39889-69-5Relevant academic research and scientific papers
Ultrafast UV-Vis and IR studies of p-biphenylyl acetyl and carbomethoxy carbenes
Wang, Jin,Burdzinski, Gotard,Kubicki, Jacek,Platz, Matthew S.
, p. 11195 - 11209 (2008)
The photochemistry of a p-biphenylyl diazo ester (BpCN2CO 2CH3) and diazo ketone (BpCN2COCH3) were studied by ultrafast time-resolved UV-vis and IR spectroscopies. The excited states of these diazo compounds were detected and found to decay with lifetimes of less than 300 fs. The diazo ester produces singlet carbene with greater quantum efficiency than the ketone analogue due to competing Wolff rearrangement (WR) in the excited state of the diazo ketone. Carbene BpCCO 2CH3 has a singlet-triplet gap that is close to zero in cyclohexane, but the triplet is the ground state. The two spin states are in rapid equilibrium in this solvent relative to reaction with cyclohexane. There is (for a carbene) a slow rate of singlet to triplet intersystem crossing (isc) in this solvent because the orthogonal singlet must rotate to a higher energy orientation prior to isc. In acetonitrile and in dichloromethane BpCCO 2CH3 has a singlet ground state. Ketocarbene BpCCOCH 3 has a singlet ground state in cyclohexane, in dichloromethane, and in acetonitrile and decays by WR to form a ketene detected by ultrafast IR spectroscopy in these solvents. Ketocarbenes have more stable singlet states, relative to carbene esters, because of the superior conjugation of the filled hybrid orbital of the carbene with the π system of the carbonyl group, the same factor that makes methyl ketones more acidic than the analogous esters. The rate of WR of BpCCOCH3 is faster in cyclohexane than in dichloromethane and acetonitrile because of intimate solute-solvent interactions between the empty p orbital of the carbene and nonbonding electron pairs of heteroatoms of the solvent. These interactions stabilize the carbene and retard the rate of WR.
Cesium ion pair acidities of some N,N-dialkylacetamides and aggregation of their cesium enolates in tetrahydrofuran
Krom, James A.,Streitwieser, Andrew
, p. 6354 - 6359 (1996)
Cesium ion pair acidities are reported of some N,N-dialkylacetamides at 25°C in tetrahydrofuran. The cesium enolates of α-arylacetamides are essentially monomeric at concentrations of about 10-4 M, but small amounts of dimers are present for the enolates of N,N-dimethyl- and N,N-diethyl(4-biphenylyl)acetamide (Kdimer is approximately 400 M-1). The cesium enolate of N,N-dimethyldiphenylacetamide forms small amounts of dimers, but the dimerization constant of -1 is near the limit of detection of our methods. The enolate of N,N-diethylacetamide has an average aggregation number of 3.3, consistent with a mixture of dimers and tetramers. The cesium ion pair pKs of the α-arylacetamides are about 25-26, and that of N,N-diethylacetamide is greater than 33.7. The acidity data are in good agreement with measurements that have been reported in the literature for similar systems.
Base-catalyzed deuterium and tritium labelling of 1-biphenyl-4-ylpropane-1, 2-dione and deuteration of aryl methyl ketones
Berthelette, Carl,Scheigetz, John
, p. 891 - 894 (2004)
A synthesis and a base-catalyzed exchange reaction was developed under mild conditions to deuterate and subsequently tritiate the methyl group of the base sensitive diketone 1-biphenyl-4-ylpropane-1,2-dione depicted in Figure 1. Using Et3N as b
Synthesis and evaluation of benzenesulfonic acid derivatives as human neutrophil elastase (hNE) inhibitors
Xu, Yanzhao,Qi, Na,Wen, Hui,Zhang, Gang,Wang, Yuchen,Cui, Huaqing
, p. 387 - 398 (2021/01/15)
Herein we report our investigation concerning the development of Human neutrophil elastase (hNE) inhibitors for the treatment of Acute Respiratory Distress Syndrome (ARDS). Various benzenesulfonic acid derived compounds were synthesized and evaluated as competitive inhibitors of hNE. Biological screening revealed that compound 4f shows moderate inhibitory activity (IC50 = 35.2 μM) against hNE. Compound 4f was also superimposed onto the active center of hNE to understand the binding mode.
CEPHALOSPORIN CIPROFLOXACIN HYBRID COMPOUNDS
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Page/Page column 35; 39; 41, (2020/06/05)
A compound of formula (Ia) and related aspects.
Preparation method of neprilysin inhibitor intermediate
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Paragraph 0021-0022, (2020/10/04)
The invention discloses a preparation method for an enkephalinase inhibitor intermediate. According to the preparation method, a target compound with a formula I as described in the specification is prepared by using a compound as shown in a formula IV which is described in the specification as an initial material through a reaction with few steps, wherein the compound with the formula I can be used for preparation of an enkephalinase inhibitor drug namely Sacubtril. In the formula I and the formula IV, R is selected from the group consisting of H, methyl, ethyl or other lower alkyl.
N-monoarylacetothioureas as potent urease inhibitors: synthesis, SAR, and biological evaluation
Fang, Hai-Lian,He, Jie-Ling,Li, Wei-Yi,Liu, Shan-Shan,Ni, Wei-Wei,Pan, Xing-Ming,Xiao, Zhu-Ping,Ye, Ya-Xi,Yi, Juan,Zhou, Mi,Zhou, Tian-Li,Zhu, Hai-Liang
, p. 404 - 413 (2020/01/03)
A urease inhibitor with good in vivo profile is considered as an alternative agent for treating infections caused by urease-producing bacteria such as Helicobacter pylori. Here, we report a series of N-monosubstituted thioureas, which act as effective urease inhibitors with very low cytotoxicity. One compound (b19) was evaluated in detail and shows promising features for further development as an agent to treat H. pylori caused diseases. Excellent values for the inhibition of b19 against both extracted urease and urease in intact cell were observed, which shows IC50 values of 0.16 ± 0.05 and 3.86 ± 0.10 μM, being 170- and 44-fold more potent than the clinically used drug AHA, respectively. Docking simulations suggested that the monosubstituted thiourea moiety penetrates urea binding site. In addition, b19 is a rapid and reversible urease inhibitor, and displays nM affinity to urease with very slow dissociation (koff=1.60 × 10?3 s?1) from the catalytic domain.
Visible-Light-Assisted Gold-Catalyzed Fluoroarylation of Allenoates
Feng, Chao,Tang, Hai-Jun,Zhang, Xinggui,Zhang, Yu-Feng
supporting information, p. 5242 - 5247 (2020/02/28)
A strategically novel synthetic method for the fluoroarylation of allenic ester was developed that enables the expedient construction of a host of β-fluoroalkyl-containing cinnamate derivatives. The reaction proceeds through visible-light-promoted gold redox catalysis, occurs smoothly under very mild reaction conditions, accommodates a large variety of functional groups, and more importantly allows the incorporation of fluorine and aryl groups with excellent regio- and stereoselectivity. The concomitant activation mode for both the allene motif and the hydrogen fluoride is key for the success of the reaction.
Cobalt(II)-Catalyzed Stereoselective Olefin Isomerization: Facile Access to Acyclic Trisubstituted Alkenes
Zhang, Sheng,Bedi, Deepika,Cheng, Lu,Unruh, Daniel K.,Li, Guigen,Findlater, Michael
supporting information, p. 8910 - 8917 (2020/12/23)
Stereoselective synthesis of trisubstituted alkenes is a long-standing challenge in organic chemistry, due to the small energy differences between E and Z isomers of trisubstituted alkenes (compared with 1,2-disubstituted alkenes). Transition metal-catalyzed isomerization of 1,1-disubstituted alkenes can serve as an alternative approach to trisubstituted alkenes, but it remains underdeveloped owing to issues relating to reaction efficiency and stereoselectivity. Here we show that a novel cobalt catalyst can overcome these challenges to provide an efficient and stereoselective access to a broad range of trisubstituted alkenes. This protocol is compatible with both mono- and dienes and exhibits a good functional group tolerance and scalability. Moreover, it has proven to be a useful tool to construct organic luminophores and a deuterated trisubstituted alkene. A preliminary study of the mechanism suggests that a cobalt-hydride pathway is involved in the reaction. The high stereoselectivity of the reaction is attributed to both a π-πstacking effect and the steric hindrance between substrate and catalyst.
Studies and synthesis of substituted 4-biphenyl acetamide derivatives
Khullar, Anju
, p. 510 - 514 (2019/02/06)
A new series of substituted 4-biphenylamides have been synthesized by condensation of 4-biphenyl acetic acid with different primary amines (aromatic and aliphatic). 4-Biphenyl acetic acid was first treated with thionyl chloride in dry benzene to prepare substituted 4-biphenyl acetyl chloride, which is then treated with different aliphatic or aromatic amines to synthesize various substituted 4-biphenyl acid-amide derivatives. The structure of newly synthesized compounds has been established by analytical and spectral methods. These synthesized compounds have shown antifungal properties against Fusarium udum and Curvularia lunata.
