1003-32-3

Usage

Uses

Used in Pharmaceutical Industry:
Thiazole-5-carboxaldehyde is used as a key intermediate in the synthesis of imidazoles, which possess cardiomyocyte proliferation activity. This application is particularly relevant for the development of heart disease treatments, as these imidazoles can potentially promote the growth and repair of heart muscle cells, contributing to the regeneration and overall health of the heart.

Synthesis Reference(s)

Synthetic Communications, 25, p. 4081, 1995 DOI: 10.1080/00397919508011485Synthesis, p. 998, 1987 DOI: 10.1055/s-1987-28146

Purification Methods

Dry the aldehyde over Na2SO4 and fractionate it in a vacuum. The 2,4-dinitrophenylhydrazone forms red crystals from MeOH with m 238-240o, and the semicarbazone has m 210-212o (from MeOH). [Erne et al. Helv Chim Acta 34 148 1951, Beilstein 27 III/IV 2615.]

InChI:InChI=1/C4H3NOS/c6-2-4-1-5-3-7-4/h1-3H

Upstream product

• 92972-48-0 2,4-dichlorothiazole-5-carboxaldehyde 
• 38585-74-9 thiazol-5-yl-methanol 
• 4394-85-8 4-morpholinecarboxaldehyde 
• 116045-56-8 2-Trimethylsilanyl-thiazole-5-carbaldehyde 
• 463-04-7 n-Amyl nitrite 
• 2065-75-0 2-Bromo-malonaldehyde 
• 139669-95-7 2,4-dibromo-1,3-thiazole-5-carbaldehyde 

Downstream Products

• 1057001-95-2 2-phenyl-4-thiazol-5-ylmethylen-4H-oxazol-5-one 
• 143817-22-5 [4-(3,3-Diphenyl-propionyl)-piperazin-1-yl]-thiazol-5-yl-acetonitrile 
• 116045-57-9 1,3-thiazole-5-carbaldehyde oxime 
• 38585-74-9 thiazol-5-yl-methanol 
• 927437-51-2 Benzyl-[1-thiazol-5-yl-meth-(E)-ylidene]-amine 
• 216087-27-3 5-[1-(R*,S*)-hydroxy-3-cyclohexylpropyl]thiazole 
• 238749-53-6 ethyl 4H-pyrrolo[2,3-d]thiazole-5-carboxylate 
• 857295-39-7 2-methoxy-4-[(thiazol-5-ylmethyl)-amino]-benzoic acid methyl ester 
• 1257049-79-8 4-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-{[4-({3-[cyclopropyl(1,3-thiazol-5-ylmethyl)amino]propyl}amino)-3-nitrophenyl]sulfonyl}-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide 
• 1388020-62-9 5-((2,6-diphenyl-4H-pyran-4-yliden)methyl)thiazole 

Relevant academic research and scientific papers

A New Convenient Preparation of 2-, 4-, and 5-Thiazolecarboxaldehydes and Their Conversion into the Corresponding Carbonitrile N-Oxides: Synthesis of 3-Thiazolylisoxazoles and 3-Thiazolylisoxazolines

The title aldehydes are prepared in high yields by quenching 2-lithiothiazole, 4-lithio-, and 5-lithio-2-trimethylsilylthiazole with N-formylmorpholine followed by protodesilylation in the latter two cases.The aldehydes are transformed through their oxime

Catalytic hydrogenation of halothiazoles

The hydrogenation of halothiazoles is described. The best results were obtained utilizing 10% palladium on carbon as catalyst at four atmospheres of pressure with the bromide derivatives.

Preclinical Optimization of gp120 Entry Antagonists as anti-HIV-1 Agents with Improved Cytotoxicity and ADME Properties through Rational Design, Synthesis, and Antiviral Evaluation

We previously reported a milestone in the optimization of NBD-11021, an HIV-1 gp120 antagonist, by developing a new and novel analogue, NBD-14189 (Ref1), which showed antiviral activity against HIV-1HXB2, with a half maximal inhibitory concentr

SUBSTITUTED HETEROCYCLICS WITH THERAPEUTIC ACTIVITY IN HIV

Substituted heterocyclic substituted pyrrole carboxamide compounds such as those represented by Formula I or Formula II are provided herein. Such compounds, or pharmaceutically acceptable salts thereof, can be used in the treatment of HIV infection and re

Chemical Compounds

This invention relates to non-steroidal compounds that are modulators of androgen, glucocorticoid, mineralocorticoid, and progesterone receptors, and also to the methods for the making and use of such compounds.

6-O-substituted erythromycin derivatives having improved gastrointestinal tolerance

Compounds having formula (I) are useful for treating bacterial infections while avoiding the concomitant liability of gastrointestinal intolerance. Compositions containing the compounds and methods of treatment using the compounds are also disclosed.

Inhibitors of protein isoprenyl transferases

Compounds having the formula or a pharmaceutically acceptable salt thereof wherein R1is (a) hydrogen, (b) loweralkyl, (c) alkenyl, (d) alkoxy, (e) thioalkoxy, (f) halo, (g) haloalkyl, (h) aryl-L2—, and (i) heterocyclic-L2—; R2is selected from (a) (b) —C(O)NH—CH(R14)—C(O)OR15, (d) —C(O)NH—CH(R14)—C(O)NHSO2R16, (e) —C(O)NH—CH(R14)-tetrazolyl, (f) —C(O)NH-heterocyclic, and (g) —C(O)NH—CH(R14)—C(O)NR17R18; R3is substituted or unsubstituted heterocyclic or aryl, substituted or unsubstituted cycloalkyl or cycloalkenyl, and —P(W)RR3RR3′; R4is hydrogen, lower alkyl, haloalkyl, halogen, aryl, arylakyl, heterocyclic, or (heterocyclic)alkyl; L1is absent or is selected from (a) —L4—N(R5)—L5—, (b) —L4—O—L5—, (c) —L4—S(O)n—L5— (d) —L4—L6—C(W)—N(R5)—L5—, (e) —L4—L6—S(O)m—N(R5)—L5—, (f) —L4—N(R5)—C(W)—L7—L5—, (g) —L4—N(R5)—S(O)p—L7—L5—, (h) optionally substituted alkylene, (i) optionally substituted alkenylene, (j) optionally substituted alkynylene (k) a covalent bond, (l) and (m) are inhibitors of protein isoprenyl transferases. Also disclosed are protein isoprenyl transferase inhibiting compositions and a method of inhibiting protein isoprenyl transferases.

Thiazole derivatives

The invention provides thiazole derivatives of the general formula I: STR1 or acid-addition salts or metal salt complexes thereof, in which R represents an optionally substituted phenyl group; A represents a group STR2 R1 represents a hydrogen