Aminosäureantagonisten. II. β‐[5(6)‐Bis‐(β′‐chloräthyl)‐amino‐benzimidazolyl‐(2)]‐DL‐alanin und Derivate als potentielle Cytostatika

Ozegowski, Werner; Krebs, D.; Wunderwald, M.

doi:10.1002/prac.19630200309

Cited by 15 publications

(1 citation statement)

References 11 publications

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“…Oxytetracyclin was added once weekly to the drinking water (50 mg/1). 3 H20 (ZIMET 3164-hydrochloride) were synthesized in our institute [27]. Cyclophosphamide was purchased from VEB Ankerwerk (Rudolstadt).…”

Section: (A) Animalsmentioning

confidence: 99%

Therapeutic effect, ofβ-[1-phenyl-5-bis(β-chloroethyl)-amino-benzimidazolyl-(2)-Dl-alanin (ZIMET 3164) on immune complex nephritis of NZB hyhrid mice

Güttner

1979

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Beta-[1-Phenyl-5-bis(beta-chloroethyl)-amino-benzimidazolyl-(2)]-DL-alanin (ZIMET 3164), a highly immunosuppressive but moderately cytostatic agent, was found to be able to prevent the progression of spontaneous murine immune complex nephritis in a dose-dependent fashion. For experiments, BCG-stimulated conventional female (NMRI X NZB)F1 mice suffering from rapidly progressive nephritis, BCG-stimulated and unilaterally nephrectomized (NMRI X NZB)F1 females, and (AB/Jena X NZB)F1 females characterized by a prolonged course of the disease were used. The beneficial effect was quantified by fluorescence photometry and histometry, and semiquantitatively detected by estimation of the extent of damage of individual glomerular structures when histometric methods were unsuited. Treatment of young adult animals characterized by slight to moderate glomerular lesions was more effective than of older ones with advanced nephritis. At equi-immunosuppressive dose levels ZIMET 3164 was about twice as effective as the reference substance cyclophosphamide.

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Section: (A) Animalsmentioning

confidence: 99%

Therapeutic effect, ofβ-[1-phenyl-5-bis(β-chloroethyl)-amino-benzimidazolyl-(2)-Dl-alanin (ZIMET 3164) on immune complex nephritis of NZB hyhrid mice

Güttner

1979

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Notiz zur Synthese von 1‐Aryl‐ und 1‐Alkyl‐2, 3‐dimethyl‐chinoxaliniumperchloraten

Schelz

Priester

1975

Helvetica Chimica Acta

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Über die Synthese von 1‐Aryl‐und 1‐Alkyl‐2, 3‐dimethyl‐chinoxalinium‐perchloraten. 2. Mitteilung. Synthese und ¹H‐NMR.‐Spektren von 2,3‐Dimethyl‐1‐phenyl‐6‐X‐chinoxalinium‐perchloraten

Schelz¹

1978

Helvetica Chimica Acta

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The synthesis of the title compounds (5) which have been useful as precursors for a lot of conventional and new-type dyes [2][3][4][5][6][7][8] has yet been limited to examples with X = H [2] [3] [ 111 [15] and with electron-donating [4] [12] or at best slightly electronaccepting [ 11 [6] substituents X and R. We now describe a method suitable even for conipounds 5 with strongly electron-accepting substituents: N-monosubstituted ophenylendiamines 4, were condensed with 2,3-butanedione and perchloric acid in mixed solvents containing an excess of diethyl ether. The productsmostly substituted at position 6 of the quinoxalinium ringare chracterized by 'H-NMR. spectra, elemental analyses and in most cases by isolation of the corresponding bases 6. Correlations of chemical shifts with Hammett's op [18] are given by equations (1)-(5).Salze der 1-substituierten 2,3-Dimethylchinoxaline 5 lassen sich wie andere heterocyclische C-Methyl-quartarsalze als Vorstufen fur die Synthese von Farbstoffen venvenden: Ausgehend von 5 wurde so neben Trimethin-und Hemicyanin-[2] sowie Azamethin-[3,] und Azo-Farbstoffen [4] eine Reihe neuartiger Farbsysteme synthetisiert [5-81. Die Salze 5 werden unter anderem durch Kondensation N-monosubstituierter o-Phenylendiamin e 4 mit 2,3-Butandion in Gegenwart iiberschiissiger Saure HA erhalten (Schema). Kondensationen der Vorstufen 4 mit analogen Dionen sind seit langem bekannt (vgl. z. B. [9] [lo]). Die Synthese eines Salzes 5 nach dieser Methode __-I )

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Aminosäureantagonisten. II. β‐[5(6)‐Bis‐(β′‐chloräthyl)‐amino‐benzimidazolyl‐(2)]‐DL‐alanin und Derivate als potentielle Cytostatika

Abstract: Es wird die Synthese von β‐[Benzimidazolyl‐(2)]‐DL‐alaninen beschrieben, die in 5‐Stellung eine Bis‐(β‐chloräthyl)‐amino‐Gruppe tragen und in 1‐Stellung unsubstituiert oder mit einer Methyl‐, Äthyl‐, Phenyl‐ oder Benzylgruppe substituiert sind.

Cited by 15 publications

References 11 publications

Therapeutic effect, ofβ-[1-phenyl-5-bis(β-chloroethyl)-amino-benzimidazolyl-(2)-Dl-alanin (ZIMET 3164) on immune complex nephritis of NZB hyhrid mice

Therapeutic effect, ofβ-[1-phenyl-5-bis(β-chloroethyl)-amino-benzimidazolyl-(2)-Dl-alanin (ZIMET 3164) on immune complex nephritis of NZB hyhrid mice

Notiz zur Synthese von 1‐Aryl‐ und 1‐Alkyl‐2, 3‐dimethyl‐chinoxaliniumperchloraten

Über die Synthese von 1‐Aryl‐und 1‐Alkyl‐2, 3‐dimethyl‐chinoxalinium‐perchloraten. 2. Mitteilung. Synthese und ¹H‐NMR.‐Spektren von 2,3‐Dimethyl‐1‐phenyl‐6‐X‐chinoxalinium‐perchloraten

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Aminosäureantagonisten. II. β‐[5(6)‐Bis‐(β′‐chloräthyl)‐amino‐benzimidazolyl‐(2)]‐DL‐alanin und Derivate als potentielle Cytostatika

Abstract: Es wird die Synthese von β‐[Benzimidazolyl‐(2)]‐DL‐alaninen beschrieben, die in 5‐Stellung eine Bis‐(β‐chloräthyl)‐amino‐Gruppe tragen und in 1‐Stellung unsubstituiert oder mit einer Methyl‐, Äthyl‐, Phenyl‐ oder Benzylgruppe substituiert sind.

Cited by 15 publications

References 11 publications

Therapeutic effect, ofβ-[1-phenyl-5-bis(β-chloroethyl)-amino-benzimidazolyl-(2)-Dl-alanin (ZIMET 3164) on immune complex nephritis of NZB hyhrid mice

Therapeutic effect, ofβ-[1-phenyl-5-bis(β-chloroethyl)-amino-benzimidazolyl-(2)-Dl-alanin (ZIMET 3164) on immune complex nephritis of NZB hyhrid mice

Notiz zur Synthese von 1‐Aryl‐ und 1‐Alkyl‐2, 3‐dimethyl‐chinoxaliniumperchloraten

Über die Synthese von 1‐Aryl‐und 1‐Alkyl‐2, 3‐dimethyl‐chinoxalinium‐perchloraten. 2. Mitteilung. Synthese und 1H‐NMR.‐Spektren von 2,3‐Dimethyl‐1‐phenyl‐6‐X‐chinoxalinium‐perchloraten

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Über die Synthese von 1‐Aryl‐und 1‐Alkyl‐2, 3‐dimethyl‐chinoxalinium‐perchloraten. 2. Mitteilung. Synthese und ¹H‐NMR.‐Spektren von 2,3‐Dimethyl‐1‐phenyl‐6‐X‐chinoxalinium‐perchloraten