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Unexpected Formation of 11(9 →7)-abeo-Steroid Skeleton in Synthetic Studies toward Batrachotoxin
Chem Pharm Bull (Tokyo). 2024;72(4):360-364. doi: 10.1248/cpb.c24-00126.ABSTRACTBatrachotoxin (1) is a potent cardio- and neurotoxic steroid isolated from certain species of frogs, birds, and beetles. We previously disclosed two synthetic routes to 1. During our synthetic studies toward 1, we explored an alternative strategy for efficiently assembling its 6/6/6/5-membered steroidal skeleton (ABCD-ring). Here we report the application of intermolecular Weix and intramolecular pinacol coupling reactions. While Pd/Ni-promoted Weix coupling linked the AB-ring and D-ring fragments, SmI2-mediated pinacol coupling did not cyclize...
Source: Chemical and Pharmaceutical Bulletin - April 3, 2024 Category: Drugs & Pharmacology Authors: Hiroyuki Mutoh Yuuki Watanabe Daiki Kamakura Koichi Hagiwara Masayuki Inoue Source Type: research

Effects of Saikosaponin-A on Insulin Resistance in Obesity: Computational and Animal Experimental Study
In conclusion, our study suggests that SSA may serve as a therapeutic agent for addressing the metabolic complications associated with obesity. This potential therapeutic effect is attributed to the suppression of inflammatory cytokines and the upregulation of FGF21 and ATG7.PMID:38569867 | DOI:10.1248/cpb.c23-00782 (Source: Chemical and Pharmaceutical Bulletin)
Source: Chemical and Pharmaceutical Bulletin - April 3, 2024 Category: Drugs & Pharmacology Authors: Min-Seong Lee Ji-Won Noh Byung-Cheol Lee Source Type: research

Eperisone Hydrochloride, a Muscle Relaxant, Is a Potent P2X7 Receptor Antagonist
In this study, we discovered that its target protein is the P2X7 receptor. Also, P2X receptor subtype selectivity was high. This finding demonstrates the (Eperisone-P2X7-pain linkage), the validity of P2X7 as a drug target, and the possibility of drug repositioning of Eperisone Hydrochloride.PMID:38556262 | DOI:10.1248/cpb.c24-00032 (Source: Chemical and Pharmaceutical Bulletin)
Source: Chemical and Pharmaceutical Bulletin - March 31, 2024 Category: Drugs & Pharmacology Authors: Makoto Okada Takashi Nose Source Type: research

Development of Methodologies toward the Unified Synthesis of Ellagitannins
Chem Pharm Bull (Tokyo). 2024;72(4):349-359. doi: 10.1248/cpb.c23-00920.ABSTRACTEllagitannins, a class of polyphenols with divergent structures, have attracted considerable attention from synthetic organic chemists. The basic structures in ellagitannins contain esters of D-glucose with galloyl or hexahydroxyldiphenoyl groups, as well as diaryl ether structures. Thus, the synthesis methodologies of such components have been developed by various groups, including our group. This review describes the synthetic methods reported by our group during 2017-2023, aimed at increasing the number of ellagitannins that can be chemicall...
Source: Chemical and Pharmaceutical Bulletin - March 31, 2024 Category: Drugs & Pharmacology Authors: Kazutada Ikeuchi Source Type: research

Magnetic Polystyrene Nanoparticles Prepared by Emulsion Solvent-Evaporation for the Chemiluminescent Immunoassay
In this study, we prepared MPS NPs by emulsion solvent-evaporation without heating. We evaluated the effect of the solvent in the water and organic phases on the magnetic particle content. MPS NPs prepared by 4% (v/v) MeOH aqueous solution and adding stearic acid (SA) (4MeSA-MPS NPs) exhibited the highest magnetic particle content. Furthermore, CLEIA analysis indicates that the C-reactive protein detection limit is 80 pg/mL. Thus, 4MeSA-MPS NPs are promising for clinical diagnoses.PMID:38538315 | DOI:10.1248/cpb.c23-00864 (Source: Chemical and Pharmaceutical Bulletin)
Source: Chemical and Pharmaceutical Bulletin - March 27, 2024 Category: Drugs & Pharmacology Authors: Hiroaki Ichimaru Masashi Kurimoto Shigetoshi Kikuchi 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