108577-34-0Relevant articles and documents
Design, synthesis, biological evaluation and in silico study of benzyloxybenzaldehyde derivatives as selective aldh1a3 inhibitors
Ibrahim, Ali I. M.,Ikhmais, Balqis,Batlle, Elisabet,Abuharb, Waed K.,Jha, Vibhu,Jaradat, Khaled T.,Jiménez, Rafael,Pequerul, Raquel,Parés, Xavier,Farrés, Jaume,Pors, Klaus
, (2021/09/28)
Aldehyde dehydrogenase 1A3 (ALDH1A3) has recently gained attention from researchers in the cancer field. Several studies have reported ALDH1A3 overexpression in different cancer types, which has been found to correlate with poor treatment recovery. Theref
Crystal engineering of hand-twisted helical crystals
Saha, Subhankar,Desiraju, Gautam R.
, p. 1975 - 1983 (2017/02/15)
A strategy is outlined for the design of hand-twisted helical crystals. The starting point in the exercise is the one-dimensional (1D) plastic crystal, 1,4-dibromobenzene, which is then changed to a 1D elastic crystal, exemplified by 4-bromophenyl 4'-chlorobenzoate, by introduction of a molecular synthon -O-CO-in lieu of the supramolecular synthon Br···Br in the precursor. The 1D elastic crystals are next modified to two-dimensional (2D) elastic crystals, of the type 4-bromophenyl 4'-nitrobenzoate where the halogen bonding and C-H· · ·O hydrogen bonding are well-matched. Finally, varying the interaction strengths in these 2D elastic crystals gives plastic crystals with two pairs of bendable faces but without slip planes. Typical examples are 4-chlorophenyl and 4-bromophenyl 4'-nitrobenzoate. This type of 2D plasticity represents a new type of bendable crystals in which plastic behavior is seen with a fair degree of isotropic character in the crystal packing. The presence of two sets of bendable faces, generally orthogonal to each other, allows for the possibility of hand-twisting of the crystals to give grossly helical morphologies. Accordingly, we propose the name hand-twisted helical crystals for these substances.
Design, synthesis and evaluation of rhodanine derivatives as aldose reductase inhibitors
Agrawal, Yogesh P.,Agrawal, Mona Y.,Gupta, Arun K.
, p. 172 - 180 (2015/01/30)
Aldose reductase (ALR) enzyme plays a significant role in conversion of excess amount of glucose into sorbitol in diabetic condition, inhibitors of which decrease the secondary complication of diabetes mellitus. To understand the structural interaction of inhibitors with ALR enzyme and develop more effective ALR inhibitors, a series of substituted 5-phenylbenzoate containing N-substituted rhodanine derivatives were synthesized and evaluated for their in vitro ALR inhibitory activity. Docking studies of these compounds were carried out, which revealed that the 5-phenylbenzoate moiety deeply influenced the key π-π stacking while 4-oxo-2-thioxothiazolidines contributed in hydrogen bond interactions. The phenyl ring of benzylidene system occupied in specific pocket constituted from Phe115, Phe122, Leu300 and Cys303 while the rhodanine ring forms a tight net of hydrogen bond with Val47 at anionic binding site of the enzyme. The structural insights obtained from the docking study gave better understanding of rhodanine and macromolecular interaction and will help us in further designing and improving of ALR inhibitory activity of rhodanine analogs. Series of substituted 5-phenylbenzoate rhodanine analogs were synthesized and evaluated for their ALR inhibitory activity. The docking study of synthesized compounds was carried out, which revealed that the 5-phenylbenzoate moiety deeply influenced the key π-π stacking while 4-oxo-2-thioxothiazolidines contributed in hydrogen bond interactions.
Imidazo[2,1-b]thiazepines: Synthesis, structure and evaluation of benzodiazepine receptor binding
Kiec-Kononowicz, Katarzyna,Karolak-Wojciechowska, Janina,Michalak, Barbara,Pekala, Elzbieta,Schumacher, Britta,Mueller, Christa E.
, p. 205 - 218 (2007/10/03)
As a continuation of our search for new ligands acting on benzodiazepine receptors among the fused 2-thiohydantoin derivatives, a series of 5-substituted imidazo[2,1-b]thiazepines was synthesized and investigated in radioligand binding studies at the benz
Chemical modification of coumarin dimer and HIV-1 integrase inhibitory activity
Mao, Pili Chih-Min,Mouscadet, Jean-Francois,Leh, Herve,Auclair, Christian,Hsu, Ling-Yih
, p. 1634 - 1637 (2007/10/03)
A systematic series of chemically modified coumarin dimmers has been synthesized and tested for their inhibitory activity against HIV-1 integrase. We observed that modified coumarin dimmers containing hydrophobic moiety on the linker display potent inhibi
(Aryloxy)aryl semicarbazones and related compounds: A novel class of anticonvulsant agents possessing high activity in the maximal electroshock screen
Dimmock, Jonathan R.,Puthucode, Ramanan N.,Smith, Jennifer M.,Hetherington, Mark,Quail, J. Wilson,Pugazhenthi, Uma,Lechler, Terry,Stables, James P.
, p. 3984 - 3997 (2007/10/03)
A number of (aryloxy)aryl semicarbazones and related compounds were synthesized and evaluated far anticonvulsant activities. After intraperitoneal injection to mice, the semicarbazones were examined in the maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ), and neurotoxicity (NT) screens. The results indicated that greater protection was obtained in the MES test than the scPTZ screen. Quantitation of approximately one-third of the compounds revealed an average protection index (PI, i.e. TD50/ED50) of approximately 9. After oral administration to rats, a number of compounds displayed significant potencies in the MES screen (ED50 of 1-5 mg/kg) accompanied by very high protection indices. In fact over half the compounds had PI figures of greater than 100, and two were in excess of 300. The compounds were essentially inactive in the scPTZ and NT screens after oral administration to rats. Various compounds displayed greater potencies and PI figures in the mouse intraperitoneal and rat oral screens than three reference clinically used drugs. The data generated supported a binding site hypothesis. Quantitative structure-activity relationships indicated a number of physicochemical parameters which contributed to activity in the MES screen. X-ray crystallography of five compounds suggested the importance of certain interatomic distances and bond angles for activity in the mouse and rat MES screens.
Effects of Branching of the Ester Alkyl Chain on the Mesomorphic Properties of Alkyl 4-benzoates
Matsuzaki, Hiroyuki,Matsunaga, Yoshio
, p. 2300 - 2305 (2007/10/02)
The mesomorphic properties of five homologous series of alkyl 4-benzoates, where X=CN, NO2, CH3, Cl, and CH3COO, have been studied.The ester alkyl groups employed were the following eleven types: ethyl and p
