1086111-09-2

Usage

Uses

Used in Medicinal Chemistry:
5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole is used as a building block for the development of pharmaceuticals. Its unique structure allows it to be incorporated into the design of new drugs, potentially leading to the creation of novel therapeutic agents.
Used in Materials Science:
In the field of materials science, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole is used in the development of new polymers and other advanced materials. Its dioxaborolane functionality can be exploited to create materials with enhanced properties, such as improved stability or novel reactivity.
Used in Organic Chemistry Research:
5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole is employed as a valuable chemical in the field of organic chemistry research. It serves as a versatile reagent in various organic reactions, enabling the synthesis of complex molecules and the exploration of new reaction pathways. 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole's potential to contribute to scientific advancements makes it an important tool for researchers in the field.

InChI:InChI=1S/C9H14BNO2S/c1-8(2)9(3,4)13-10(12-8)7-5-11-6-14-7/h5-6H,1-4H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 79265-30-8 2-(trimethylsilyl)thiazole 
• 3034-55-7 5-bromo-1,3-thiazole 
• 73183-34-3 bis(pinacol)diborane 
• 863868-37-5 2-(2,6-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 832114-00-8 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole 
• 325143-04-2 4,4,5,5-tetramethyl-2-(2,4,6-trifluorophenyl)-1,3,2-dioxaborolane 
• 1111096-19-5 2-(2,6-difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 1826-13-7 5-phenylthiazole 
• 1175534-96-9 3-(thiazol-5-yl)benzaldehyde 
• 68535-58-0 5-(4-methoxyphenyl)thioazole 
• 252928-83-9 3-(thiazol-5-yl)benzonitrile 
• 1109226-54-1 4-(thiazol-5-yl)benzonitrile 
• 1175534-94-7 2-(thiazol-5-yl)benzonitrile 
• 1175534-98-1 5-(2-nitrophenyl)thiazole 
• 1175534-97-0 ethyl 2-(1,3-thiazol-5-yl)benzoate 
• 198904-40-4 4-(thiazol-5-yl)benzaldehyde 
• 1175534-95-8 2-(thiazol-5-yl)benzaldehyde 
• 332113-79-8 5-(4-Aminophenyl)thiazole 
• 1416000-30-0 2-(thiazol-5-yl)-10-(3-(trifluoromethyl)phenyl) pyrido[3,2-c][1,5]naphthyridin-9(10H)-one 
• 288-47-1 1,3-thiazole 
• 1200129-84-5 5-(3-(4-(piperidin-1-ylmethyl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridin-6-yl)thiazole 

Relevant academic research and scientific papers

Convergent and Practical Synthesis of Fluorescent Triphenylamine Derivatives and Their Localization in Living Cells

In the search for new fluorescent triphenylamine (TP) derivatives, we studied the influence of the position and substitution of diverse heterocyclic substituents. A library of 10 fluorescent triphenylamines bearing either oxazoles or thiazoles and pyridiniums, substituted at different positions has been developed. The approach is based on a convergent C?H activation reaction between pyridine-oxazoles or pyridine-thiazoles and di-iodo triphenylamine. We showed that the nature and substitution pattern of the 5-membered- (oxazole, thiazole) or 6-membered heterocycle (pyridine) has a strong influence on their fluorescence properties and on their localization in living cells as they stain either the nucleus or mitochondria.

Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis

The kinetics and mechanism of the base-catalyzed hydrolysis (ArB(OR)2→ ArB(OH)2) and protodeboronation (ArB(OR)2→ ArH) of a series of boronic esters, encompassing eight different polyols and 10 polyfluoroaryl and heteroaryl moieties, have been investigated by in situ and stopped-flow NMR spectroscopy (19F,1H, and11B), pH-rate dependence, isotope entrainment,2H KIEs, and KS-DFT computations. The study reveals the phenomenological stability of boronic esters under basic aqueous-organic conditions to be highly nuanced. In contrast to common assumption, esterification does not necessarily impart greater stability compared to the corresponding boronic acid. Moreover, hydrolysis of the ester to the boronic acid can be a dominant component of the overall protodeboronation process, augmented by self-, auto-, and oxidative (phenolic) catalysis when the pH is close to the pKaof the boronic acid/ester.

Mitigation of Acetylcholine Esterase Activity in the 1,7-Diazacarbazole Series of Inhibitors of Checkpoint Kinase 1

Checkpoint kinase 1 (ChK1) plays a key role in the DNA damage response, facilitating cell-cycle arrest to provide sufficient time for lesion repair. This leads to the hypothesis that inhibition of ChK1 might enhance the effectiveness of DNA-damaging therapies in the treatment of cancer. Lead compound 1 (GNE-783), the prototype of the 1,7-diazacarbazole class of ChK1 inhibitors, was found to be a highly potent inhibitor of acetylcholine esterase (AChE) and unsuitable for development. A campaign of analogue synthesis established SAR delineating ChK1 and AChE activities and allowing identification of new leads with improved profiles. In silico docking using a model of AChE permitted rationalization of the observed SAR. Compounds 19 (GNE-900) and 30 (GNE-145) were identified as selective, orally bioavailable ChK1 inhibitors offering excellent in vitro potency with significantly reduced AChE activity. In combination with gemcitabine, these compounds demonstrate an in vivo pharmacodynamic effect and are efficacious in a mouse p53 mutant xenograft model.

DIAZACARBAZOLES AND METHODS OF USE

The invention relates to 1,7-diazacarbazole compounds of Formula (I), (I-a) and (I-b) which are useful as kinase inhibitors, more specifically useful as checkpoint kinase 1 (chkl) inhibitors, thus useful as cancer therapeutics. The invention also relates to compositions, more specifically pharmaceutical compositions comprising these compounds and methods of using the same to treat various forms of cancer and hyperproliferative disorders, as well as methods of using the compounds for in vitro, in situ, and in vivo diagnosis or treatment of mammalian cells, or associated pathological conditions.

Synthesis of 5-arylthiazoles. Comparative study between Suzuki cross-coupling reaction and direct arylation

A facile synthetic route to the new thiazol-5-ylboronic acid pinacol ester was described herein. Its reactivity toward Suzuki cross-coupling reaction was studied to provide various 5-arylthiazoles. A comparative study between Suzuki cross-coupling reactio