Studies of Functional Group Tolerance and Chemoselectivity in Carbene-Mediated Intramolecular Cyclopropanation and Intermolecular C-H Functionalization
Chem Pharm Bull (Tokyo). 2024;72(3):313-318. doi: 10.1248/cpb.c24-00022.ABSTRACTGenerating reliable data on functional group compatibility and chemoselectivity is essential for evaluating the practicality of chemical reactions and predicting retrosynthetic routes. In this context, we performed systematic studies using a functional group evaluation kit including 26 kinds of additives to assess the functional group tolerance of carbene-mediated reactions. Our findings revealed that some intermolecular heteroatom-hydrogen insertion reactions proceed faster than intramolecular cyclopropanation reactions. Lewis basic functional...
Source: Chemical and Pharmaceutical Bulletin - March 18, 2024 Category: Drugs & Pharmacology Authors: Haruki Kanda Ayaka Okabe Shingo Harada Tetsuhiro Nemoto Source Type: research

Effect of Two-Photon Excitation to 8-Azacoumarin Derivatives as Photolabile Protecting Groups
Chem Pharm Bull (Tokyo). 2024;72(3):311-312. doi: 10.1248/cpb.c24-00013.ABSTRACTAn improvement of the two-photon excitation was achieved using 8-azacoumarin-type caged compounds, which showed large values of the two-photon uncaging action cross-section (δu >0.1 Goeppert-Mayer (GM)). In particular, the 7-hydroxy-6-iodo-8-azacoumarin (8-aza-Ihc)-caged compound showed an excellent uncaging action cross-section value (δu = 1.28 GM). Therefore, 8-azacoumarin-type photolabile protecting groups (PPGs) can be used as two-photon excitation sources.PMID:38494724 | DOI:10.1248/cpb.c24-00013 (Source: Chemical and Pharmaceutical Bulletin)
Source: Chemical and Pharmaceutical Bulletin - March 18, 2024 Category: Drugs & Pharmacology Authors: Takuya Kobayakawa Hikaru Takano Takahiro Ishii Peter Bolah Kohei Tsuji Nami Ohashi Wataru Nomura Toshiaki Furuta Hirokazu Tamamura Source Type: research