Polycyclic N-heterocyclic compounds. Part 70: Synthesis of 5-amino-1,2-dihydrofuro[2,3-b]pyrido[3',2':4,5]-thieno[3,2-d]pyridines and related compounds. Evaluation of effects on lipoprotein lipase mRNA expression

Kensuke Okuda, Hideyasu Takechi, Takashi Hirota, Kenji Sasaki

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Reaction of 3-(3-cyanopropoxy)thieno[2,3-b]pyridine-2-carbonitriles with potassium tert-butoxide gave 5-amino-1,2-dihydrofuro[2,3-b]pyrido- [3',2':4,5]thieno[3,2-d]pyridines via a Truce-Smiles rearrangement. The 5-amino group was transformed to the chloro derivatives which were allowed to react with various nucleophiles. Effects of the newly synthesized compounds on lipoprotein lipase mRNA expression were also evaluated. The previously unreported parent compound, furo[2,3-b]pyrido[3',2':4,5]thieno[3,2-d]pyridine, was also synthesized.

Original languageEnglish
Pages (from-to)1315-1328
Number of pages14
JournalHeterocycles
Volume83
Issue number6
DOIs
Publication statusPublished - May 26 2011

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Pyridines
Heterocyclic Compounds
Nucleophiles
Lipoprotein Lipase
Derivatives
Messenger RNA
potassium tert-butoxide
pyridine-2-carbonitrile
pyridine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

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title = "Polycyclic N-heterocyclic compounds. Part 70: Synthesis of 5-amino-1,2-dihydrofuro[2,3-b]pyrido[3',2':4,5]-thieno[3,2-d]pyridines and related compounds. Evaluation of effects on lipoprotein lipase mRNA expression",
abstract = "Reaction of 3-(3-cyanopropoxy)thieno[2,3-b]pyridine-2-carbonitriles with potassium tert-butoxide gave 5-amino-1,2-dihydrofuro[2,3-b]pyrido- [3',2':4,5]thieno[3,2-d]pyridines via a Truce-Smiles rearrangement. The 5-amino group was transformed to the chloro derivatives which were allowed to react with various nucleophiles. Effects of the newly synthesized compounds on lipoprotein lipase mRNA expression were also evaluated. The previously unreported parent compound, furo[2,3-b]pyrido[3',2':4,5]thieno[3,2-d]pyridine, was also synthesized.",
author = "Kensuke Okuda and Hideyasu Takechi and Takashi Hirota and Kenji Sasaki",
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TY - JOUR

T1 - Polycyclic N-heterocyclic compounds. Part 70

T2 - Synthesis of 5-amino-1,2-dihydrofuro[2,3-b]pyrido[3',2':4,5]-thieno[3,2-d]pyridines and related compounds. Evaluation of effects on lipoprotein lipase mRNA expression

AU - Okuda, Kensuke

AU - Takechi, Hideyasu

AU - Hirota, Takashi

AU - Sasaki, Kenji

PY - 2011/5/26

Y1 - 2011/5/26

N2 - Reaction of 3-(3-cyanopropoxy)thieno[2,3-b]pyridine-2-carbonitriles with potassium tert-butoxide gave 5-amino-1,2-dihydrofuro[2,3-b]pyrido- [3',2':4,5]thieno[3,2-d]pyridines via a Truce-Smiles rearrangement. The 5-amino group was transformed to the chloro derivatives which were allowed to react with various nucleophiles. Effects of the newly synthesized compounds on lipoprotein lipase mRNA expression were also evaluated. The previously unreported parent compound, furo[2,3-b]pyrido[3',2':4,5]thieno[3,2-d]pyridine, was also synthesized.

AB - Reaction of 3-(3-cyanopropoxy)thieno[2,3-b]pyridine-2-carbonitriles with potassium tert-butoxide gave 5-amino-1,2-dihydrofuro[2,3-b]pyrido- [3',2':4,5]thieno[3,2-d]pyridines via a Truce-Smiles rearrangement. The 5-amino group was transformed to the chloro derivatives which were allowed to react with various nucleophiles. Effects of the newly synthesized compounds on lipoprotein lipase mRNA expression were also evaluated. The previously unreported parent compound, furo[2,3-b]pyrido[3',2':4,5]thieno[3,2-d]pyridine, was also synthesized.

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