111233-69-3Relevant articles and documents
Synthesis, structure and magnetic properties of oligometallic systems derived from di- and trinuclear copper(ii) amido-oximate complexes
Kolotilov, Sergey V.,Schollmeyer, Dieter,Thompson, Laurence K.,Golub, Vladimir,Addison, Anthony W.,Pavlishchuk, Vitaly V.
, p. 3007 - 3014 (2008)
Three heterometallic complexes [M(H2O)n][Cu 3L2(H2O)] (M = Mn2+, Co2+ or Ba2+) and one dinuclear compound (CuDien)(CuL{H2O}) were prepared by interaction of anionic compounds Cu3L 22- or CuL2- with the corresponding cations (H4L = 1,9-dicyano-1,9-bis(hydroximino)-3,7-diazanonane-2,8-dione; Dien = 1,5-diamino-3-azapentane). The complexes [M(H2O) n][Cu3L2(H2O)] have a polymeric structure, formed via oligomerization of Cu3L2 2- units and additionally, in the case of the Ba-salt, by binding of Cu3L22- units through Ba2+. Antiferromagnetic interactions occur in all the complexes, while for [Co(H 2O)6][Cu3L2(H2O)] there is evidence of some ferromagnetic ordering at low temperatures. The values of J are lower in magnitude than for similar, previously reported systems, which is attributed to the electron-withdrawing effect of the ligand cyano groups. The Royal Society of Chemistry 2008.
Tyrphostins. 6. Dimeric benzylidenemalononitrile tyrphostins: Potent inhibitors of EGF receptor tyrosine kinase in vitro
Gazit, Aviv,Osherov, Nir,Gilon, Chaim,Levitzki, Alexander
, p. 4905 - 4911 (1996)
Benzylidenemalononitrile (BMN) tyrphostins were previously found to be potent inhibitors of EGF receptor (EGFR) tyrosine kinase activity. Since these compounds were found to compete for the substrate and sometimes with the ATP site and since EGFR acts as a dimer, we prepared a series of dimeric tyrphostins. These dimeric tyrphostins were built from two BMN units linked by various spacers and designed to fit the dimeric cross-autophosphorylation signal transduction intermediate of the EGFR tyrosine kinases. Structure- activity relationship of these potent dimeric EGF receptor tyrosine kinase inhibitors is reported.
Parallel solution-phase synthesis of targeted tyrphostin libraries with anticancer activity
Hill, Timothy A.,Sakoff, Jennette A.,Robinson, Phillip J.,McCluskey, Adam
, p. 94 - 103 (2005)
The combination of semi-automation, an elegant synthesis, and parallel solution-phase synthesis approaches has allowed the development of five targeted, symmetrical tyrphostin compound libraries. These libraries on average are comprised of 12 compounds. Notwithstanding this, low micromolar potent growth inhibitors against HT29 (colorectal carcinoma) and G401 (renal carcinoma) cell lines were discovered. Additionally, significant SAR data was obtained. We noted that the most potent growth inhibitory activity was consistently observed for those analogues that possessed a 2-chlorophenyl (for 10: GI 50HT29 5.5 ± 0.4 μM, GI50G401 2.6 ± 0.4 μM; for 23: GI50HT29 2.4 ± 0.2 μM, GI50G401 1.9 ± 1 μM; for 34: GI50HT29 8.8 ± 3.1 μM. GI50G401 6.2 ± 2.9 μM; for 46: GI50HT29 5.2 ± 0.9 μM, GI50G401 3.7 ± 0.6 μM; for 57: GI 50HT29 4.6 ± 0.8 μM, GI50G401 2.1 ± 0.2 μM), a 3-chlorophenyl (for 11: GI50HT29 3.8 ± 0.7 μM, GI50G401 1.7 ± 0.7 μM; for 48: GI50HT29 5.9 ± 0.1 μM, GI50G401 3.4 ± 0.6 μM; for 58: GI 50HT29 4.8 ± 0.9 μM, GI50G401 3.4 ± 0.2 μM), or a 3-methoxyphenyl substituent (for 13: GI50HT29 7.4 ± 3.8 μM, GI50G401 2.8 ± 0.5 μM; for 26: GI 50HT29 4.5 ± 0.5 μM, GI50G401 4.9 ± 1 μM; for 37: GI50HT29 3.7 ± 0.2 μM, GI50G401 1.6 ± 0.2 μM; for 49: GI50HT29 3.7 ± 0.4 μM, GI50G401 3.4 ± 0.2 μM; for 60: GI50HT29 4.1 ± 0.6 μM, GI50G401 1.8 ± 0.3 μM). Finally, we noted that increasing the distance between the terminal aromatic rings had only a minimal effect on the 2-, 3-chlorophenyl, and 3-methoxyphenyl analogues, but did have a favourable effect on OH, COOH, and multiply substituted analogues. CSIRO 2005.
Synthesis and reactivity of bis-lactamic compounds
Alexandre, Christian,Melikian, Gaguik,Rouessac, Francis
, p. 1919 - 1925 (1997)
A preparation of bis-lactams is described from α-ketols and bis- cyanamides in the presence of sodium ethoxide at room temperature. One of these compounds leads to an unsaturated derivative by condensation with furfural, or to a saturated analogue via catalytic hydrogenation.
Effective synthesis of new benzo-fused macrocyclic and thiamacrocyclic dilactams and related pyrazolo-fused macrocycles
Ahmed, Ahmed A. M.,Mekky, Ahmed E. M.,Sanad, Sherif M. H.
, p. 286 - 296 (2021/10/19)
In the current study, we examined the synthetic potential of new bis(aldehydes), linked to aliphatic spacers via phenoxy linkage, as versatile building blocks for the synthesis of new macrocyclic dilactams. The target macrocycles were prepared, in 65%–72%
New Bis(dihydropyridine-3,5-dicarbonitrile) Derivatives: Green Synthesis and Cytotoxic Activity Evaluation
Abdelmoniem, Amr M.,Salaheldin, Taher A.,Abdelhamid, Ismail A.,Elwahy, Ahmed H. M.
, p. 2670 - 2677 (2017/09/26)
A synthesis of bis(dihydropyridine-3,5-dicarbonitrile) by a three-component reaction of one equivalent of bis-cyanoacetamides with two equivalents of both arylaldehydes and malononitrile in ethanol-containing piperidine is reported. Bis-cyanopyridones could also be obtained by the condensation of bis-cyanoacetamides with substituted arylidenemalononitriles in the presence of piperidine, chitosan, or montmorillonite as basic catalysts. The cytotoxicity of the synthesized products against the heterogeneous human epithelial colorectal adenocarcinoma cell line (Caco-2) was assessed by WST-1 assay with concentration dependent cellular growth inhibitory effect especially for compounds 5l, 5h, and 5d. The dose response curves indicate that IC50 were 87?±?3.11?μg/mL, 104?±?4.78?μg/mL, and 108?±?5.12?μg/mL, respectively.
Design and synthesis of 2-pyridone based flexible dimers and their conformational study through X-ray diffraction and density functional theory: Perspective of cyclooxygenase-2 inhibition
Rai, Sunil K.,Khanam, Shaziya,Khanna, Ranjana S.,Tewari, Ashish K.
, p. 1430 - 1439 (2015/05/20)
This paper describes the results of X-ray crystallography of 4-methyl-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile (1) and its propylene bridged dimers 2 and 3. Influence of inter- and intramolecular interactions on the conformation of propylene link
Bis-(cyanoacetamide)alkanes in heterocyclic synthesis: Synthesis of bis-heteryl(carboxymido)alkanes and bis-(heteryl)alkanes of thiophene, pyrrole, thiazole and pyrimidinone series
Elneairy, Mohamed A.A.,Mekky, Ahmed E.M.,Ahmed, Ahmed A.M.
experimental part, p. 373 - 383 (2012/08/28)
Bis-N-substituted cyanoacetamides 3a and b reacted with active methylene-containing compounds 2a-c and elemental sulfur to give bis-thiophene 4a and b and bis-pyrrole 6a and b derivatives. Compounds 4a and b reacted with ethyl cyanoacetate 2a to afford bis-thienopyrimidine derivatives 5a and b; on the other hand, 6a and b reacted with cyanothioacetamide 2c to give the corresponding bis-thioxopyrrolopyrimidine derivatives 7a and b. Compounds 7a and b reacted with methyl iodide to give the corresponding bis-2-S- methylpyrrolopyrimidine derivatives 8a and b, which could be, in turn, cyclized into the bispyrazolopyrrolopyrimidine derivatives 9a and b by refluxing with hydrazine hydrate. On the other hand, 7a and b reacted with ethyl chloroacetate to yield the corresponding bis-thienopyrrolopyrimidine derivatives 10a and b. Finally, compounds 3a and b reacted with phenylisothiocyanate and elemental sulfur to give the corresponding bis-2-thioxoaminothizole derivatives 11a and b.
Efficient synthesis of new butenolides by subsequent reactions: Application for the synthesis of original iminolactones, bis-iminolactones and bis-lactones
Cheikh, Nawel,Bar, Nathalie,Choukchou-Braham, Nourredine,Mostefa-Kara, Bachir,Lohier, Jean-Franois,Sopkova, Jana,Villemin, Didier
experimental part, p. 1540 - 1551 (2011/04/15)
We have developed the synthesis of twenty four new iminolactones, bis-iminolactones and bis-lactones by subsequent esterification-condensation or addition-condensation reactions according to two strategies from α-hydroxyketones. The X-ray diffraction data of a bis-iminolactone is described and present an interesting helical column packing.
Small molecule inhibitors of dynamin I GTPase activity: Development of dimeric tyrphostins
Hill, Timothy,Odell, Luke R.,Edwards, Jennifer K.,Graham, Mark E.,McGeachie, Andrew B.,Rusak, Jenny,Quan, Annie,Abagyan, Ruben,Scott, Janet L.,Robinson, Phillip J.,McCluskey, Adam
, p. 7781 - 7788 (2007/10/03)
Dynamin I is a GTPase enzyme required for endocytosis and is an excellent target for the design of potential endocytosis inhibitors. Screening of a library of tyrphostins, in our laboratory, against the GTPase activity of dynamin I gave rise to a ìèpotent lead, 2-cyano-3-(3,4- dihydroxyphenyl)thioacrylamide (1, IC50 70 μM). Our initial investigations suggested that only the dimeric form of 1 displayed dynamin I GTPase inhibitory activity. Subsequent synthetic iterations were based on dimeric analogues and afforded a number of small molecules, low μM potent, inhibitors of dynamin I GTPase, in particular, symmetrical analogues with a minimum of two free phenolic -OHs: catechol-acrylamide (9) (IC50 = 5.1 ± 0.6 μM), its 3,4,5-trihydroxy congener (10) (IC50 = 1.7 ± 0.2 μM), and the corresponding 3-methyl ether (11) (IC 50 = 9 ± 3 μM). Increasing the length of the central alkyl spacer from ethyl to propyl (22-24) afforded essentially identical activity with IC50's of 1.7 ± 0.2, 1.7 ± 0.2, and 5 ± 1 μM, respectively. No decrease in activity was noted until the introduction of a hexyl spacer. Our studies highlight the requirement for two free amido NHs with neither the mono-N-methyl (86) nor the bis-N-methyl (87) analogues inhibiting dynamin I GTPase. A similar effect was noted for the removal of the nitrile moieties. However, modest potency was observed with the corresponding ester analogues of 9-11: ethyl ester (90), propyl ester (91), and butyl ester (92), with IC50's of 42 ± 3, 38 ± 2, and 61 ± 2 μM, respectively. Our studies reveal the most potent and promising dynamin I GTPase inhibitor in this series as (22), which is also known as BisT.
