77008-48-1Relevant academic research and scientific papers
Introducing of potent cytotoxic novel 2-(aroylamino)cinnamamide derivatives against colon cancer mediated by dual apoptotic signal activation and oxidative stress
Abdel-Bakky, Mohamed S.,Abdelghany, Tamer M.,Ahmed, Hany E. A.,Ahmed, Mostafa H.,Boothello, Rio,El-Araby, Moustafa E.,Elhaggar, Radwan S.,Malebari, Azizah M.,Omar, Abdelsattar M.,Patel, Bhaumik B,Safo, Martin K.
, (2020/06/01)
Curcumin and trans-cinnamaldehyde are acrolein-based Michael acceptor compounds that are commonly found in domestic condiments, and known to cause cancer cell death via redox mechanisms. Based on the structural features of these compounds we designed and synthesized several 2-cinnamamido-N-substituted-cinnamamide (bis-cinnamamide) compounds. One of the derivatives, (Z)-2-[(E)-cinnamamido]-3-phenyl-N-propylacrylamide 8 showed a moderate antiproliferative potency (HCT-116 cell line inhibition of 32.0 μM), no inhibition of normal cell lines C-166, and proven cellular activities leading to apoptosis. SAR studies led to more than 10-fold increase in activity. Our most promising compound, [(Z)-3-(1H-indol-3-yl)-N-propyl-2-[(E)-3-(thien-2-yl)propenamido)propenamide] 45 killed colon cancer cells at IC50 = 0.89 μM (Caco-2), 2.85 μM (HCT-116) and 1.65 μM (HT-29), while exhibiting much weaker potency on C-166 and BHK normal cell lines (IC50 = 71 μM and 77.6 μM, respectively). Cellular studies towards identifying the compounds mechanism of cytotoxic activities revealed that apoptotic induction occurs in part as a result of oxidative stress. Importantly, the compounds showed inhibition of cancer stem cells that are critical for maintaining the potential for self-renewal and stemness. The results presented here show discovery of covalently acting Michael addition compounds that potently kill cancer cells by a defined mechanism, with prominent selectivity profile over non-cancerous cell lines.
Acid-aided reactions of 3-acylamino-β-lactams: Some observations
Sanjayan, Gangadhar J.,Mukerjee, Arya K.
, p. 76 - 78 (2007/10/02)
3-Benzoylamino-1,4-diphenylazetidin-2-one (1a) gives 2-benzoylaminocinnamanilide (3a) and 4-benzylidene-1,2-diphenylimidazolin-5-one (4a) when heated in gl. acetic acid containing conc.H2SO4. 3-Acetylaminoazetidin-2-one (1b) forms tar under similar conditions, but in the presence of benzaldehyde it affords 2-cinnamoylaminocinnamanilide (3c) and 4-benzylidene-2-styryl-2-imidazolin-5-one (4c). 3-(2-Benzoylaminocinnamoylamino)-1,4-diphenylazetidin-2-one (1c), on the other hand furnishes 4-benzylidene-2-phenyl-2-oxazolin-5-one (2a) and 3-amino-1,4-diphenylazetidin-2-one (14).Mechanisms are given.
Isothiocyanate-Mediated Condensation of N-Acyl-α-amino Acids with Aromatic Aldehydes: One-Pot Synthesis of 1,2-Disubstituted 4-Arylmethylene-2-imidazolin-5-ones
Ashare, Ram,Mukerjee, Arya K.
, p. 762 - 764 (2007/10/02)
N-Acetyl/benzoyl-amino acids (1c/1b, d) when heated with isothiocyanates (2) in the presence of suitable aromatic aldehydes (3) with pyridine as a catalyst, afford 1, 2-disubstituted 4-arylmethylene-2-imidazolin-5-ones (6).However, N-benzyloxycarbonylaminoacetic acid (1a) gives the corresponding anilide (11a).Mechanisms of these reactions are discussed.
Condensation of 4-Benzylidene-2-methyloxazolin-5-one with Schiff Bases: Formation of 1-Aryl-4-benzylidene-2-styrylimidazolin-5-ones
Reddy, M. Satyanarayana,Hanumanthu, P.,Ratnam, C. V.
, p. 646 - 648 (2007/10/02)
Condensation of 4-benzylidene-2-methyloxazolin-5-one (II) with schiff bases (I) in acetic acid results in 1-aryl-4-benzylidene-2-styrylimidazolin-5-ones (III) and α-acetamidocinnamanilides (IV), characterised by spectral, analytical and chemical methods.
