103740-34-7

Basic information

• Product Name: 4-(3-AMINO-PHENYL)-THIAZOL-2-YLAMINE
• Synonyms: 4-(3-AMINOPHENYL)-1,3-THIAZOL-2-AMINE;4-(3-AMINO-PHENYL)-THIAZOL-2-YLAMINE;4-(3-AMinophenyl)thiazol-2-aMine;[3-(2-aminothiazol-4-yl)phenyl]amine;2-Amino-4-(m-aminophenyl)thiazole;4-(3-aminophenyl)-2-thiazolamine
• CAS NO: 103740-34-7
• Molecular Formula: C₉H₉N₃S
• Molecular Weight: 191.25
• Mol File: 103740-34-7.mol

Chemical Properties

• Boiling Point: 458 °C at 760 mmHg
• Flash Point: 230.8 °C
• Appearance: /
• Density: 1.347 g/cm³
• Vapor Pressure: 1.42E-08mmHg at 25°C
• Refractive Index: 1.715
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(3-AMINO-PHENYL)-THIAZOL-2-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-AMINO-PHENYL)-THIAZOL-2-YLAMINE(103740-34-7)
• EPA Substance Registry System: 4-(3-AMINO-PHENYL)-THIAZOL-2-YLAMINE(103740-34-7)

Safety Data

• Hazardous Substances Data: 103740-34-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(3-AMINO-PHENYL)-THIAZOL-2-YLAMINE is used as a reactant in the synthesis of novel 2-aminothiazole conjugated nitrofuran derivatives. These derivatives exhibit potent antitubercular and antibacterial properties, making them valuable in the development of new drugs to combat tuberculosis and bacterial infections. The compound's reactivity and structural diversity contribute to the design and synthesis of these therapeutic agents, offering potential improvements in treatment options and resistance management.

InChI:InChI=1/C9H9N3S/c10-7-3-1-2-6(4-7)8-5-13-9(11)12-8/h1-5H,10H2,(H2,11,12)

Upstream product

• 72801-61-7 2-(3-acetylphenyl)isoindoline-1,3-dione 
• 17356-08-0 thiourea 
• 1709-44-0 m-aminobenzaldehyde 
• 57493-24-0 4-(3-nitrophenyl)thiazol-2-ylamine 
• 30095-56-8 1-(3-Acetylaminophenyl)-2-bromoethanone 
• 7463-31-2 3-Acetamidoacetophenone 
• 2227-64-7 3'-nitro-2-bromoacetophenone 
• 99-03-6 1-(3-aminophenyl)ethanone 

Downstream Products

• 372096-48-5 [234a] 2-Amino-4-(3-tert-butoxycarbonylaminophenyl)thiazole 
• 97854-82-5 C₁₆H₁₆N₈O₂S₂ 
• 97854-77-8 4-[2-amino-4-(3-amino-phenyl)-thiazol-5-ylazo]-benzenesulfonic acid amide 
• 97854-99-4 4-[2-Amino-4-(3-amino-phenyl)-thiazol-5-ylazo]-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide 

Relevant articles and documents

Pharmacological characterization of a new series of carbamoylguanidines reveals potent agonism at the H2R and D3R

Even today, the role of the histamine H2 receptor (H2R) in the central nervous system (CNS) is widely unknown. In previous research, many dimeric, high-affinity and subtype-selective carbamoylguanidine-type ligands such as UR-NK22 (5, pKi = 8.07) were reported as H2R agonists. However, their applicability to the study of the H2R in the CNS is compromised by their molecular and pharmacokinetic properties, such as high molecular weight and, consequently, a limited bioavailability. To address the need for more drug-like H2R agonists with high affinity, we synthesized a series of monomeric (thio)carbamoylguanidine-type ligands containing various spacers and side-chain moieties. This structural simplification resulted in potent (partial) agonists (guinea pig right atrium, [35S]GTPγS and β-arrestin2 recruitment assays) with human (h) H2R affinities in the one-digit nanomolar range (pKi (139, UR-KAT523): 8.35; pKi (157, UR-MB-69): 8.69). Most of the compounds presented here exhibited an excellent selectivity profile towards the hH2R, e.g. 157 being at least 3800-fold selective within the histamine receptor family. The structural similarities of our monomeric ligands to pramipexole (6), a dopamine receptor agonist, suggested an investigation of the binding behavior at those receptors. The target compounds were (partial) agonists with moderate affinity at the hD2longR and agonists with high affinity at the hD3R (e.g. pKi (139, UR-KAT523): 7.80; pKi (157, UR-MB-69): 8.06). In summary, we developed a series of novel, more drug-like H2R and D3R agonists for the application in recombinant systems in which either the H2R or the D3R is solely expressed. Furthermore, our ligands are promising lead compounds in the development of selective H2R agonists for future in vivo studies or experiments utilizing primary tissue to unravel the role and function of the H2R in the CNS.

Design, synthesis and molecular modelling studies of 1-methyl-3-(4-substituted phenyl-1,3thiazol-2-yl)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1h)-ones as potent anticancer agents

The present study involves the design, synthesis, characterization and molecular docking studies of biologically active quinazolin-4-ones, which were synthesized by condensing 2-amino-4-substituted phenylthiazole with N-methylbenzoxazin-4-one. The N-methylbenzoxazin-4-one and 2-amino-4-substituted phenylthiazole were synthesized from N-methylanthranilic acid and substituted ketones, respectively. The ADME properties determined the synthetic accessibility of quinazolin-4-ones by in silico Swiss ADME. The colorectal anticancer screening was done by using cell HT-29 human colorectal adenocarcinoma based on molecular docking studies on 3GC7-the structure of p38alpha in complex with dihydroquinazolinone. Finally, compounds 5Dh8, 5DF6, 5Db2 and 5Di9 exhibited better activity at a concentration 10 μg/mL when compared to 5-fluorouracil. The ADME properties revealed that all the compounds were within the range and docking studies showed the highest binding with glide score -7.19 and -7.027 Kcal/mol compared to the target protein -10.67 Kcal/mol.

Synthesis and Molecular Docking Studies of Some 1,2-Dimethyl-3(4-substituted phenyl-1,3-thiazol-2-yl)2,3-dihydroquinazolin-4(1H)-ones as Anticancer Agents

Synthesis of 1, 2-dimethyl-3(4-substituted phenyl-1,3-thiazol-2-yl)2,3-dihydro quinazolin-4(1H)-ones (5Aa1-5Ak11) derivatives was effected by refluxing 1,2-dimethylbenzoxazine-4-one with different 4-substituted phenyl-1,3-thiazol-2-amines. Synthesized compounds were characterized through elemental analysis, infrared, proton nuclear magnetic resonance, and Carbon-13 nuclear magnetic resonance. Molecular docking studies were carried out using Schr?dinger Glide (version 2020_1) which was docked into selective P38alpha and Activin A Receptor Type 1 (ACVR1) Activin receptor-like kinase-2 (ALK2) kinase with Protein Data Bank (PDB) code 3GC7, 6GI6. Based on the docking score of synthesized quinazolin-4-one derivatives, co-crystallized ligands interaction was evaluated with 5-fluorouracil (5-FU) as a reference drug. Compounds 5Ae5, 5Aa1, 5Ai9, and 5Ab2 with P38alpha, 5Af6, 5Ae5, 5Ad4, and 5Ab2 with ACVR1 (ALK2) kinase score were -7.265, -7.078, -7.058, and -6.836; -8.929, -8.749, -8.735, and -8.464 Kcal/mol against enzymes responsible for cancer treatment. The results indicated that quinazolin-4-one derivatives had scored better than ligand and 5-FU.

4-Phenylthiazole-2-amine derivative containing urea structure, and preparation method and application thereof

The invention discloses a 4-phenylthiazole-2-amine derivative containing a urea structure, and a preparation method and application thereof. The 4-phenylthiazole-2-amine derivative containing the ureastructure has a structure shown in a formula (I) below:

Identification of novel 2-aminothiazole conjugated nitrofuran as antitubercular and antibacterial agents

The emergence of antibiotic resistant pathogens is an ongoing main problem in the therapy of bacterial infections. In order to develop promising antitubercular and antibacterial lead compounds, we designed and synthesized a new series of derivatives of 2-aminothiazole conjugated nitrofuran with activities against both Mycobacterium tuberculosis and Staphylococcus aureus. Eight compounds 12e, 12k, 12l, 12m, 18a, 18d, 18e, and 18j emerged as promising antitubercular agents. Structure–activity relationships (SARs) were discussed and showed that the derivatives substituted at the position-3 of benzene of 5-nitro-N-(4-phenylthiazol-2-yl)furan-2-carboxamide exhibited superior potency. The most potent compound 18e, substituted with benzamide at this position, displayed minimum inhibitory concentrations (MICs) of 0.27 μg/mL against Mtb H37Ra and 1.36 μg/mL against S. aureus. Furthermore, compound 18e had no obvious cytotoxicity to normal Vero cells (IC50= 50.2 μM). The results suggest that the novel scaffolds of aminothiazole conjugated nitrofuran would be a promising class of potent antitubercular and antimicrobial agents.

ARYL-AMINO SUBSTITUTED PYRROLOPYRIMIDINE MULTI-KINASE INHIBITING COMPOUNDS

Compounds represented by Formula (I): or stereoisomers or pharmaceutically acceptable salts thereof, are inhibitors of least two of the Abl, Aurora-A, Blk, c-Raf, cSRC, Src, PRK2, FGFR3, Flt3, Lck, Mekl, PDK-1, GSK3?, EGFR, p70S6K, BMX, SGK, CaMKII, Tie-2

N-phenylamidines as selective inhibitors of human neuronal nitric oxide synthase: Structure-activity studies and demonstration of in vivo activity

Selective inhibition of the neuronal isoform of nitric oxide synthase (NOS) compared to the endothelial and inducible isoforms may be required for treatment of neurological disorders caused by excessive production of nitric oxide. Recently, we described N-(3-(aminomethyl)benzyl)acetamidine (13) as a slow, tight-binding inhibitor, highly selective for human inducible nitric oxide synthase (iNOS). Removal of a single methylene bridge between the amidine nitrogen and phenyl ring to give N-(3- (aminomethyl)phenyl)acetamidine (14) dramatically altered the selectivity to give a neuronal selective nitric oxide synthase (nNOS) inhibitor. Part of this large shift in selectivity was due to 14 being a rapidly reversible inhibitor of iNOS in contrast to the essentially irreversible inhibition of iNOS observed with 13. Structure-activity studies revealed that a basic amine functionality tethered to an aromatic ring and a sterically compact amidine are key pharmacophores for this class of NOS inhibitors. Maximal nNOS inhibition potency was achieved with N-(3-(aminomethyl)phenyl)-2- furanylamidine (77) (K(i-nNOS) = 0.006 μM; K(i-eNOS) = 0.35 μM; K(i-iNOS) = 0.16 μM). Finally, α-fluoro-N-(3-(aminomethyl)phenyl)acetamidine (74) (K(i- nNOS) = 0.011 μM; K(i-eNOS) = 1.1 μM; K(i-iNOS) = 0.48 μM) had excellent brain penetration and inhibited nNOS in a rat brain slice assay as well as in the rat brain (cerebellum) in vivo. Thus, N-phenylamidines should be useful in validating the role of nNOS in neurological disorders.