Synthesis, unambiguous chemical characterization, and reactivity of 2,3,4,5-tetrahydro-1,5-benzoxazepines-3-ol

被引：10

作者：

Eugenia Garcia-Rubino, M. ^{[1
]}

Nunez, Maria C. ^{[1
]}

Gallo, Miguel A. ^{[1
]}

Campos, Joaquin M. ^{[1
]}

机构：

[1] Fac Farm, Dept Quim Farmaceut & Organ, Granada 18071, Spain

来源：

RSC ADVANCES | 2012年 / 2卷 / 33期

关键词：

ANTICANCER ACTIVITY; DERIVATIVES; DESIGN;

D O I：

10.1039/c2ra21706f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The previous structures of several 3,4-dihydro-2H-3-hydroxymethyl-1,4-benzoxazines were erroneous (Bioorg. Med. Chem. Lett. 2006, 16, 2862; Synlett 2009, 3283 and Chinese Patent 2006-10043245). The results presented here are both detailed NMR experiments and synthetic aspects on this subject. We redress some points for the preparation of intermediates of the target molecules.

引用

页码：12631 / 12635

页数：5

共 22 条

[1] Synthesis of some new 3,4-dihydro-2H-1,3-benzoxazines under microwave irradiation in solvent-free conditions and their biological activity [J].

Akhter, Mymoona ;

Habibullah, Shaikh ;

Hasan, Syed Misbahul ;

Alam, Mohammad Mumtaz ;

Akhter, N. ;

Shaquiquzzaman, Mohammad .

MEDICINAL CHEMISTRY RESEARCH, 2011, 20 (08) :1147-1153

[2] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[3] Synthesis and anticancer activity of (RS)-9-(2,3-dihydro-1,4-benzoxaheteroin-2-ylmethyl)-9H-purines [J].

Conejo-Garcia, Ana ;

Eugenia Garcia-Rubino, M. ;

Marchal, Juan A. ;

Carmen Nunez, M. ;

Ramirez, Alberto ;

Cimino, Sandro ;

Angel Garcia, M. ;

Aranega, Antonia ;

Gallo, Miguel A. ;

Campos, Joaquin M. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) :3795-3801

[4] Syntheses of 2,3-Dihydro-1,4-Benzodioxins and Bioisosteres as Structural Motifs for Biologically Active Compounds [J].

Cruz-Lopez, Olga ;

Nunez, Maria C. ;

Conejo-Garcia, Ana ;

Kimatrai, Maria ;

Campos, Joaquin M. .

CURRENT ORGANIC CHEMISTRY, 2011, 15 (06) :869-887

[5] Anticancer activity of (1,2,3,5-tetrahydro-4,1-benzoxazepine-3-yl)-pyrimidines and -purines against the MCF-7 cell line:: Preliminary cDNA microarray studies [J].

Diaz-Gavilan, Monica ;

Gomez-Vidal, Jose A. ;

Rodriguez-Serrano, Fernando ;

Marchal, Juan A. ;

Caba, Octavio ;

Aranega, Antonia ;

Gallo, Miguel A. ;

Espinosa, Antonio ;

Campos, Joaquin M. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (04) :1457-1460

[6] Synthesis and anticancer activity of (R,S)-9-(2,3-dihydro-1,4-benzoxathiin-3-ylmethyl)-9H-purines [J].

Diaz-Gavilan, Monica ;

Conejo-Garcia, Ana ;

Cruz-Lopez, Olga ;

Nunez, Maria C. ;

Choquesillo-Lazarte, Duane ;

Gonzalez-Perez, Josefa M. ;

Rodriguez-Serrano, Fernando ;

Marchal, Juan A. ;

Aranega, Antonia ;

Gallo, Miguel A. ;

Espinosa, Antonio ;

Campos, Joaquin M. .

CHEMMEDCHEM, 2008, 3 (01) :127-135

[7] (2,3-Dihydro-1,4-benzodioxin-2-yl)methanol [J].

Gavilan, Monica Diaz ;

Choquesillo-Lazarte, Duane ;

Campos, Joaquin M. .

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 :O2940-U2738

[8]

Guillaumet G., 1996, COMPREHENSIVE HETERO, V6, P447

[9]

Hamamura K., 2004, [No title captured], Patent No. [WO 2004-JP12322, 12322]

[10] Design and synthesis of new prostaglandin D2 receptor antagonists [J].

Iwahashi, Maki ;

Takahashi, Eiji ;

Tanaka, Motoyuki ;

Matsunaga, Yoko ;

Okada, Yutaka ;

Matsumoto, Ryoji ;

Nambu, Fumio ;

Nakai, Hisao ;

Toda, Masaaki .

BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (18) :5361-5371

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