29886-65-5

Usage

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 4407, 1986 DOI: 10.1016/S0040-4039(00)84964-3

Upstream product

• 42545-43-7 2-(4-methoxyphenyl)thiophene 
• 696-62-8 para-iodoanisole 
• 6165-68-0 thiophene boronic acid 
• 106-41-2 4-bromo-phenol 
• 540-38-5 p-Iodophenol 
• 1003-09-4 2-bromothiophene 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 1168076-29-6 5-(4-methoxyphenyl)thiophene-2-sulphonic acid tert-butylamide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1027937-46-7 4,4-Dimethoxy-1-thiophen-2-yl-cyclohexa-2,5-dienol 
• 33527-94-5 4-acetoxyiodobenzene 
• 54663-78-4 tributyl(thien-2-yl)stannane 

Downstream Products

• 185993-18-4 3-(4-n0decylphenyl)thiophene 
• 185993-19-5 5-(4-n-decyloxyphenyl)thiophene-2-carboxylic acid 
• 209592-52-9 2-(4-ethoxyphenyl)thiophene 
• 1307226-04-5 propargyl 4-(2-thienyl)phenyl ether 
• 1454583-61-9 C₂₈H₃₆O₃S₂ 
• 1454583-65-3 C₃₂H₄₄O₃S₂ 
• 1454583-68-6 C₃₆H₅₂O₃S₂ 

Relevant academic research and scientific papers

Photo-Fries reaction in acetoxyphenyl thiophenes

Two new acetoxyphenyl thiophenes with different conjugation length and undergoing the photo-Fries reaction upon exposure to UV light are presented. These molecules have been characterized in solution by means of different spectroscopic techniques in order to study the evolution and selectivity of the photo-induced reaction. During such a reaction, isosbestic points appear in the UV–vis spectra, indicating a good selectivity of the reaction for both the derivatives. By means of IR measurements, we follow the reaction and determine the kinetics and the quantum yield. The photoproducts are isolated by HPLC and characterized by 1H-NMR whose results confirm the formation of the ortho derivative as the most probable one and we estimate the degree of conversion of the reaction. High-level quantum mechanical calculations both in gas and solvated phase are employed to strongly support the interpretation of the experimental results, and assess the reaction product.

Thiophene-benzothiadiazole based donor–acceptor–donor (D-A-D) bolaamphiphiles, self-assembly and photophysical properties

Bolaamphiphilies with D-A-D type π-conjugated rigid cores composed by thiophenes as donors (D) and benzothiadiazole (BTD) as central acceptor (A) have been synthesised. Their self-assemblies and photophysical properties were investigated by polarising optical microscope, differential scanning calorimetry, X-ray diffraction and scanning electron microscopy. Such compounds can self-assemble into honeycomb cylinder mesophases with Colhex?/p6mm and Colsqu/p4mm lattices in their pure states as well as organogels with different morphologies in organic solvents. Their absorption spectra cover nearly the entire visible light range and their band gaps are relatively low. Tetrathiophene BTD based bolaamphilphiles (BT4/n) with higher D/A ratios than the bisthiophene BTD bolaamphilphiles (BT2/n) can self-assemble into more ordered nanostructures in both bulk states and solution. Both the absorption and emission peaks of BT4/n are strongly red shifted. The influence of the molecular conformation, the conjugated core length, as well as the D/A ratio on the self-assemble and photophysical characteristics of such D-A-D bolaamphiphiles are discussed.

A Series of 2,5-Bis(5-aryl-2-thienyl)pyrazines with a Linear-Shaped (D-π)2-A System: Synthesis and study of the optical properties including fluorosolvatochromism and proton-base-sensing

A series of 2,5-bis(5-aryl-2-thienyl)pyrazines with distinct optical properties tuned by the intramolecular charge transfer (ICT) degree based on the donor strength of the aryl groups have been synthesized. It was found that 2,5-bis[5-(4-N,N-dibutyl-amino

Benzothiadiazole-based D-π-A-π-D fluorophores: Synthesis, self-assembly, thermal and photophysical characterization

A symmetrical linear D-π-A-π-D hexacatenar compound with 2,1,3-benzothiadiazole as the acceptor core connected at its 4,7 position with phenylthienylethynyl spacers has been designed and synthesized. This compound displays liquid crystalline property with oblique columnar mesophase and forms an organogel in dichloromethane. The investigation of photophysical and electrochemical properties reveals that this compound can exhibit broad and strong absorption band at the range of 300–700 nm with a low energy gap in solid state, meanwhile it exhibits highly red fluorescent emission and large Stokes shifts.

An efficient protocol for the palladium-catalysed Suzuki-Miyaura cross-coupling

The palladacyclic catalyst precursor received by ortho-palladation of ([1,1′-biphenyl]-2-yloxy)diisopropyl-phosphine represents a highly active system for Suzuki-Miyaura cross-coupling reactions when used in neat water. An efficient, broadly applicable and sustainable aqueous protocol was developed using 2.5 eq. of Na2CO3 as base, allowing the reaction to be performed under air and at ambient temperature with Pd loadings of 0.04 mol%. Coupling products are obtained in high yields and excellent purity by simple filtration with no organic solvents needed throughout the whole reaction. A broad variety of functional groups are tolerated and a large number of substrates can be applied with this protocol. The crystal structure of the palladacyclic catalyst precursor is presented as well as investigations targeting the nature of catalyst activation and the active catalytic species.

Facile palladium catalyzed Suzuki-Miyaura coupling in air and water at ambient temperature

A new palladacyclic catalyst yields high activities in aqueous Suzuki-Miyaura coupling at room temperature. Using an optimized protocol, a broad range of products can be isolated in good to excellent yields and high purity by simple filtration.

Discovery of Potent, Selective, and Orally Active Carboxylic Acid Based Inhibitors of Matrix Metalloproteinase-13

The matrix metalloproteinase enzyme MMP-13 plays a key role in the degradation of type II collagen in cartilage and bone in osteoarthritis (OA). An effective MMP-13 inhibitor would therefore be a novel disease modifying therapy for the treatment of arthritis. Our efforts have resulted in the discovery of a series of carboxylic acid inhibitors of MMP-13 that do not significantly inhibit the related MMP-1 (collagenase-1) or tumor necrosis factor-α (TNF-α) converting enzyme (TACE). It has previously been suggested (but not proven) that inhibition of the latter two enzymes could lead to side effects. A promising carboxylic acid lead 9 was identified and a convergent synthesis developed. This paper describes the optimization of 9 and the identification of a compound 24f for further development. Compound 24f is a subnanomolar inhibitor of MMP-13 (IC50 value 0.5 nM and Ki of 0.19 nM) having no activity against MMP-1 or TACE (IC50 of >10000 nM). Furthermore, in a rat model of MMP-13-induced cartilage degradation, 24f significantly reduced proteoglycan release following oral dosing at 30 mg/kg (75% inhibition, p 0.05) and at 10 mg/kg (40% inhibition, p 0.05).

A convergent synthesis of AR-C123196 utilising reaction between a cyclic carbonate and a phenol for aryl alkyl ether formation

The development of a convergent synthesis of AR-C123196 is reported in which the alkyl aryl ether linkage was formed by nucleophilic attack of a phenolic hydroxyl group onto a cyclic carbonate. This approach was successfully operated on a multikilogram sc

BIARYL SUBSTITUTED HETEROCYCLE INHIBITORS OF LTA4H FOR TREATING INFLAMMATION

The present invention relates to a chemical genus of biaryl substituted heterocycle inhibitors of LTA4H (leukotriene A4 hydrolase) useful for the treatment and prevention and prophylaxis of inflammatory diseases and disorders. The compounds have general formula Ψ: An example is

Piperazine compounds as inhibitors of MMP or TNF

A compound of formula (I) wherein A is a sulfonyl or a carbonyl; R1is an optionally substituted aryl, an optionally substituted heterocyclic group, an optionally substituted lower alkyl or an optionally substituted lower alkenyl; R2is a hydrogen, an optionally substituted lower alkyl, an optionally substituted aryl or an optionally substituted heterocyclic group; R3is an optionally substituted lower alkyl, an optionally substituted lower alkoxy, an optionally substituted aryloxy, an optionally substitued lower alkenyl, an optionally substituted aryl, an optionally substituted heterocyclic group or an optionally substitued amino; R4is a hydrogen, an optionally substituted lower alkyl, an optionally substituted aryl or an optionally substituted heterocyclic group; R5is a hydrogen, an optionally substituted lower alkyl, an optionally substituted aryl or an optionally substituted heterocyclic group; and R10is a hydroxy or a protected hydroxy, and a pharmaceutically acceptable salt thereof. The compound of the present invention is useful as a medicament for prophylactic and therapeutic treatment of MMP- or TNFα-mediated diseases.