Thioanalogues of anti-tumor antibiotics. II. Synthesis and preliminary in vitro cytotoxicity evaluation of tricyclic [1,4]benzothiazepine derivatives

A. Garofalo, G. Balconi, M. Botta, F. Corelli, M. D'Incalci, G. Fabrizi, I. Fiorini, D. Lamba, V. Nacci

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The synthesis of tricyclic [1,4]benzothiazepine derivatives starting from optically active cyclic amino acids and amino alcohols is described. The absolute configurations of the target compounds were assigned by X-ray and 1H-NMR analyses and by molecular modeling studies. The cytotoxic activity of the tricyclic derivatives was tested in vitro by growth inhibition assays using murine L1210 and human lymphoblastic CCRF-CEM leukemias. Compounds 5, 9, and 10 exhibited marked cytotoxic activity.

Original languageEnglish
Pages (from-to)213-220
Number of pages8
JournalEuropean Journal of Medicinal Chemistry
Volume28
Issue number3
DOIs
Publication statusPublished - 1993

Fingerprint

Cyclic Amino Acids
Amino Alcohols
Cytotoxicity
Tumors
Leukemia
X-Rays
Anti-Bacterial Agents
Derivatives
Molecular modeling
Growth
Assays
Neoplasms
Nuclear magnetic resonance
X rays
In Vitro Techniques
Proton Magnetic Resonance Spectroscopy

Keywords

  • 1,4-benzothiazepine
  • cytotoxicity
  • l-thioproline
  • leukemia L1210

ASJC Scopus subject areas

  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Thioanalogues of anti-tumor antibiotics. II. Synthesis and preliminary in vitro cytotoxicity evaluation of tricyclic [1,4]benzothiazepine derivatives. / Garofalo, A.; Balconi, G.; Botta, M.; Corelli, F.; D'Incalci, M.; Fabrizi, G.; Fiorini, I.; Lamba, D.; Nacci, V.

In: European Journal of Medicinal Chemistry, Vol. 28, No. 3, 1993, p. 213-220.

Research output: Contribution to journalArticle

Garofalo, A. ; Balconi, G. ; Botta, M. ; Corelli, F. ; D'Incalci, M. ; Fabrizi, G. ; Fiorini, I. ; Lamba, D. ; Nacci, V. / Thioanalogues of anti-tumor antibiotics. II. Synthesis and preliminary in vitro cytotoxicity evaluation of tricyclic [1,4]benzothiazepine derivatives. In: European Journal of Medicinal Chemistry. 1993 ; Vol. 28, No. 3. pp. 213-220.
@article{f2704c3ac16c4bc6b60f71420dcb3785,
title = "Thioanalogues of anti-tumor antibiotics. II. Synthesis and preliminary in vitro cytotoxicity evaluation of tricyclic [1,4]benzothiazepine derivatives",
abstract = "The synthesis of tricyclic [1,4]benzothiazepine derivatives starting from optically active cyclic amino acids and amino alcohols is described. The absolute configurations of the target compounds were assigned by X-ray and 1H-NMR analyses and by molecular modeling studies. The cytotoxic activity of the tricyclic derivatives was tested in vitro by growth inhibition assays using murine L1210 and human lymphoblastic CCRF-CEM leukemias. Compounds 5, 9, and 10 exhibited marked cytotoxic activity.",
keywords = "1,4-benzothiazepine, cytotoxicity, l-thioproline, leukemia L1210",
author = "A. Garofalo and G. Balconi and M. Botta and F. Corelli and M. D'Incalci and G. Fabrizi and I. Fiorini and D. Lamba and V. Nacci",
year = "1993",
doi = "10.1016/0223-5234(93)90136-3",
language = "English",
volume = "28",
pages = "213--220",
journal = "European Journal of Medicinal Chemistry",
issn = "0223-5234",
publisher = "Elsevier Masson SAS",
number = "3",

}

TY - JOUR

T1 - Thioanalogues of anti-tumor antibiotics. II. Synthesis and preliminary in vitro cytotoxicity evaluation of tricyclic [1,4]benzothiazepine derivatives

AU - Garofalo, A.

AU - Balconi, G.

AU - Botta, M.

AU - Corelli, F.

AU - D'Incalci, M.

AU - Fabrizi, G.

AU - Fiorini, I.

AU - Lamba, D.

AU - Nacci, V.

PY - 1993

Y1 - 1993

N2 - The synthesis of tricyclic [1,4]benzothiazepine derivatives starting from optically active cyclic amino acids and amino alcohols is described. The absolute configurations of the target compounds were assigned by X-ray and 1H-NMR analyses and by molecular modeling studies. The cytotoxic activity of the tricyclic derivatives was tested in vitro by growth inhibition assays using murine L1210 and human lymphoblastic CCRF-CEM leukemias. Compounds 5, 9, and 10 exhibited marked cytotoxic activity.

AB - The synthesis of tricyclic [1,4]benzothiazepine derivatives starting from optically active cyclic amino acids and amino alcohols is described. The absolute configurations of the target compounds were assigned by X-ray and 1H-NMR analyses and by molecular modeling studies. The cytotoxic activity of the tricyclic derivatives was tested in vitro by growth inhibition assays using murine L1210 and human lymphoblastic CCRF-CEM leukemias. Compounds 5, 9, and 10 exhibited marked cytotoxic activity.

KW - 1,4-benzothiazepine

KW - cytotoxicity

KW - l-thioproline

KW - leukemia L1210

UR - http://www.scopus.com/inward/record.url?scp=0027212797&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027212797&partnerID=8YFLogxK

U2 - 10.1016/0223-5234(93)90136-3

DO - 10.1016/0223-5234(93)90136-3

M3 - Article

VL - 28

SP - 213

EP - 220

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

SN - 0223-5234

IS - 3

ER -