Intramolecular reactions of N-acyliminium intermediates

An Overview of Stereoselective Synthesis of α-Aminophosphonic Acids and Derivatives

In this review, recent advances in catalytic asymmetric hydrophosphonylation of aldehydes and imines are discussed. We also summarize several proposed mechanisms for the different possibilities of asymmetric induction and the application of this catalytic methodology to the enantioselective synthesis of α-amino and α-hydroxy phosphonates. A variety of metal-based chiral catalysts as well as several organic catalysts have been exploited as suitable systems for the preparation of enantiomerically pure phosphonates. The recent evolution and future trends of those and other catalytic systems are described.

Catalytic enantioselective hydrophosphonylation of aldehydes and imines

(1986). Peptides and Related Drugs: A Review of Their Absorption, Metabolism, and Excretion. Drug Metabolism Reviews: Vol. 17, No. 3-4, pp. 283-310.

Peptides and Related Drugs: A Review of Their Absorption, Metabolism, and Excretion*

Publisher Summary The chapter discusses the peptide transport by microorganisms. Microbial transport systems involved in uptake of exogenous peptides (and other nutrients) are located in the cytoplasmic membrane. The chapter outlines the mechanisms of peptide transport. A variety of alternative methods to measure peptide transport in microorganisms are discussed. Most of these methods involve some technique for monitoring growth response. Peptides of appropriate amino-acid composition can generally satisfy the nutrient requirements of amino-acid auxotrophs. The chapter explores that in Escherichia coli (E. coli), detailed characterization of the specificities of peptide transport, isolation of transport mutants, and revealed the existence of three peptide permeases. These are the oligopeptide-, dipeptide-, and tripeptide-permeases. The chapter emphasizes on transport and utilization of peptides in fungi such as Saccharomyces cerevisiae and Candida albicans. Peptides are endowed with unique properties in relation to the energetics of substrate translocation. First is their structural variability, which allows neutral, positively- or negatively-charged substrates to be handled by a single system. Second is their oligomeric nature. The chapter also discusses the regulation of peptide permeases.

Peptide Transport by Micro-organisms

Studies on the Synthesis of Chemotherpeutics. Part XI. Synthesis and Antibacterial Activities of Phosphonopeptides

A number of N-acyl and N-(alkoxycarbonyl)-5-fluorouracil derivatives possessing, for example, benzoyl, o-toluyl, acetyl, propionyl, heptanoyl, ethoxycarbonyl, phenoxycarbonyl, and benzyloxycarbonyl groups as N1 and/or N3 substituents were synthesized, and their antitumor activities were evaluated. The synthesis was achieved by a direct and two-step acylation of 5-fluorouracil and by selective N1-deacetylation of N1-acetyl-N3-substituted-5-fluorouracil under appropriate reaction conditions. Several N3-benzoyl- and N3-o-toluyl-5-fluorouracil derivates and showed significant activity against experimental tumor, and N1-acetyl-N3-o-toluyl-5-fluorouracil was found to be most promising among them. Further investigation revealed 12 to retain higher activity toward various tumors, with lower toxicity and good blood level, than either 1 or FT-207, even for oral administration.

Studies on the syntheses of heterocyclic compounds. 845. Studies on the synthesis of chemotherapeutics. 10. Synthesis and antitumor activity of N-acyl- and N-(alkoxycarbonyl)-5-fluorouracil derivatives

Studies on the syntheses of analgesics. Part 50. Synthesis of optically active 2-[4-(1-oxo-2-isoindolinyl)phenyl]propanoic acid. [Studies on the syntheses of heterocyclic compounds. Part 742]†‡

Phenolic cyclisation of 3-(3-aminopropyl)phenol (5) with several carbonyl compounds gave 2,3,4,5-tetrahydro-1H-2-benzazepines (7).

Studies on the syntheses of heterocyclic compounds. Part DLXXVII. Synthesis of 2,3,4,5-tetrahydro-1H-benzazepine derivatives by phenolic cyclisation

Condensations of 3-hydroxybenzylhydrazine with acetone, ethyl methyl ketone, diethyl ketone, cyclohexanone, and 1-methyl-4-piperidone in the presence of acid gave the 1,1-disubstituted 1,2,3,4-tetrahydrophthalazines (2)–(6). On the other hand, the reactions of 3-hydroxybenzoylhydrazine (7) with acetone, cyclohexanone, and benzalde-hyde gave the Schiff's bases (8)–(10).

Studies on the syntheses of heterocyclic compounds. Part DII. Synthesis of 1-substituted 1,2,3,4-tetrahydrophthalazines by a pictet–spengler-type reaction of 3-hydroxybenzylhydrazine with carbonyl compounds

Seiji Haga

Papers

Studies on the Synthesis of Chemotherpeutics. Part XI. Synthesis and Antibacterial Activities of Phosphonopeptides

Studies on the syntheses of heterocyclic compounds. 845. Studies on the synthesis of chemotherapeutics. 10. Synthesis and antitumor activity of N-acyl- and N-(alkoxycarbonyl)-5-fluorouracil derivatives

Studies on the syntheses of analgesics. Part 50. Synthesis of optically active 2-[4-(1-oxo-2-isoindolinyl)phenyl]propanoic acid. [Studies on the syntheses of heterocyclic compounds. Part 742]†‡

Studies on the syntheses of heterocyclic compounds. Part DLXXVII. Synthesis of 2,3,4,5-tetrahydro-1H-benzazepine derivatives by phenolic cyclisation

Studies on the syntheses of heterocyclic compounds. Part DII. Synthesis of 1-substituted 1,2,3,4-tetrahydrophthalazines by a pictet–spengler-type reaction of 3-hydroxybenzylhydrazine with carbonyl compounds