AMINOTHIAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C3H4N2S
Molecular Weight	100.142
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC=CS1

InChI

InChIKey=RAIPHJJURHTUIC-UHFFFAOYSA-N

InChI=1S/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20982388 | books.google.ru/books?id=lfOiJjFQjoEC&pg=PA566&lpg=PA566

Aminothiazole is a heterocyclic amine, commonly used as a starting point for synthesis of many compounds. In 1940s aminothiazole was used for the treatment of thyrotoxicosis. It has a direct action on the thyroid and acts by inhibiting T4 synthesis and accelerating its deiodination. Aminothiazole is an inhibitor of inducible NO synthetase (IC50 18 uM).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nitric oxide synthase, inducible 55 Target ID: CHEMBL3464 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18485715	Inhibitor 8504		18.0 µM [IC50]
Thyroid hormone synthesis 5 Target ID: map04918 Sources: Aminothiazole has a direct action on the thyroid and acts by inhibiting T4 synthesis and accelerating its deiodination.	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Thyrotoxicosis 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20982388	Primary		Approved 8583	ABADOL Approved Use Unknown

PubMed

Title	Date	PubMed
A medicinal chemist's guide to molecular interactions.	2010-07-22	20345171
Synthesis of chiral polyaminothiazoles.	2010-05-10	20218730
Biological characterization of 2-aminothiazole-derived Cdk4/6 selective inhibitor in vitro and in vivo.	2010-04-15	20372067
Discovery of 2-aminothiazoles as potent antiprion compounds.	2010-04	20032192
Cytochrome P450-mediated epoxidation of 2-aminothiazole-based AKT inhibitors: identification of novel GSH adducts and reduction of metabolic activation through structural changes guided by in silico and in vitro screening.	2010-03-15	20095585
Replacement of pyrazol-3-yl amine hinge binder with thiazol-2-yl amine: Discovery of potent and selective JAK2 inhibitors.	2010-03-01	20144546
Metabolic activation of N-thiazol-2-yl benzamide as glucokinase activators: Impacts of glutathione trapping on covalent binding.	2010-03-01	20138764
2-Aminothiadiazole inhibitors of AKT1 as potential cancer therapeutics.	2010-03-01	20137932
The development of a knowledge base for basic active structures: an example case of dopamine agonists.	2010-01-23	20181001
Controlling destiny through chemistry: small-molecule regulators of cell fate.	2010-01-15	20000447
Physical and crystallographic characterisation of the mGlu5 antagonist MTEP and its monohydrochloride.	2010-01	19499574
Novel macrocyclic inhibitors of hepatitis C NS3/4A protease featuring a 2-amino-1,3-thiazole as a P4 carbamate replacement.	2009-11-26	19856919
Nucleophilic capture of the imino-quinone methide type intermediates generated from 2-aminothiazol-5-yl carbinols.	2009-11-19	19827772
Synthesis and antibacterial activity of some new heterocycles incorporating phthalazine.	2009-11	19570595
Potent and cellularly active 4-aminoimidazole inhibitors of cyclin-dependent kinase 5/p25 for the treatment of Alzheimer's disease.	2009-10-01	19700321
Masitinib (AB1010), a potent and selective tyrosine kinase inhibitor targeting KIT.	2009-09-30	19789626
Discovery of leukotriene A4 hydrolase inhibitors using metabolomics biased fragment crystallography.	2009-08-13	19618939
Synthesis and enzymatic evaluation of 2- and 4-aminothiazole-based inhibitors of neuronal nitric oxide synthase.	2009-06-04	19590740
Imidazo[2,1-b]thiazoles and their use as pharmaceuticals: Sanofi-Aventis EP 1 923 062 A1 (equivalent to WO2008058641).	2009-03	19441908
Allosteric modulation of adenosine receptors.	2009-03	18615273
Kinase inhibitors for the treatment of inflammatory and autoimmune disorders.	2009-03	18568424
Design, synthesis, and cytoprotective effect of 2-aminothiazole analogues as potent poly(ADP-ribose) polymerase-1 inhibitors.	2009-02-12	19125579
N(G)-acylated aminothiazolylpropylguanidines as potent and selective histamine H(2) receptor agonists.	2009-02	19072936
Validated quantitative structure-activity relationship analysis of a series of 2-aminothiazole based p56(Lck) inhibitors.	2009-01-05	19046675
Synthesis and Antibacterial Assessment of N-[4-(4-substituted phenyl)-1,3-thiazol-2-yl]-1,3,5-triazin-2-amine.	2009-01	20177467
The potential impact of density dependent fecundity on the use of the faecal egg count reduction test for detecting drug resistance in human hookworms.	2008-10-01	18827883
Initial SAR studies on apamin-displacing 2-aminothiazole blockers of calcium-activated small conductance potassium channels.	2008-10-01	18774291
Preparation of leukotriene B(4) inhibitory active 2- and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives and their growth inhibitory activity on human pancreatic cancer cells.	2008-08-07	18633535
Synthesis and antimicrobial evaluation of some novel 2-aminothiazole derivatives of 4-hydroxy-chromene-2-one.	2008-08	18623301
Synthesis and pharmacological investigation of novel 2-aminothiazole-privileged aporphines.	2008-07-15	18562201
Antioxidant potential of aminothiazole derivative and its protective effect on H(2)O(2)-induced oxidative damage on pBR322 DNA and RBC cellular membrane.	2008-07	18437532
Antioxidant activity of an aminothiazole compound: possible mechanisms.	2008-06-17	18466888
Transition metal cations extraction by ester and ketone derivatives of chromogenic azocalix[4]arenes.	2008-06-15	18023970
SAR and QSAR study on 2-aminothiazole derivatives, modulators of transcriptional repression in Huntington's disease.	2008-05-15	18406155
Discovery of selective aminothiazole aurora kinase inhibitors.	2008-03-20	18307303
New methods for the synthesis of 2-aminothiazolones.	2008-03-07	18237186
Evaluation of a series of bicyclic CXCR2 antagonists.	2008-01-15	18240390
2-Amino-5-thiazolyl motif: a novel scaffold for designing anti-inflammatory agents of diverse structures.	2008-01	17467123
Discovery of potent and specific fructose-1,6-bisphosphatase inhibitors and a series of orally-bioavailable phosphoramidase-sensitive prodrugs for the treatment of type 2 diabetes.	2007-12-19	18041834
Structure-assisted discovery of an aminothiazole derivative as a lead molecule for inhibition of bacterial fatty-acid synthesis.	2007-12	18084068
A rational chemical intervention strategy to circumvent bioactivation liabilities associated with a nonpeptidyl thrombopoietin receptor agonist containing a 2-amino-4-arylthiazole motif.	2007-12	17935300
[Initiation and inhibition of free-radical processes in biochemical peroxidase systems: a review].	2007-11-28	18038676
Observation of O-H...N scalar coupling across a hydrogen bond in nocathiacin I.	2007-06	17431856
Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol.	2007-05-31	17488103
Synthesis of libraries of thiazole, oxazole and imidazole-based cyclic peptides from azole-based amino acids. A new synthetic approach to bistratamides and didmolamides.	2007-05-21	17571182
Copper determination in ethanol fuel by differential pulse anodic stripping voltammetry at a solid paraffin-based carbon paste electrode modified with 2-aminothiazole organofunctionalized silica.	2007-02-15	19071372
Role of an aminothiazole derivative on ethanol-induced toxicity.	2007	20020985
Organosilicon-containing thiazole derivatives as potential lipoxygenase inhibitors and anti-inflammatory agents.	2007	18256725
Evidence for the intermediacy of Wheland-Meisenheimer complexes in SEAr reactions of aminothiazoles with 4,6-dinitrobenzofuroxan.	2007	17868171
Hippocampal neurogenesis, depressive disorders, and antidepressant therapy.	2007	17641737

Patents

Sample Use Guides

In Vivo Use Guide

For the treatment of thyrotoxicosis, aminothiazole was administered orally. The effective dose of the drug is 0.4 g.

Route of Administration: Oral

In Vitro Use Guide

Inducible NO synthetase activity was measured by monitoring the NO concentration generated by the induced iNOS in murine macrophages ANA-1 stimulated by exogenous LPS using a nitric oxide synthase assay kit. The IC50 of aminothiazole in this assay was 18 uM.

Name

Type

Language

2-AMINOTHIAZOLE

Preferred Name

English

AMINOTHIAZOLE

Official Name

English

2-AMINOTHIAZOLE [MI]

Common Name

English

aminothiazole [INN]

Common Name

English

RP-2921

Code

English

RP 2921

Code

English

2-THIAZOLAMINE

Systematic Name

English

NSC-1900

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C885