- The total syntheses of JBIR-94 and two synthetic analogs and their cytotoxicities against A549 (CCL-185) human small lung cancer cells
-
We here disclose the total syntheses of the natural polyphenol JBIR-94 and two nonnatural analogs, whose structures are of interest for their bioactivity potential as radical scavengers. Although we initially attempted this by dually acylating both of putrecine's amine nitrogens in a single pot, our endeavors with this method (which has been successfully reported by other groups) proved ineffectual. We accordingly opted for the lengthier approach of acylating each amine individually, which gratuitously prevailed and also aligns with separate literature precedent. Moreover, we here share our analysis of these target compounds’ cytotoxicities and IC50 values against A549 (CCL-185) human small lung cancer cells.
- Mangum, Cathy L.,Munford, Mica B.,Sam, Alyssa B.,Young, Sandra K.,Beales, Jeremy T.,Subedi, Yagya Prasad,Mangum, Chad D.,Allen, Tanner J.,Liddell, Miranda S.,Merrell, Andrew I.,Saavedra, Diana I.,Williams, Becky L.,Evans, Nicole,Beales, Joseph L.,Christiansen, Michael A.
-
supporting information
(2019/11/29)
-
- Modular synthesis and biological investigation of 5-hydroxymethyl dibenzyl butyrolactones and related lignans
-
Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to give rise to 5-hydroxymethyl derivatives of these lignans. The biological activities of these analogues were assessed, with derivatives showing an excellent cytotoxic profile which resulted in programmed cell death of Jurkat T-leukemia cells with less than 2% of the incubated cells entering a necrotic cell death pathway.
- Davidson, Samuel J.,Pilkington, Lisa I.,Dempsey-Hibbert, Nina C.,El-Mohtadi, Mohamed,Tang, Shiying,Wainwright, Thomas,Whitehead, Kathryn A.,Barker, David
-
-
- Asymmetric synthesis of O-methylneferine
-
Diastereoselective Pictet-Spengler reaction of 2-arylethylamine bearing an N-(R)-1-(1-naphthyl)ethylcarbamoyl group with arylacetaldehyde gave 1-benzyltetrahydroisoquinoline in good yield with moderate diastereoselectivity. The reaction was applied to asymmetric synthesis of O-methyl derivative of neferine, an alkaloid of the lotus embryo, Nelumbo nucifera Gaertner.
- Nishimura, Katsumi,Horii, Shinji,Tanahashi, Takao
-
p. 865 - 876
(2019/04/26)
-
- An access to chiral β-benzyl-γ-butyrolactones and its application to the synthesis of enantiopure (+)-secoisolariciresinol, (-)-secoisolariciresinol, and (-)-enterolactone
-
Both enantiomers of secoisolariciresinol and enantiopure (-)-enterolactone were synthesized through a highly stereoselective convergent synthesis. An Evans diastereoselective alkylation followed by a substrate-induced diastereoselective -alkylation of the newly formed optically active β-benzyl-γ- butyrolactone gave the β-β′ linkage of the target skeleton. The (S,S)- and (R,R)-enantiomers of secoisolariciresinol and (-)-enterolactone were obtained in 12-14% (11 steps) and 20% (7 steps) overall yield, respectively. Georg Thieme Verlag Stuttgart New York.
- Allais, Florent,Pla, Thomas J. L.,Ducrot, Paul-Henri
-
experimental part
p. 1456 - 1464
(2011/06/17)
-
- AMIDES AND METHOD FOR PLANT DISEASE CONTROL WITH THE SAME
-
N-(α-cyanobenzyl)amide compounds represented by the formula (1): wherein R1 represents a hydrogen atom; a halogen atom; a C1-C6 alkyl group optionally substituted with a halogen atom or the like; or the like, R2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group or the like, R3 represents a hydrogen atom or the like, R4 represents a C1-C4 alkyl group, a C3-C4 alkenyl group or the like, R5 represents a C1-C4 alkyl group, a C3-C4 alkenyl group, or the like, R6 represents a hydrogen atom or the like, R7 represents a hydrogen atom or the like, R8 represents a hydrogen atom or the like, R9 represents a hydrogen atom or the like, R10 represents a hydrogen atom or the like, R11 represents a hydrogen atom or the like, and R12 represents a hydrogen atom or the like, have excellent control activities against plant diseases.
- -
-
Page/Page column 83
(2010/11/08)
-
- INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME
-
Compounds of formula (I) are hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors, and are useful in therapeutic and prophylactic treatment of persons infected with hepatitis C virus.
- -
-
Page/Page column 45
(2010/02/07)
-
- 8,9-Methylenedioxybenzo[i]phenanthridines: Topoisomerase I-targeting activity and cytotoxicity
-
Substituted benzo[i]phenanthridines that have incorporated within their structure an 8,9-methylenedioxy group can exhibit topoisomerase I-targeting activity. Structure-activity studies were performed to examine the influence of saturation at the 11,12-positions of several substituted 8,9-methylenedioxybenzo[i]phenanthridines. The activities of these dihydro analogues were compared to those of their unsaturated analogues. In addition, the influence of varying substituents at the 2- and 3-positions within the A-ring of these 8,9-methylenedioxybenzo[i]phenanthridines on their relative potency as topoisomerase I-targeting agents and cell proliferation as determined using the MTT assay was investigated. 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and its 11,12-dihydro derivative were among the more potent analogues evaluated with regard to topoisomerase I-targeting activity and cytotoxicity.
- Li, Dajie,Zhao, Baoping,Sim, Sai-Peng,Li, Tsai-Kun,Liu, Angela,Liu, Leroy F.,LaVoie, Edmond J.
-
p. 3795 - 3805
(2007/10/03)
-
- Total Synthesis of (+/-)-Wikstromol
-
The antineoplastic prototype lignan natural product wikstromol was synthesized in racemic form by a straightforward sequence involving, as its key transformations,oxidative coupling of a carboxylic acid dianion,generation and stereoselective oxidation of a potassium enolate,and a deprotection step.The overall yield for nine steps is 29percent.Depending on the choice of oxidants for the enolate,considerable modification in the ratio of stereoisomeric products is possible.
- Belletire,John L.,Fry,Douglas F.
-
p. 4724 - 4729
(2007/10/02)
-
- Synthesis of Dihydrocurcumin
-
Dihydrocurcumin is synthesised by C-acylation of 4-O-benzylvanillylideneaceton (3b) with 4-O-benzyldihydroferulic acid chloride (2b) in the presence of NaH-THF.
- Krishnamurty, H. G.,Ghosh, Sanjukta
-
p. 411 - 412
(2007/10/02)
-
- Structure and Synthesis of New Phenolic Amides from Piper nigrum L.
-
New phenolic amides, N-trans-feruloyl piperidine (4a), N-5-(4-hydroxy-3-methoxyphenyl)-2E,4E-pentadienoyl piperidine (5a) and N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoyl piperidine (6a) were isolated from the fruit of white pepper (Piper nigrum L.).The f
- Inatani, Reiko,Nakatani, Nobuji,Fuwa, Hidetsugu
-
p. 667 - 674
(2007/10/02)
-