Synthesis and GCP II inhibitory activity of 4[4-(3-bromobenzyl)-5- hydroxyisoxazol-3-yl]benzoic acid heterocyclic analogs

M. Teus; A. Jirgensons; M. Dambrova; R. Mezhapuke

doi:10.1007/s10593-007-0222-7

Synthesis and GCP II inhibitory activity of 4[4-(3-bromobenzyl)-5- hydroxyisoxazol-3-yl]benzoic acid heterocyclic analogs

M. Teus, A. Jirgensons, M. Dambrova, R. Mezhapuke

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

3 Citations (Scopus)

Abstract

A method for the synthesis of analogs of glutamate carboxypeptidase II inhibitor 4-[4-(3-bromobenzyl)-5-hydroxyisoxazol-3-yl]benzoic acid-4-[4-(3-bromobenzyl-5-hydroxypyrazol-3-yl]-benzoic acid and 4-[4-(3-bromobenzyl)-3-hydroxyisoxazol-5-yl]benzoic acid from 4-(2-ethoxycarbonylacetyl)benzoic acid was developed. The GCP II inhibitory activity of all the compounds synthesized was determined. Substitution of the 5-hydroxyisoxazole group by the 5-hydroxypyrazole group led toa complete loss of activity, while replacement with the 3-hydroxyylisoxazole gave the compound with slightly less inhibitoer activity comparing with the initial compound.

Original language	English
Pages (from-to)	1440-1444
Number of pages	5
Journal	Chemistry of Heterocyclic Compounds
Volume	43
Issue number	11
DOIs	https://doi.org/10.1007/s10593-007-0222-7
Publication status	Published - Nov 2007
Externally published	Yes

Keywords*

3-hydroxyisoxazole
5-hydroxyisoxazole
5-hydroxypyrazole
Glutamatecarboxypeptidase II inhibitors

Field of Science*

1.4 Chemical sciences

Publication Type*

1.1. Scientific article indexed in Web of Science and/or Scopus database

Access to Document

10.1007/s10593-007-0222-7

Cite this

@article{7303f98445544fc49f5c181ef6120b16,

title = "Synthesis and GCP II inhibitory activity of 4[4-(3-bromobenzyl)-5- hydroxyisoxazol-3-yl]benzoic acid heterocyclic analogs",

abstract = "A method for the synthesis of analogs of glutamate carboxypeptidase II inhibitor 4-[4-(3-bromobenzyl)-5-hydroxyisoxazol-3-yl]benzoic acid-4-[4-(3-bromobenzyl-5-hydroxypyrazol-3-yl]-benzoic acid and 4-[4-(3-bromobenzyl)-3-hydroxyisoxazol-5-yl]benzoic acid from 4-(2-ethoxycarbonylacetyl)benzoic acid was developed. The GCP II inhibitory activity of all the compounds synthesized was determined. Substitution of the 5-hydroxyisoxazole group by the 5-hydroxypyrazole group led toa complete loss of activity, while replacement with the 3-hydroxyylisoxazole gave the compound with slightly less inhibitoer activity comparing with the initial compound.",

keywords = "3-hydroxyisoxazole, 5-hydroxyisoxazole, 5-hydroxypyrazole, Glutamatecarboxypeptidase II inhibitors",

author = "M. Teus and A. Jirgensons and M. Dambrova and R. Mezhapuke",

note = "Funding Information: This work has been partly supported by the European Social fund within the National Program {"}Support for the Сarrying out Doctoral Studies and Post-doctoral Researches{"}, the project {"}Support for the Development of Doctoral Studies at Riga Technical University {"}, and also with a financial assistance from the Taiho Fund, Latvia.",

year = "2007",

month = nov,

doi = "10.1007/s10593-007-0222-7",

language = "English",

volume = "43",

pages = "1440--1444",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer New York",

number = "11",

}

TY - JOUR

T1 - Synthesis and GCP II inhibitory activity of 4[4-(3-bromobenzyl)-5- hydroxyisoxazol-3-yl]benzoic acid heterocyclic analogs

AU - Teus, M.

AU - Jirgensons, A.

AU - Dambrova, M.

AU - Mezhapuke, R.

N1 - Funding Information: This work has been partly supported by the European Social fund within the National Program "Support for the Сarrying out Doctoral Studies and Post-doctoral Researches", the project "Support for the Development of Doctoral Studies at Riga Technical University ", and also with a financial assistance from the Taiho Fund, Latvia.

PY - 2007/11

Y1 - 2007/11

N2 - A method for the synthesis of analogs of glutamate carboxypeptidase II inhibitor 4-[4-(3-bromobenzyl)-5-hydroxyisoxazol-3-yl]benzoic acid-4-[4-(3-bromobenzyl-5-hydroxypyrazol-3-yl]-benzoic acid and 4-[4-(3-bromobenzyl)-3-hydroxyisoxazol-5-yl]benzoic acid from 4-(2-ethoxycarbonylacetyl)benzoic acid was developed. The GCP II inhibitory activity of all the compounds synthesized was determined. Substitution of the 5-hydroxyisoxazole group by the 5-hydroxypyrazole group led toa complete loss of activity, while replacement with the 3-hydroxyylisoxazole gave the compound with slightly less inhibitoer activity comparing with the initial compound.

AB - A method for the synthesis of analogs of glutamate carboxypeptidase II inhibitor 4-[4-(3-bromobenzyl)-5-hydroxyisoxazol-3-yl]benzoic acid-4-[4-(3-bromobenzyl-5-hydroxypyrazol-3-yl]-benzoic acid and 4-[4-(3-bromobenzyl)-3-hydroxyisoxazol-5-yl]benzoic acid from 4-(2-ethoxycarbonylacetyl)benzoic acid was developed. The GCP II inhibitory activity of all the compounds synthesized was determined. Substitution of the 5-hydroxyisoxazole group by the 5-hydroxypyrazole group led toa complete loss of activity, while replacement with the 3-hydroxyylisoxazole gave the compound with slightly less inhibitoer activity comparing with the initial compound.

KW - 3-hydroxyisoxazole

KW - 5-hydroxyisoxazole

KW - 5-hydroxypyrazole

KW - Glutamatecarboxypeptidase II inhibitors

UR - http://www.scopus.com/inward/record.url?scp=40049112148&partnerID=8YFLogxK

U2 - 10.1007/s10593-007-0222-7

DO - 10.1007/s10593-007-0222-7

M3 - Article

AN - SCOPUS:40049112148

SN - 0009-3122

VL - 43

SP - 1440

EP - 1444

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

IS - 11

ER -

Synthesis and GCP II inhibitory activity of 4[4-(3-bromobenzyl)-5- hydroxyisoxazol-3-yl]benzoic acid heterocyclic analogs

Abstract

Keywords*

Field of Science*

Publication Type*

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