5304-34-7

Usage

Uses

Used in Chemical Synthesis:
N-PHENACYLTHIAZOLIUM BROMIDE is used as a reactant for the preparation of various thiazolium salts, contributing to the advancement of organic chemistry.
Used in Pharmaceutical Research:
In the Pharmaceutical Industry, N-PHENACYLTHIAZOLIUM BROMIDE is used as a precursor in the synthesis of 2'-deoxyisoguanosine, a compound with potential anti-cancer properties, for the development of novel therapeutic agents.
Used in Biomedical Sciences:
N-PHENACYLTHIAZOLIUM BROMIDE is utilized in fluorescent imaging and photodynamic therapy due to its unique photophysical properties, enhancing diagnostic and treatment options in the biomedical field.

InChI:InChI=1/C11H10NOS.BrH/c13-11(8-12-6-7-14-9-12)10-4-2-1-3-5-10;/h1-7,9H,8H2;1H/q+1;/p-1

Synthetic route

1,3-thiazole (288-47-1) + α-bromoacetophenone (70-11-1) → 2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7)

Conditions	Yield
In methanol for 3h; Reflux; Inert atmosphere;	51%
In benzene for 4h; Heating;	42%

N-p-tolylphenylmaleimide (1631-28-3) + 2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → (5S,5aS,8aS,8bR)-5-Benzoyl-7-p-tolyl-5,5a,8a,8b-tetrahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]thiazole-6,8-dione

Conditions	Yield
With triethylamine In dichloromethane for 0.166667h; Ambient temperature;	97%

3-(2,3-diphenyl-2-cyclopropenylidene)-2,4-pentanedione (15104-20-8) + 2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → C31H25NO3S (82735-59-9)

Conditions	Yield
With triethylamine In tetrahydrofuran 1.) rt, 2 h; 2) reflux, 2 h;	93%

2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → 3-(2-Hydroxy-2-phenyl-ethyl)-thiazol-3-ium; bromide

Conditions	Yield
With sodium tetrahydroborate In water Ambient temperature;	76%

2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) + dimethylfumarate (624-49-7) → (5R,6R,7S,7aS)-5-Benzoyl-5,6,7,7a-tetrahydro-pyrrolo[2,1-b]thiazole-6,7-dicarboxylic acid dimethyl ester + (5R,6S,7R,7aS)-5-Benzoyl-5,6,7,7a-tetrahydro-pyrrolo[2,1-b]thiazole-6,7-dicarboxylic acid dimethyl ester

Conditions	Yield
With triethylamine In chloroform for 0.166667h; Ambient temperature; Title compound not separated from byproducts;	A 50% B 50%

(E)-1-(4-methylphenyl)-3-phenyl-2-propen-1-one (14802-30-3) + 2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → ((5R,6R,7R,7aR)-5-Benzoyl-6-phenyl-5,6,7,7a-tetrahydro-pyrrolo[2,1-b]thiazol-7-yl)-p-tolyl-methanone

Conditions	Yield
With triethylamine CHCl3, r.t., 14 h; Yield given. Multistep reaction;

2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) + 2-oxopropanal (78-98-8) → 5-benzoyl-6,7-dihydroxy-7-methyl-6,7-dihydro-5H-pyrrolo[2,1-b]thiazol-4-ylium

Conditions	Yield
With phosphate buffer In water at 37℃; for 24h; pH=7.4;

2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → 3-((E)-Styryl)-thiazol-3-ium; bromide

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / NaBH4 / H2O / Ambient temperature 2: 73 percent / benzoyl chloride / 190 - 200 °C View Scheme

2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → Thiazolo[2,3-a]isoquinolin-4-ylium; bromide

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent / NaBH4 / H2O / Ambient temperature 2: 73 percent / benzoyl chloride / 190 - 200 °C 3: I2 / methanol / Ambient temperature; Irradiation View Scheme

Upstream product

• 288-47-1 1,3-thiazole 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 82735-59-9 C₃₁H₂₅NO₃S 

Relevant academic research and scientific papers

Synthesis and evaluation of naphthoic acid derivatives as fluorescent probes to screen advanced glycation end-products breakers

Advanced glycation end-products, namely AGEs, are involved in the pathogenesis of numerous diseases. If AGEs inhibitors are well-known, only few products are described as compounds able to destroy those deleterious products. In this work, we describe naphthoic acid derivatives, particularly 1-(naphthalen-1-yl)propane-1,2-dione 9, allowing the simple and rapid detection of AGEs breakers using a 96-well microplate fluorescence assay. Since the inaugurate publication about AGEs breakers whose activity was demonstrated using HPLC analysis, this work proposes the first assay suitable for automated and high throughput screening of AGEs breakers.

Methods of Treating or Preventing Cardiac Disease Associated With a High Fat Diet

The present invention relates to a method of treating or preventing cardiac disorders, myocardial inflammation or myocardial oxidative stress associated with a high fat diet or in a patient subjected to a high fat diet using the thiazolium compounds and compositions of the invention. The present invention also relates to a method of ameliorating weight gain, myocardial AGE accumulation associated, mitochondrial superoxide production, RAGE expression or PPARα expression with a high fat diet or in a patient subjected to a high fat diet using the thiazolium compounds and compositions of the invention.

Method and composition for rejuvenating hair, nails, tissues, cells and organs by ex-vivo or immersive treatment

A method and composition for the treatment of hair, nail, ex-vivo organ, ex-vivo cell or ex-vivo tissue to improve the biomechanical and diffusional characteristics comprising an effective amount of a compound selected from the group consisting of compounds of the formula

Method for treating fibrotic diseases or other indications IC

Provided, among other things, is a method of treating or ameliorating or preventing an indication of the invention in an animal, including a human comprising administering an effective amount of a compound of the formula I:

Preventing and reversing the formation of advanced glycosylation endproducts

The present invention relates to compositions and methods for inhibiting and reversing nonenzymatic cross-linking (protein aging). Accordingly, compositions are disclosed which comprise an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins, and which additionally reverse pre-formed crosslinks in the advanced glycosylation endproducts by cleaving alpha-dicarbonyl-based protein crosslinks present in the advanced glycosylation endproducts. Certain agents useful are thiazolium salts. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated. A novel immunoassay for detection of the reversal of the nonenzymatic crosslinking is also disclosed.

Preventing and reversing advanced glycosylation endproducts

The present invention relates to compositions and methods for inhibiting and reversing nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises a thiazolium compound capable of inhibiting, and to some extent reversing, the formation of advanced glycosylation endproducts of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated. A novel immunoassay for detection of the reversal of the nonenzymatic crosslinking is also disclosed.

Synthesis and Nitration of Some Thieno-fused Analogues of the Benzo[a]quinolizinium Cation

Three thieno-fused analogues of benzo[a]quinolizinium (1), thieno[3,2-a]- and thieno[2,3-a]quinolizinimn 4 and 5 and thiazolo[2,3-a]isoquinolinium (6), were synthesized by photocyclization of 1-(2-thienylvinyl)pyridinium salts 9a and 9b and 3-styrylthiazolium salt 9c, respectively. The nitration of the compounds 4, 5, and 6 occurred predominantly at positions 2, 3, and 7, respectively, while the nitro group was introduced into the 8- and 10-positions of 1 in the ratio of 68:32. The nmr and uv spectral properties and reduction potentials of 4-6 were also compared with those of the parent compound 1.