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

被引：7

作者：

Okuda, Kensuke ^{[1
]}

Takechi, Hideyasu ^{[2
]}

Hirota, Takashi ^{[2
]}

Sasaki, Kenji ^{[2
]}

机构：

[1] Gifu Pharmaceut Univ, Lab Med & Pharmaceut Chem, Gifu 5011196, Japan

[2] Okayama Univ, Fac Pharmaceut Sci, Lab Pharmaceut Chem, Kita Ku, Okayama 7008530, Japan

来源：

HETEROCYCLES | 2011年 / 83卷 / 06期

关键词：

Truce-Smiles Rearrangement; Lipoprotein Lipase; Furo[2,3-b]pyridine; Cyclization; Ring Cleavage; TRUCE-SMILES REARRANGEMENT; DERIVATIVES;

D O I：

10.3987/COM-11-12187

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1315 / 1328

页数：14

共 50 条

[1] Polycyclic N-Heterocyclic Compounds, Part 69: Synthesis of 5-amino-1,2-dihydro[1]benzofuro[3,2-d]furo[2,3-b]pyridines and their transformations to related compounds
Okuda, Kensuke
Takano, Jun-ichi
Hirota, Takashi
Sasaki, Kenji
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (02) : 281 - 287
[2] Polycyclic N-Heterocyclic Compounds. Part 64: Synthesis of 5-Amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c]isoquinolines and Related Compounds. Evaluation of Their Bronchodilator Activity and Effects on Lipoprotein Lipase mRNA Expression
Okuda, Kensuke
Deguchi, Hiroshi
Kashino, Setsuo
Hirota, Takashi
Sasaki, Kenji
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (05) : 685 - 689
[3] Synthesis of some new thieno[2,3-b]pyridines, pyrido[3′,2′:4,5]-thieno[3,2-d]pyrimidines and pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]-triazines
Abdel-Rahman, AE
Bakhite, EA
Mohamed, OS
Thabet, EA
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2000, 166 : 149 - 171
[4] Polycyclic N-Heterocyclic Compounds 73: Synthesis and Evaluation of 5-Substituted 1,2-Dihydrofuro[2,3-c]isoquinolines as Inducers of Lipoprotein Lipase mRNA Expression
Okuda, Kensuke
Yoshida, Masahiko
Hirota, Takashi
Sasaki, Kenji
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 : E9 - E11
[5] Polycyclic N-Heterocyclic Compounds. Part 84: Reaction of N-(pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4-yl)amidines or N-(pyrido[2′,3′:4,5]furo[3,2-d]pyrimidin-4-yl)amidines with Hydroxylamine Hydrochloride
Okuda, Kensuke
Ide, Ryota
Uramaru, Naoto
Hirota, Takashi
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (03) : 880 - 887
[6] Polycyclic N-Heterocyclic Compounds. Part 63 Improved Synthesis of 5-Amino-1,2-dihydrofuro[2,3-c]isoquinolines via Truce-Smiles Rearrangement and Subsequent Formation to Furo[2,3-c]isoquinoline
Okuda, Kensuke
Yoshida, Masahiko
Hirota, Takashi
Sasaki, Kenji
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (03) : 363 - 368
[7] Thieno[2,3-b]pyridine-2-carbohydrazide in polyheterocyclic synthesis:: The synthesis of pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine, pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]triazine, and pyrazolyl, oxadiazolylthieno[2,3-b]pyridine derivatives
Elneairy, Mohamed A. A.
Gad-Elkareem, Mohamed A. M.
Abdel-Fattah, Azza M.
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (06) : 1451 - 1466
[8] POLYCYCLIC N-HETEROCYCLIC COMPOUNDS 74: REARRANGEMENT REACTION OF 5-AMINO-1,2-DIHYDROFURO[2,3-c]ISOQUINOLINES WITH α,ω-DIBROMOALKANES AND EVALUATION OF PRODUCT BRONCHODILATOR ACTIVITY
Okuda, Kensuke
Yoshida, Masahiko
Hirota, Takashi
Sasaki, Kenji
[J]. SYNTHETIC COMMUNICATIONS, 2012, 42 (06) : 865 - 871
[9] Synthesis and antibacterial activity of some new ethyl thionicotinates, thieno[2,3-b]pyridines, pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines, and pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]triazines containing sulfonamide moieties
Gad-Elkareem, Mohamed A. M.
El-Adasy, Abu-Bakr A. A. M.
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (02) : 411 - 421
[10] Synthesis and biological activity of some novel thieno[2,3-b]quinoline, quinolino[3',2':4,5] thieno[3,2-d]pyrimidine and pyrido[2',3':4,5] thieno[2,3-b]quinoline derivatives
El-Gaby, MSA
Abdel-Gawad, SM
Ghorab, MM
Heiba, HI
Aly, HM
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (02) : 279 - 297

← 1 2 3 4 5 →