Synthesis of novel 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1, 4]diazepines under microwave irradiation as potential anti-tumor agents

Braulio Insuasty; Angélica García; Jairo Quiroga; Rodrigo Abonia; Manuel Nogueras; Justo Cobo

doi:10.1016/j.ejmech.2010.03.004

Synthesis of novel 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1, 4]diazepines under microwave irradiation as potential anti-tumor agents

Braulio Insuasty
, Angélica García
, Jairo Quiroga
, Rodrigo Abonia
, Manuel Nogueras
, Justo Cobo

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

A new series of 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1,4] diazepines 4a-f and 5a-f were efficiently synthesized in good yields from the reaction of E-2-arylidene-1-tetralones 1 and the respective tri- or tetraaminopyrimidines 2 or 3 under microwave irradiation using DMF as solvent and catalytic amounts of BF₃·OEt₂. Six of the obtained compounds were selected and tested by the National Cancer Institute (NCI-USA) against 60 different tumor cell lines. In particular, compounds 5a, 5c and 5e presented remarkable anti-tumor activity against melanoma cancer in SK-MEL-5 cell line.

Original language	English
Pages (from-to)	2841-2846
Number of pages	6
Journal	European Journal of Medicinal Chemistry
Volume	45
Issue number	7
DOIs	https://doi.org/10.1016/j.ejmech.2010.03.004
State	Published - Jul 2010
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Aminopyrimidines
Antitumoral activity
Arylidene-1-tetralones
Microwave irradiation
Naphtho[1,2-e]pyrimido[4,5-b][1,4] diazepines

Access to Document

10.1016/j.ejmech.2010.03.004

Cite this

@article{51afa7760b594280b341d5b075886217,

title = "Synthesis of novel 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1, 4]diazepines under microwave irradiation as potential anti-tumor agents",

abstract = "A new series of 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1,4] diazepines 4a-f and 5a-f were efficiently synthesized in good yields from the reaction of E-2-arylidene-1-tetralones 1 and the respective tri- or tetraaminopyrimidines 2 or 3 under microwave irradiation using DMF as solvent and catalytic amounts of BF3·OEt2. Six of the obtained compounds were selected and tested by the National Cancer Institute (NCI-USA) against 60 different tumor cell lines. In particular, compounds 5a, 5c and 5e presented remarkable anti-tumor activity against melanoma cancer in SK-MEL-5 cell line.",

keywords = "Aminopyrimidines, Antitumoral activity, Arylidene-1-tetralones, Microwave irradiation, Naphtho[1,2-e]pyrimido[4,5-b][1,4] diazepines",

author = "Braulio Insuasty and Ang{\'e}lica Garc{\'i}a and Jairo Quiroga and Rodrigo Abonia and Manuel Nogueras and Justo Cobo",

note = "Funding Information: The authors wish to credit The Developmental Therapeutics Program (DTP) of the National Cancer Institute of the United States (U.S) for performing the screening of compounds. Authors thank to Colciencias, Universidad del Valle (Colombia) and the Consejer{\'i}a de Innovaci{\'o}n, Ciencia y Empresa (Junta de Andaluc{\'i}a, Spain) , the Universidad de Ja{\'e}n (project reference UJA\_07\_16\_33 ) and Ministerio de Ciencia e Innovaci{\'o}n (project reference SAF2008-04685-C02-02 ) for financial support.",

year = "2010",

month = jul,

doi = "10.1016/j.ejmech.2010.03.004",

language = "English",

volume = "45",

pages = "2841--2846",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier Masson s.r.l.",

number = "7",

}

TY - JOUR

T1 - Synthesis of novel 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1, 4]diazepines under microwave irradiation as potential anti-tumor agents

AU - Insuasty, Braulio

AU - García, Angélica

AU - Quiroga, Jairo

AU - Abonia, Rodrigo

AU - Nogueras, Manuel

AU - Cobo, Justo

N1 - Funding Information: The authors wish to credit The Developmental Therapeutics Program (DTP) of the National Cancer Institute of the United States (U.S) for performing the screening of compounds. Authors thank to Colciencias, Universidad del Valle (Colombia) and the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) , the Universidad de Jaén (project reference UJA_07_16_33 ) and Ministerio de Ciencia e Innovación (project reference SAF2008-04685-C02-02 ) for financial support.

PY - 2010/7

Y1 - 2010/7

N2 - A new series of 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1,4] diazepines 4a-f and 5a-f were efficiently synthesized in good yields from the reaction of E-2-arylidene-1-tetralones 1 and the respective tri- or tetraaminopyrimidines 2 or 3 under microwave irradiation using DMF as solvent and catalytic amounts of BF3·OEt2. Six of the obtained compounds were selected and tested by the National Cancer Institute (NCI-USA) against 60 different tumor cell lines. In particular, compounds 5a, 5c and 5e presented remarkable anti-tumor activity against melanoma cancer in SK-MEL-5 cell line.

AB - A new series of 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1,4] diazepines 4a-f and 5a-f were efficiently synthesized in good yields from the reaction of E-2-arylidene-1-tetralones 1 and the respective tri- or tetraaminopyrimidines 2 or 3 under microwave irradiation using DMF as solvent and catalytic amounts of BF3·OEt2. Six of the obtained compounds were selected and tested by the National Cancer Institute (NCI-USA) against 60 different tumor cell lines. In particular, compounds 5a, 5c and 5e presented remarkable anti-tumor activity against melanoma cancer in SK-MEL-5 cell line.

KW - Aminopyrimidines

KW - Antitumoral activity

KW - Arylidene-1-tetralones

KW - Microwave irradiation

KW - Naphtho[1,2-e]pyrimido[4,5-b][1,4] diazepines

UR - https://www.scopus.com/pages/publications/77954349581

U2 - 10.1016/j.ejmech.2010.03.004

DO - 10.1016/j.ejmech.2010.03.004

M3 - Article

C2 - 20356658

AN - SCOPUS:77954349581

SN - 0223-5234

VL - 45

SP - 2841

EP - 2846

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 7

ER -

Synthesis of novel 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1, 4]diazepines under microwave irradiation as potential anti-tumor agents

Abstract

UN SDGs

Keywords

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