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Synthesis of a new series of biologically interesting 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives.

Brzozowski Z, Żołnowska B, Sławiński J - Monatsh. Chem. (2013)

Bottom Line: A series of 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives have been synthesized from isatoic anhydride and 3-(R(2)-amino)-1,4,2-benzodithiazine 1,1-dioxides.Some synthetic limitations are discussed on the basis of quantum chemical calculations performed by use of the Hartree-Fock method.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdańsk, Gen. J. Hallera Str. 107, 80416 Gdańsk, Poland.

ABSTRACT

Abstract: A series of 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives have been synthesized from isatoic anhydride and 3-(R(2)-amino)-1,4,2-benzodithiazine 1,1-dioxides. Some synthetic limitations are discussed on the basis of quantum chemical calculations performed by use of the Hartree-Fock method.

No MeSH data available.


General structures of 6-chloro-1,4,2-benzodithiazine 1,1-dioxide derivatives I, II, III, and VI, 2-mercaptobenzenesulfonamides IV, and spiro[4H-benzo[d][1,3,7]oxadiazocine-4,3′(2′H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives V and VII
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Fig1: General structures of 6-chloro-1,4,2-benzodithiazine 1,1-dioxide derivatives I, II, III, and VI, 2-mercaptobenzenesulfonamides IV, and spiro[4H-benzo[d][1,3,7]oxadiazocine-4,3′(2′H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives V and VII

Mentions: Compounds containing the 1,1-dioxo-1,4,2-benzodithiazine ring system were synthesized in our laboratories in 1984 and have attracted much attention for several years because of their wide range of biological activity. It has been demonstrated that many 6-chloro-1,4,2-benzodithiazine derivatives (Fig. 1, type I) have low acute toxicity to mice and rats and, depending on their structure, act as potential radio-protective [1, 2], diuretic [1–5], or cholagogue [5] agents. It has also been shown that some 6-chloro-1,1-dioxo-1,4,2-benzodithiazines have remarkable antitumor activity (Fig. 1, types I [6–8] and II [9, 10]) or anti-HIV activity (Fig. 1, types I [11, 12], II [9], and III [13]).Fig. 1


Synthesis of a new series of biologically interesting 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives.

Brzozowski Z, Żołnowska B, Sławiński J - Monatsh. Chem. (2013)

General structures of 6-chloro-1,4,2-benzodithiazine 1,1-dioxide derivatives I, II, III, and VI, 2-mercaptobenzenesulfonamides IV, and spiro[4H-benzo[d][1,3,7]oxadiazocine-4,3′(2′H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives V and VII
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4495064&req=5

Fig1: General structures of 6-chloro-1,4,2-benzodithiazine 1,1-dioxide derivatives I, II, III, and VI, 2-mercaptobenzenesulfonamides IV, and spiro[4H-benzo[d][1,3,7]oxadiazocine-4,3′(2′H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives V and VII
Mentions: Compounds containing the 1,1-dioxo-1,4,2-benzodithiazine ring system were synthesized in our laboratories in 1984 and have attracted much attention for several years because of their wide range of biological activity. It has been demonstrated that many 6-chloro-1,4,2-benzodithiazine derivatives (Fig. 1, type I) have low acute toxicity to mice and rats and, depending on their structure, act as potential radio-protective [1, 2], diuretic [1–5], or cholagogue [5] agents. It has also been shown that some 6-chloro-1,1-dioxo-1,4,2-benzodithiazines have remarkable antitumor activity (Fig. 1, types I [6–8] and II [9, 10]) or anti-HIV activity (Fig. 1, types I [11, 12], II [9], and III [13]).Fig. 1

Bottom Line: A series of 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives have been synthesized from isatoic anhydride and 3-(R(2)-amino)-1,4,2-benzodithiazine 1,1-dioxides.Some synthetic limitations are discussed on the basis of quantum chemical calculations performed by use of the Hartree-Fock method.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdańsk, Gen. J. Hallera Str. 107, 80416 Gdańsk, Poland.

ABSTRACT

Abstract: A series of 6'-chloro-1',1'-dioxospiro[4H-benzo[d][1,3,7]oxadiazocine-4,3'(2'H)-[1,4,2]benzodithiazine]-2,6(1H,5H)dione derivatives have been synthesized from isatoic anhydride and 3-(R(2)-amino)-1,4,2-benzodithiazine 1,1-dioxides. Some synthetic limitations are discussed on the basis of quantum chemical calculations performed by use of the Hartree-Fock method.

No MeSH data available.