13679-70-4Relevant articles and documents
Synthesis and biological evaluation of thiophene [3,2-b] pyrrole derivatives as potential anti-inflammatory agents
Rajender Kumar,Raju,Satish Goud,Sailaja,Sarma,Om Reddy,Prem Kumar,Krishna Reddy,Suresh,Hegde, Pragathi
, p. 1221 - 1230 (2004)
A series of thiophene [3,2-b] pyrrole derivatives were synthesized and evaluated their abilities to inhibit anti-inflammatory activity. In this series, substituent effects at the N-1, 2 and 5 positions of thiophene [3,2-b] pyrrole were examined. The results obtained are compared to those previously reported anti-inflammatory drugs like Tenidap sodium, Diclofenac sodium and Piroxicam. The results indicated the critical role of the group linked in the N-1 position and 2, 5 positions of thiophene [3,2-b] pyrrole with different functional groups.
Tunable spectroscopic and electrochemical properties of conjugated push-push, push-pull and pull-pull thiopheno azomethines
Dufresne, Stephane,Bourgeaux, Marie,Skene
, p. 1166 - 1177 (2007)
Novel azomethines consisting uniquely of thiophene units were examined. The highly conjugated compounds were prepared by condensing air stable aminothiophenes with 2-thiophene aldehydes, which were substituted with various electronic groups. The resulting azomethines are highly conjugated and are both reductively and hydrolytically resistant. Various electron donating and accepting groups placed in the 2-position of 5-thiophene carboxaldehyde lead to electronically delocalized push-push, pull-pull, and push-pull azomethines. These electronic groups affect both the HOMO and the LUMO levels, which influence the absorption and emission spectra. Colors spanning the entire visible spectrum ranging from yellow to blue are possible with these nitrogen containing conjugated compounds. Excited state deactivation of the singlet excited state occurs predominately by internal conversion while only a small amount of energy is dissipated by intersystem crossing to the triplet state and by fluorescence. The ensuing fluorescence and phosphorescence of the thiopheno azomethines are similar to those of their thiophene analogues currently used in functional devices, but with the advantage of a low triplet state and tunable HOMO-LUMO energy levels extending from 3.0 to 1.9 eV. Quasi-reversible electrochemical radical cation formation is possible while the oxidation potential is dependent on the nature of the electronic group appended to the thiophene. The crystallographic data of the electronic push-push system show the azomethine bonds are planar and linear and they adopt the E isomer. The Royal Society of Chemistry 2007.
Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal
Zhan, Huan,Cui, Heping,Yu, Junhe,Hayat, Khizar,Wu, Xian,Zhang, Xiaoming,Ho, Chi-Tang
, (2021/09/28)
The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r
Preparation method of 5-methylthiophene-2-carboxaldehyde
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Paragraph 0028-0041, (2021/03/31)
The invention relates to a preparation method of 5-methylthiophene-2-carboxaldehyde. The method comprises the following steps: putting N, N-dimethylformamide into a container at about 10-15 DEG C, carrying out low-temperature treatment for 1-2 hours for later use, putting 2-methylthiophene into an environment with the pH value of 7-8.5 at normal temperature, performing treating for 1-4 hours for later use, and slowly dropwise adding the treated 2-methylthiophene into the container filled with N, N-dimethylformamide; performing heating to 45-60 DEG C, fully performing stirring, carrying out heat preservation reaction for 3-5 hours, and absorbing tail gas generated in the reaction process with sodium hydroxide. Briefly speaking, according to the technical scheme, an excellent optimization scheme is utilized, and the problems existing in preparation of 5-methylthiophene-2-carboxaldehyde are solved.
Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses
Liang, Fengying,Eda, Kazuo,Okazoe, Takashi,Wada, Akihiro,Mori, Nobuaki,Konishi, Katsuhiko,Tsuda, Akihiko
, p. 6504 - 6517 (2021/05/06)
The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.
Rhenium-Catalyzed Reduction of Carboxylic Acids with Hydrosilanes
Wei, Duo,Buhaibeh, Ruqaya,Canac, Yves,Sortais, Jean-Baptiste
supporting information, p. 7713 - 7716 (2019/10/10)
Re2(CO)10 efficiently catalyzes the direct reduction of various carboxylic acids under mild conditions (rt, irradiation 350 or 395 nm). While aliphatic carboxylic acids were readily converted to the corresponding disilylacetals with low catalyst loading (0.5 mol %) in the presence of Et3SiH (2.2 equiv), aromatic analogues required more drastic conditions (Re2(CO)10 5 mol %, Ph2MeSiH 4.0 equiv) to afford the corresponding aldehydes after acid treatment.
Palladium-catalyzed C-H formylation of electron-rich heteroarenes through radical dichloromethylation
Bao, Yan,Wang, Jian-Yong,Zhang, Ya-Xuan,Li, Yan,Wang, Xi-Sheng
supporting information, p. 3147 - 3150 (2018/07/13)
A novel palladium-catalyzed C-H formylation of electron-rich N-, O-, and S-containing heteroarenes has been developed. The key to success is that the commercially available BrCHCl2 was used as a stoichiometric carbonyl source. Mechanistic investigations indicated that different from the known Reimer-Tiemann reaction, this net C-H formylation proceeded through an electrophilc radical-type path.
Reduction of N,N-Dimethylcarboxamides to Aldehydes by Sodium Hydride–Iodide Composite
Chan, Guo Hao,Ong, Derek Yiren,Yen, Zhihao,Chiba, Shunsuke
, (2018/05/14)
A new and concise protocol for selective reduction of N,N-dimethylamides into aldehydes was established using sodium hydride (NaH) in the presence of sodium iodide (NaI) under mild reaction conditions. The present protocol with the NaH-NaI composite allows for reduction of not only aromatic and heteroaromatic but also aliphatic N,N-dimethylamides with wide substituent compatibility. Retention of α-chirality in the reduction of α-enantioriched amides was accomplished. Use of sodium deuteride (NaD) offers a new step-economical alternative to prepare deuterated aldehydes with high deuterium incorporation rate. The NaH-NaI composite exhibits unique chemoselectivity for reduction of N,N-dimethylamides over ketones.
Systematic structure-activity relationship (SAR) exploration of diarylmethane backbone and discovery of a highly potent novel uric acid transporter 1 (URAT1) inhibitor
Cai, Wenqing,Wu, Jingwei,Liu, Wei,Xie, Yafei,Liu, Yuqiang,Zhang, Shuo,Xu, Weiren,Tang, Lida,Wang, Jianwu,Zhao, Guilong
, (2018/02/07)
In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a-1x and 1ha-1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly potent novel URAT1 inhibitor, 1h, which was 200-and 8-fold more potent than parent lesinurad and benzbromarone, respectively (IC50 = 0.035 μM against human URAT1 for 1h vs. 7.18 μM and 0.28 μM for lesinurad and benzbromarone, respectively). Compound 1h is the most potent URAT1 inhibitor discovered in our laboratories so far and also comparable to the most potent ones currently under development in clinical trials. The present study demonstrates that the diarylmethane backbone represents a very promising molecular scaffold for the design of potent URAT1 inhibitors.
Candida parapsilosis ATCC 7330 mediated oxidation of aromatic (activated) primary alcohols to aldehydes
Sivakumari, Thakkellapati,Chadha, Anju
, p. 91594 - 91600 (2015/11/10)
A green, simple and high yielding [up to 86% yield] procedure is developed for the oxidation of aromatic (activated) primary alcohols to aldehydes using whole cells of Candida parapsilosis ATCC 7330. The biotransformation is carried out under mild conditions at 25 °C, in hexane: water (48 : 2) (v/v).
