Synthesis and biological evaluation of new 2-amino-6-(trifluoromethoxy)benzoxazole derivatives, analogues of riluzole

被引：2

作者：

Calabro, Maria Luisa ^{[1
]}

Caputo, Rosanna ^{[1
]}

Ettari, Roberta ^{[2
]}

Puia, Giulia ^{[3
]}

Ravazzini, Federica ^{[3
]}

Zappala, Maria ^{[1
]}

Micale, Nicola ^{[1
]}

机构：

[1] Univ Messina, Dipartimento Sci Farmaco & Prod Salute, I-98168 Messina, Italy

[2] Univ Milan, Dipartimento Sci Farmaceut, I-20133 Milan, Italy

[3] Univ Modena & Reggio Emilia, Dipartimento Sci Biomed, Reggio Emilia, Italy

来源：

MEDICINAL CHEMISTRY RESEARCH | 2013年 / 22卷 / 12期

关键词：

2-Aminobenzoxazole derivatives; Riluzole; Patch-clamp technique; Neuronal primary cultures; Binding assays; AMYOTROPHIC-LATERAL-SCLEROSIS; NEURONS; SODIUM; MECHANISMS; RECEPTORS; GLUTAMATE; RELEASE; TRIAL; NMDA;

D O I：

10.1007/s00044-013-0594-4

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

This manuscript describes the synthesis of a new series of 2-amino-6-(trifluoromethoxy)benzoxazole derivatives (1-5) and a benzothiazine derivative (6) structurally related to riluzole, the only neuroprotective drug currently approved for the treatment of the amyotrophic lateral sclerosis. Preliminary results indicate that the synthesized compounds, in particular benzamide derivatives 3 and 4, are able to antagonize voltage-dependent Na+ channel currents, and therefore they could be exploited as new inhibitors of these channels. Moreover, all compounds possess low binding affinity for GABA and NMDA receptors.

引用

页码：6089 / 6095

页数：7

共 50 条

[31] Synthesis, biological evaluation, and molecular modeling studies of new benzoxazole derivatives as PARP-2 inhibitors targeting breast cancer
Nadeen M. El-Ghobashy
Selwan M. El-Sayed
Ihsan A. Shehata
Mahmoud B. El-Ashmawy
Scientific Reports, 12
[32] Synthesis, biological evaluation, and molecular modeling studies of new benzoxazole derivatives as PARP-2 inhibitors targeting breast cancer
El-Ghobashy, Nadeen M.
El-Sayed, Selwan M.
Shehata, Ihsan A.
El-Ashmawy, Mahmoud B.
SCIENTIFIC REPORTS, 2022, 12 (01)
[33] VERSATILE METHODS FOR THE SYNTHESIS OF 2-AMINO-6-TRIFLUOROMETHOXY-(NITRO)BENZOTHIAZOLES
MIGNANI, S
AUDIAU, F
LEBLEVEC, J
NEMECEK, C
BARREAU, M
JIMONET, P
GUEREMY, C
SYNTHETIC COMMUNICATIONS, 1992, 22 (19) : 2769 - 2780
[34] A NEW ROUTE TO THE SYNTHESIS OF 2-AMINO-6-(METHOXYCARBONYL)AMINO-4-(TETRAHYDROPYRIDYL)PYRIMIDINE 1-OXIDE
MULLER, JC
RAMUZ, H
WAGNER, HP
HELVETICA CHIMICA ACTA, 1983, 66 (03) : 809 - 813
[35] SYNTHESIS OF SOME NEW BENZOXAZOLE, BENZTHIAZOLE AND BENZIMIDAZOLE DERIVATIVES WITH BIOLOGICAL-ACTIVITY
ELSHERIEF, HA
MAHMOUD, AM
ABDELRAHMAN, AE
ELNAGGAR, GM
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1983, 60 (01) : 58 - 60
[36] Synthesis and Biological Evaluation of New Imine- and Amino-Chitosan Derivatives
Abdelwahab, Huda E.
Hassan, Seham Y.
Yacout, Galila A.
Mostafa, Mohamed A.
El Sadek, Mohamed M.
POLYMERS, 2015, 7 (12) : 2690 - 2700
[37] Synthesis and Biological Evaluation of 2-Aminothiazole Analogues of Nα-Protected Amino Acids
Shankaraiah, Lalithamba Haraluru
Govindappa, Nagendra
Sadhanala, Trimurthulu
Siddekha, Aisha
IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION, 2023, 42 (08): : 2494 - 2504
[38] Synthesis and biological evaluation of amino acid derivatives of benzothiophenes
Poojary, B
Belagali, SL
Kumar, KH
Holla, BS
Bhagwat, A
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 10 (04) : 249 - 252
[39] Synthesis and biological evaluation of radioiodinated benzoxazole and benzothiazole derivatives for imaging myelin in multiple sclerosis
Watanabe, Hiroyuki
Ikawa, Miho
Kakae, Masashi
Shirakawa, Hisashi
Kaneko, Shuji
Ono, Masahiro
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2024, 103
[40] DNA interaction, antimicrobial studies of newly synthesized copper (II) complexes with 2-amino-6-(trifluoromethoxy)benzothiazole Schiff base ligands
Rambabu, Aveli
Kumar, Marri Pradeep
Tejaswi, Somapangu
Vamsikrishna, Narendrula
Shivaraj
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 2016, 165 : 147 - 156

← 1 2 3 4 5 →