A simple procedure for preparation of N-thiazol, thiadiazol, pyridyl and sulfanylamidocantharidinimines analogues and evaluation of their cytotoxicities against human HL-60, MCF7, Neuro-2a and A549 carcinoma cell

Ing Jy Tseng, Shiow Yunn Sheu, Ying Tzu Chen, Chu Yun Huang, Ching Tung Lin, Pen Yuan Lin

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8 Citations (Scopus)

Abstract

The lab made an effort to prepare some biological active cantharidinimines by heating the reactant 1 and 2a-g, 5h-i and 7j-r amines to suitable temperature with ethanol to provide 18 N- thiazolyl-, sulfanyl-, aminopyridyl-, bromopyridyl-, alkylpyridyl- and hydroxypyridylcantharidinimines 3a-g, 4a-c, 6h-i and 8j-r in yield of 4-77% (Chart 1). These cantharidinimine derivatives were tested for their capabilities to suppress growth of the human carcinoma cell lines, HL-60, MCF7, Neuro-2a and A549, because the incidence rate is more prominent in Asian countries than western countries. Compounds 3c-d and 6h-i were found to have some antitumor activity in HL-60 but less activity in MCF cell and compounds 8j-l displayed some inhibition effects to A549 cell line, but less effect to Neuro-2a cell line. Compounds 8m-r had no cytotoxic effect against both cell lines. The cytotoxic effects of these cantharidinimine compounds seemed to be better than the cantharidinimide compounds which we had mentioned several years ago.

Original languageEnglish
Pages (from-to)1453-1457
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume60
Issue number11
DOIs
Publication statusPublished - Nov 2012

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Cytotoxicity
Cells
Carcinoma
Cell Line
Heating
Amines
Ethanol
Temperature
Incidence
Growth
Derivatives
A549 Cells

Keywords

  • Cantharidin
  • Cytotoxicity
  • N-azayl-thiadiazolylcantharidinimine
  • Sulfanyl-thiadiazolylcantharidinimine
  • Thiazolyl-thiadiazolylcantharidinimine

ASJC Scopus subject areas

  • Drug Discovery
  • Chemistry(all)

Cite this

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title = "A simple procedure for preparation of N-thiazol, thiadiazol, pyridyl and sulfanylamidocantharidinimines analogues and evaluation of their cytotoxicities against human HL-60, MCF7, Neuro-2a and A549 carcinoma cell",
abstract = "The lab made an effort to prepare some biological active cantharidinimines by heating the reactant 1 and 2a-g, 5h-i and 7j-r amines to suitable temperature with ethanol to provide 18 N- thiazolyl-, sulfanyl-, aminopyridyl-, bromopyridyl-, alkylpyridyl- and hydroxypyridylcantharidinimines 3a-g, 4a-c, 6h-i and 8j-r in yield of 4-77{\%} (Chart 1). These cantharidinimine derivatives were tested for their capabilities to suppress growth of the human carcinoma cell lines, HL-60, MCF7, Neuro-2a and A549, because the incidence rate is more prominent in Asian countries than western countries. Compounds 3c-d and 6h-i were found to have some antitumor activity in HL-60 but less activity in MCF cell and compounds 8j-l displayed some inhibition effects to A549 cell line, but less effect to Neuro-2a cell line. Compounds 8m-r had no cytotoxic effect against both cell lines. The cytotoxic effects of these cantharidinimine compounds seemed to be better than the cantharidinimide compounds which we had mentioned several years ago.",
keywords = "Cantharidin, Cytotoxicity, N-azayl-thiadiazolylcantharidinimine, Sulfanyl-thiadiazolylcantharidinimine, Thiazolyl-thiadiazolylcantharidinimine",
author = "Tseng, {Ing Jy} and Sheu, {Shiow Yunn} and Chen, {Ying Tzu} and Huang, {Chu Yun} and Lin, {Ching Tung} and Lin, {Pen Yuan}",
year = "2012",
month = "11",
doi = "10.1248/cpb.c12-00415",
language = "English",
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pages = "1453--1457",
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issn = "0009-2363",
publisher = "Pharmaceutical Society of Japan",
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TY - JOUR

T1 - A simple procedure for preparation of N-thiazol, thiadiazol, pyridyl and sulfanylamidocantharidinimines analogues and evaluation of their cytotoxicities against human HL-60, MCF7, Neuro-2a and A549 carcinoma cell

AU - Tseng, Ing Jy

AU - Sheu, Shiow Yunn

AU - Chen, Ying Tzu

AU - Huang, Chu Yun

AU - Lin, Ching Tung

AU - Lin, Pen Yuan

PY - 2012/11

Y1 - 2012/11

N2 - The lab made an effort to prepare some biological active cantharidinimines by heating the reactant 1 and 2a-g, 5h-i and 7j-r amines to suitable temperature with ethanol to provide 18 N- thiazolyl-, sulfanyl-, aminopyridyl-, bromopyridyl-, alkylpyridyl- and hydroxypyridylcantharidinimines 3a-g, 4a-c, 6h-i and 8j-r in yield of 4-77% (Chart 1). These cantharidinimine derivatives were tested for their capabilities to suppress growth of the human carcinoma cell lines, HL-60, MCF7, Neuro-2a and A549, because the incidence rate is more prominent in Asian countries than western countries. Compounds 3c-d and 6h-i were found to have some antitumor activity in HL-60 but less activity in MCF cell and compounds 8j-l displayed some inhibition effects to A549 cell line, but less effect to Neuro-2a cell line. Compounds 8m-r had no cytotoxic effect against both cell lines. The cytotoxic effects of these cantharidinimine compounds seemed to be better than the cantharidinimide compounds which we had mentioned several years ago.

AB - The lab made an effort to prepare some biological active cantharidinimines by heating the reactant 1 and 2a-g, 5h-i and 7j-r amines to suitable temperature with ethanol to provide 18 N- thiazolyl-, sulfanyl-, aminopyridyl-, bromopyridyl-, alkylpyridyl- and hydroxypyridylcantharidinimines 3a-g, 4a-c, 6h-i and 8j-r in yield of 4-77% (Chart 1). These cantharidinimine derivatives were tested for their capabilities to suppress growth of the human carcinoma cell lines, HL-60, MCF7, Neuro-2a and A549, because the incidence rate is more prominent in Asian countries than western countries. Compounds 3c-d and 6h-i were found to have some antitumor activity in HL-60 but less activity in MCF cell and compounds 8j-l displayed some inhibition effects to A549 cell line, but less effect to Neuro-2a cell line. Compounds 8m-r had no cytotoxic effect against both cell lines. The cytotoxic effects of these cantharidinimine compounds seemed to be better than the cantharidinimide compounds which we had mentioned several years ago.

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KW - N-azayl-thiadiazolylcantharidinimine

KW - Sulfanyl-thiadiazolylcantharidinimine

KW - Thiazolyl-thiadiazolylcantharidinimine

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