BIOMAT Database Logo BIOMAT Database Logo

[Study on substances with antiblastic activity. LIX - Anthramycin and analogs. VIII : synthesis of derivatives of 4H-pyrrolo/1,2-a/[1,5]benzodiazepine]. 1977

F Chimenti, and S Vomero, and R Giuliano, and T M Artico

Preparation of 4H-pyrrolo[1,2-a][1,5]benzodiazepine derivatives related to the antitumoral antibiotic anthramycin, a derivative of 5H-pyrrolo[2,1-c] [1,4]benzodiazepine, is reported. Reaction between 1-(o-acetamidophenyl)-2-dimethylaminomethylpyrrole iodomethylate and potassium cyanide afforded 4,6-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine-5-one, which was then reduced to 5,6-dihydro-4H-pyrrolo[1,2-a][1,5]benzodiazepine by the action of lithium aluminum hydride. Some 6-acylderivatives of the latter compound are also described. The Vilsmeier-Haack reaction on 6-acetyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,5]benzodiazepine furnished the corresponding 1-formyl derivative which was then condensed with ethyl cyanoacetate to give the related compound with the acrylic moiety.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D000876 Anthramycin A broad-spectrum spectrum antineoplastic antibiotic isolated from Streptomyces refuineus var. thermotolerans. It has low toxicity, some activity against Trichomonas and Endamoeba, and inhibits RNA and DNA synthesis. It binds irreversibly to DNA. Anthramycin, (11a alpha)-Isomer,Antramycin
D001570 Benzodiazepinones

Related Publications

F Chimenti, and S Vomero, and R Giuliano, and T M Artico
[Research on substances with antiblastic activity. LXII. Synthesis and antineoplastic activity of pyrrolo-[2,1-b] quinazoline derivatives and of 4H-pyrrolo[2,1-b] [1,3] benzodiazepine derivatives].
April 1978, Il Farmaco; edizione scientifica,
F Chimenti, and S Vomero, and R Giuliano, and T M Artico
[Research on substances with antiblastic activity. LVIII. Synthesis and antineoplastic activity of derivatives of pyrrolo-(1,2-a)quinoxaline].
July 1975, Il Farmaco; edizione scientifica,
F Chimenti, and S Vomero, and R Giuliano, and T M Artico
[Research on substances with antineoplastic activity. IL. Anthramycin and analogue compounds. IV. Synthesis of 6H-pyrrolo-(1,2-a)(1,4)-benzodiazepine].
November 1972, Il Farmaco; edizione scientifica,
F Chimenti, and S Vomero, and R Giuliano, and T M Artico
Research on compounds with antiblastic activity. 43. Synthesis of 9H-pyrrolo-(1,2-a)-indole derivatives.
January 1972, Il Farmaco; edizione scientifica,
F Chimenti, and S Vomero, and R Giuliano, and T M Artico
[Research on substances with antiblastic activity. LXI. Synthesis of 6-amino- and 7-amino-9-keto-9H-pyrrolo[1,2-a]indole derivatives].
April 1978, Il Farmaco; edizione scientifica,
F Chimenti, and S Vomero, and R Giuliano, and T M Artico
[Research on substances with antineoplastic activity. LVI. Anthramycin and analogues. V. Synthesis of derivatives of 7,8-dimethoxy and 7,8-methylendioxy-5H-pyrrolo(2,1-c)(1,4)benzodiazepine].
June 1974, Il Farmaco; edizione scientifica,
F Chimenti, and S Vomero, and R Giuliano, and T M Artico
Pyrrolobenzodiazepine and related systems. I. Synthesis and pharmacological evaluation of new 5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepine derivatives.
December 1990, Farmaco (Societa chimica italiana : 1989),
F Chimenti, and S Vomero, and R Giuliano, and T M Artico
[Research and substances with antineoplastic activity. 48. Anthramycin and analogue compounds. 3. Synthesis and cytostatic activity of derivatives of 10,11-dihydro-5H-pyrrolo(2,1)(1,4)-benzodiazepine-3-carboxyaldehyde].
November 1972, Il Farmaco; edizione scientifica,
F Chimenti, and S Vomero, and R Giuliano, and T M Artico
[Heterocyclic systems. V. Synthesis and CNS activity of derivatives of 6H-pyrrolo (1,2-a) (1,4)-benzodiazepine].
August 1984, Il Farmaco; edizione scientifica,
F Chimenti, and S Vomero, and R Giuliano, and T M Artico
[Heterocyclic systems. IV. Synthesis and CNS activity of derivatives of 4H,6H-pyrrolo[1,2-a][4,1]-benzoxazepine].
November 1983, Il Farmaco; edizione scientifica,
Copied contents to your clipboard!