79128-71-5Relevant academic research and scientific papers
Design, structure-activity relationship study and biological evaluation of the thieno[3,2-c]isoquinoline scaffold as a potential anti-cancer agent
Liu, Jiang Tian,Jaunky, Dilan B.,Larocque, Kevin,Chen, Fei,Mckibbon, Keegan,Sirouspour, Mehdi,Taylor, Sarah,Shafeii, Alexandre,Campbell, Donald,Braga, Helena,Piekny, Alisa,Forgione, Pat
supporting information, (2021/10/04)
Several derivatives of a series that share a thienoisoquinoline scaffold have demonstrated potent activity against cancer cell lines A549, HeLa, HCT-116, and MDA-MB-231 in the submicromolar concentration range. Structure-activity relationship (SAR) studies on a range of derivatives aided in identifying key pharmacophores in the lead compound. A series of compounds have been identified as the most promising with submicromolar IC50 values against a lung cancer cell line (A549). Microscopy studies of cancer cells treated with the lead compound revealed that it causes mitotic arrest and disrupts microtubules. Further evaluation via an in vitro microtubule polymerization assay and competition studies indicate that the lead compound binds to tubulin via the colchicine site.
Synthesis and SAR studies of novel 1,2,4-oxadiazole-sulfonamide based compounds as potential anticancer agents for colorectal cancer therapy
Abid, Mohammad,Alajmi, Mohamed F.,Garrison, Jered,Hasan, Phool,Hussain, Afzal,Imtaiyaz Hassan, Md,Khan, Parvez,King, Hannah M.,Queen, Aarfa,Rana, Sandeep,Rizvi, M. Moshahid Alam,Shamsi, Farheen,Zahid, Muhammad,Zeya, Bushra
, (2020/03/23)
A diverse series of 1,2,4-oxadiazoles based substituted compounds were designed, synthesized and evaluated as anticancer agents targeting carbonic anhydrase IX (CAIX). Initial structure-activity analysis suggested that the thiazole/thiophene-sulfonamide conjugates of 1,2,4-oxadiazoles exhibited potent anticancer activities with low μM potencies. Compound OX12 exhibited antiproliferative activity (IC50 = 11.1 μM) along with appreciable inhibition potential for tumor-associated CAIX (IC50 = 4.23 μM) isoform. Therefore, OX12 was structurally optimized and its SAR oriented derivatives (OX17-27) were synthesized and evaluated. This iteration resulted in compound OX27 with an almost two-fold increase in antiproliferative effect (IC50 = 6.0 μM) comparable to the clinical drug doxorubicin and significantly higher potency against CAIX (IC50 = 0.74 μM). Additionally, OX27 treatment decreases the expression of CAIX, induces apoptosis and ROS production, inhibited colony formation and migration of colon cancer cells. Our studies provide preclinical rational for the further optimization of identified OX27 as a suitable lead for the possible treatment of CRC.
Synthesis of 2,5-diaryl-substituted thiophenes as helical mimetics: Towards the modulation of islet amyloid polypeptide (IAPP) amyloid fibril formation and cytotoxicity
Hassanpour, Avid,Dea Carufel, Carole Anne,Bourgault, Steve,Forgione, Pat
supporting information, p. 2522 - 2528 (2014/03/21)
A range of 2,5-diarylated thiophenes were synthesised as small molecule mimetics of the α-helix to modulate the amyloidogenesis and cytotoxic effect of islet amyloid polypeptide (IAPP). 3-Substituted thiophene-2-carboxylic acids were used as key intermediates and functionalised by palladium decarboxylative cross-coupling and direct C=H activation successively with overall yields ranging from 23 to 95 %. The effect of the ligands on IAPP amyloid fibril formation was evaluated with the thioflavina T (ThT) fluorescence-based assay. Furthermore, the capacity of these compounds to inhibit the cytotoxic effect of IAPP was assessed using β-pancreatic cells. A twist manipulated: A range of 2,5-diarylated thiophenes was synthesised as small molecule mimetics of the α-helix to modulate the amyloidogenesis and cytotoxic effect of islet amyloid polypeptide (IAPP; see scheme). The effect of the ligands on IAPP amyloid fibril formation was evaluated. Furthermore, the capacity of these compounds to inhibit the cytotoxic effect of IAPP was assessed using β-pancreatic cells. Copyright
DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS
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Paragraph 0293; 0294, (2014/01/07)
Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols according to formula (I) are useful as inhibitors of the phosphodiesterase 4 (PDE4) enzyme.
DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS
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Page/Page column 68, (2014/01/08)
The invention relates to inhibitors of the phosphodiesterase 4 (PDE4) enzyme. More particularly, the invention relates to compounds that are derivatives of 1 -phenyl-2-pyridinyl alkyl alcohols, methods of preparing such compounds, compositions containing them and therapeutic use thereof.
Microwave-induced rapid access to aromatic and heteroaromatic sulfonamides under solvent-free conditions without using external base
Sharma, Ashwani Kumar,Das, Saibal Kumar
, p. 3807 - 3819 (2007/10/03)
Microwave-induced syntheses of sulfonamides, without using base under solvent-free conditions, have been developed. The process finds its utility because of its simple operational procedure and high yields. Moreover, the process is fast and accommodative to different substituents on aromatic as well as heteroaromatic rings rendering sulfonamides (28 examples).
Novel heterocycles. Synthesis of 2,3-dihydro-6-methyl-2-phenyl-4H,6H- pyranol[3,2-c][2,1]benzothiazin-4-one 5,5-dioxide and related compounds
Coppo,Fawzi
, p. 983 - 987 (2007/10/03)
The reaction of 2-chloro-4-(methylsulfonyl)benzoyl chloride (5) with 1- methyl-1H-2,1-benzothiazin-4-(3H)-one 2,2-dioxide (4) gave the O-benzoyl compound, 1-methyl-2,2-dioxido-1H-2,1-benzothiazin-4-yl 2-chloro-4- (methylsulfonyl)benzoate (6), which rearra
