52629-46-6Relevant academic research and scientific papers
Design and Synthesis of Bioisosteres of Acylhydrazones as Stable Inhibitors of the Aspartic Protease Endothiapepsin
Jumde, Varsha R.,Mondal, Milon,Gierse, Robin M.,Unver, M. Yagiz,Magari, Francesca,van Lier, Roos C. W.,Heine, Andreas,Klebe, Gerhard,Hirsch, Anna K. H.
, p. 2266 - 2270 (2018)
Acylhydrazone-based dynamic combinatorial chemistry (DCC) is a powerful strategy for the rapid identification of novel hits. Even though acylhydrazones are important structural motifs in medicinal chemistry, their further progression in development may be
Structural insight into the optimization of ethyl 5-hydroxybenzo[g]indol-3-carboxylates and their bioisosteric analogues as 5-LO/m-PGES-1 dual inhibitors able to suppress inflammation
Bruno, Ferdinando,Errico, Suann,Pace, Simona,Nawrozkij, Maxim B.,Mkrtchyan, Arthur S.,Guida, Francesca,Maisto, Rosa,Olga?, Abdurrahman,D'Amico, Michele,Maione, Sabatino,De Rosa, Mario,Banoglu, Erden,Werz, Oliver,Fiorentino, Antonio,Filosa, Rosanna
, p. 946 - 960 (2018/07/24)
The release of pro-inflammatory mediators, such as prostaglandines (PGs) and leukotrienes (LTs), arising from the arachidonic acid (AA) cascade, play a crucial role in initiating, maintaining, and regulating inflammatory processes. New dual inhibitors of 5-lipoxygenase (5-LO) and microsomal prostaglandin E2 synthase-1 (mPGES-1), that block, at the same time, the formation of PGE2 and LTs, are currently emerged as a highly interesting drug candidates for better pharmacotherapie of inflammation-related disorders. Following our previous studies, we here performed a detailed structure-based design of benzo[g]indol-3-carboxylate derivatives, disclosing several new key factors that affect both enzyme activity. Ethyl 2-(3,4-dichlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate (4b, RAF-01) and ethyl 2-(3,4-dichlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate (7h, RAF-02) emerged as the most active compounds of the series. Additionally, together with selected structure based analogues, both derivatives displayed significant in vivo anti-inflammatory properties. In conclusion, modeling and experimental studies lead to the discovery of new candidate compounds prone to further developments as multi-target inhibitors of the inflammatory pathway.
A 2, 4, 6 - trimethyl benzene acetyl chloride synthesis process (by machine translation)
-
Paragraph 0059-0081, (2017/04/03)
The invention discloses a method for preparing 2, 4, 6 - trimethyl benzene acetyl chloride new synthesis process, the synthesis process is introduced into the low-boiling point solvent, change the 2, 4, 6 - trimethyl benzene acetic acid and the number of
A 2, 4, 6-Trimethylbenzene acetyl chloride synthesis process
-
, (2017/02/09)
The invention relates to a synthesis technology for 2, 4, 6-trimethylbenzene acetyl chloride, comprising the following steps of: putting thionyl chloride, a catalyst and 2, 4, 6-trimethylbenzene acetic acid into a reaction kettle in batches, and controlling temperature to carry out reaction; and after the reaction, distilling (high vacuum) in a heating way in the reaction kettle, and acquiring a final product. The preparation method of the 2, 4, 6-trimethylbenzene acetic acid can comprise the following steps of: carrying out chloromethylation reaction by taking trimethylbenzene, formaldehyde and concentrated hydrochloric acid as raw materials, adding toluene to extract after reacting, and washing to obtain a toluene solution of 2, 4, 6-trimethyl benzyl chloride; taking the toluene solution of 2, 4, 6-trimethyl benzyl chloride and the sodium cyanide as raw materials, adding a phase transfer catalyst, reflowing in a heating way to carry out cyanation reaction, washing by adding water after reacting, distilling oil phase to recover toluene and mesitylene, and rectifying to obtain 2, 4, 6-trimethylbenzene acetonitrile; and hydrolyzing the 2, 4, 6-trimethylbenzene acetonitrile, centrifuging to obtain a 2, 4, 6-trimethylbenzeneacetic acid crude product, and optionally selecting and carrying out the aftertreatment to obtain the 2, 4, 6-trimethylbenzeneacetic acid. The content of the 2, 4, 6-trimethylbenzene acetyl chloride synthesized by the method disclosed by the invention is more than or equal to 98.0%, and the content of the 2, 4, 6-trimethylbenzene acetonitrile is less than or equal to 0.5%.
3'-ALKOXYSPIROCYCLOPENTYL-SUBSTITUTED TETRAMIC AND TETRONIC ACIDS
-
Page/Page column 51, (2010/02/16)
The invention relates to novel compounds of the formula (I) in which W, X, Y, Z, A, B, D, Q1, Q2 and G are as defined above, to a plurality of processes for their preparation and to their use as pesticides and/or herbicides and/or fu
3-aryl-tetronic acid derivatives, the production thereof and the use thereof as antiparasitic agents
-
, (2008/06/13)
The present invention relates to new 3-aryl-4-hydroxy-Δ3 -dihydrofuranone derivatives of the formula (I) STR1 in which A and B together with the carbon atom to which they are bonded form an unsubstituted or substituted 5- to 7-membered ring which is interrupted by at least one hetero atom, X represents alkyl, halogen or alkoxy, Y represents hydrogen, alkyl, halogen, alkoxy or halogenoalkyl, Z represents alkyl, halogen or alkoxy, n represents a number 0, 1, 2 or 3, G represents hydrogen (a) or one of the groups STR2 E represents a metal Ion equivalent or an ammonium ion, L represents oxygen or sulphur, M represents oxygen or sulphur and R1, R2, R3, R4, R5, R6 and R7 have the meanings given in the description, to processes for their preparation, and to their use as pesticides.
Diverse photochemistry of sterically congested α-arylacetophenones: ground-state conformational control of reactivity
Wagner, Peter J.,Zhou, Boli,Hasegawa, Tadashi,Ward, Donald L.
, p. 9640 - 9654 (2007/10/02)
The effects of α and ortho substituents on the photoreactivity of various α-(o-tolyl)- and α-mesitylacetophenones have been measured. In general, both types of substitution lower the efficiency of cyclization to 2-indanol derivatives in solution. 1,3-Rearrangement of an α-mesityl group to group to form enol ethers and α-cleavage to radicals compete to various degrees, in some cases becoming dominant. Quenching studies in solution show that all three reactions occur from the same n,π* triplet state; α-substitution lowers rate constants for δ-hydrogen abstraction and increases those for α-cleavage and 1,3-rearrangement. X-ray crystal analysis and MMX calculations both show that any additional substitution at the α-carbon of α-aryl (phenyl, tolyl, or mesityl) ketones favors conformers in which the α-aryl group have rotated 120° away from eclipsing the carbonyl. In agreement with this, α-phenyl and α-(o-tolyl) ketones undergo γ-hydrogen abstraction (Norrish type II reaction) with rate constants almost as large as those of the nonarylated ketones. NMR line-broadening studies show that, in most of the α-mesityl ketones, the rate constants for rotation around the mesityl-α-carbon bond (104-106 s-1) are much slower than triplet decay. The same is true for rotations around the carbonyl-α-carbon bond in the α-arylisobutyrophenones. Considered of the spectroscopic evidence, triplet lifetimes, and calculated rotational barriers indicates that ground-state conformational preferences determine which excited-state reactions can occur in most of these ketones. Many of the ketones that cyclize in low yield in solution do so in much higher yield when irradiated as solids, presumably because α-cleavage to radicals becomes mostly revertible. The solid-state reactivity demonstrates that hydrogen abstraction can occur from what are supposedly nonideal geometries; in particular, large values (60-70°) for the dihedral angle and rate constants for hydrogen abstraction in solution plane of the carbonyl π system. The relationship between this angle and rate constants for hydrogen abstraction in solution is discussed. Rate constants for α-cleavage reveal the separate influences of steric congestion and conjugation of the developing benzyl radicals. The 1,3-aryl migration to oxygen appears to arise from initial CT complexation of the α-aryl to the carbonyl; subsequent bonding of oxygen to the benzene ring apparently relieves steric congestion. The 50:50 initial mixture of Z and E enol ethers suggests that the rearrangement is adiabatic, generating enol ether in its twisted triplet state. A large enhancement of indanol yields by alcoholic solvents is suggested to involve protonation of the same CT complex.
