101-97-3Relevant articles and documents
Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates
Scheidt, Karl A.,Zhu, Joshua L.
, (2021)
Despite recent advancements in the selective generation and coupling of organic radical species, the alkoxycarbonyl radical remains underexplored relative to other carbon-containing radical species. Drawing inspiration from new strategies for generating acyl radical equivalents utilizing dual N-heterocyclic carbene catalysis and photocatalysis, we have prepared dimethylimidazolium esters that can function as an alkoxycarbonyl radical surrogate under photocatalytic conditions. We demonstrate the synthetic utility of these azolium-based partners through the preparation of esters arising from the coupling of this radical surrogate with an oxidatively generated alkyl radical.
Chemoenzymatic synthesis and antileukemic activity of novel C9- and C14-functionalized parthenolide analogs
Tyagi, Vikas,Alwaseem, Hanan,O'Dwyer, Kristen M.,Ponder, Jessica,Li, Qi Ying,Jordan, Craig T.,Fasan, Rudi
, p. 3876 - 3886 (2016)
Parthenolide is a naturally occurring terpene with promising anticancer properties, particularly in the context of acute myeloid leukemia (AML). Optimization of this natural product has been challenged by limited opportunities for the late-stage functionalization of this molecule without affecting the pharmacologically important α-methylene-γ-lactone moiety. Here, we report the further development and application of a chemoenzymatic strategy to afford a series of new analogs of parthenolide functionalized at the aliphatic positions C9 and C14. Several of these compounds were determined to be able to kill leukemia cells and patient-derived primary AML specimens with improved activity compared to parthenolide, exhibiting LC50values in the low micromolar range. These studies demonstrate that different O–H functionalization chemistries can be applied to elaborate the parthenolide scaffold and that modifications at the C9 or C14 position can effectively enhance the antileukemic properties of this natural product. The C9-functionalized analogs 22a and 25b were identified as the most interesting compounds in terms of antileukemic potency and selectivity toward AML versus healthy blood cells.
TRANSITION METAL COMPLEX CATALYZED CARBONYLATION OF ORGANIC HALIDES IN THE PRESENCE OF MOLECULAR SIEVES INSTEAD OF BASE
Urata, Hisao,Hu, Nan-Xing,Maekawa, Hisayuki,Fuchikami, Takamasa
, p. 4733 - 4736 (1991)
In the presence of molecular sieves under base free conditions organic halides are successfully carbonylated under carbon monoxide pressure with water or alcohols catalyzed by Co or Pd complex to generate the corresponding carboxylic acids or esters, respectively, in good yields.
Trimethylamine N-oxide: A novel reagent for the promotion of the retro- aldol reaction of R106-1 (LY295337)
Rodriguez,Zweifel
, p. 4301 - 4304 (1996)
The retro-aldol reaction of R106-1 (LY295337), 1 using trimethylamine N- oxide (TNO) facilitates the removal of the tertiary hydroxy group generating R106-sarcosine, 2 a key synthetic intermediate. The reagent is highly reproducible and provides high yields with no major side products. A side by side comparison of TNO vs. traditional bases is described.
S,S'-Bis(1-phenyl-1H-tetrazol-5-yl) Dithiocarbonate: A New Esterification Reagent
Takeda, Kazuyoshi,Tsuboyama, Kanoko,Takayanagi, Hiroaki,Ogura, Haruo
, p. 560 - 562 (1987)
S,S'-Bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate is a useful reagent for the esterification of carboxylic acids with alcohols, including lactonization.The reagent is conveniently prepared in good yield from 1-phenyl-5-thioxo-4,5-dihydro-1H-tetrazole and trichloromethyl chloroformate (trichloromethyl carbonochloridate) in ethyl acetate in the presence of triethylamine.Its structure was confirmed by (13)C-NMR spectrometry and single-crystal X-ray analysis.
Radical aromatic substitution via atom-transfer addition
Byers, Jeffrey H.,Campbell, John E.,Knapp, Faith H.,Thissell, Jameson G.
, p. 2677 - 2680 (1999)
New methodology for radical aromatic substitution has been developed involving the addition of electron-deficient radicals to unprotected pyrroles and indole. This non-oxidative process is presumed to be occurring via atom- transfer addition of suitable organoiodides and bromides with subsequent non- radical elimination of HI or HBr, respectively. The process also occurs under stannane-free conditions.
Structure activity relationship of organic alcohol and esters for antidepressant-like activity
Perveen, Shahnaz,Yasmeen, Arfa,Khan, Muhammad Aitmaud,Dar, Ahsana,Jafri, Rehana,Ahmed, Amir
, p. 14 - 17 (2010)
The synthesized compounds 1-7 were evaluated for their antidepressant activity, among which 2-phenylethyl alcohol 1 and isoamyl phenylacetate 3 showed 43 % and 37 % reduction in immobility time in mice using forced swim test, thereby, displaying antidepressant-like activity. Compound 1 and 3 were equipotent and both these compounds were 2x effective than the standard drug phenelzine. Considering other esters it appears that a decrease in alkyl chain length or addition of either NO2 or OH groups to the phenyl ring caused a marked decline in the antidepressant-like activity.
Pd-catalyzed synthesis of arylacetic acid derivatives from boronic acids
Goossen
, p. 669 - 670 (2001)
A palladium(0)-catalyzed cross-coupling reaction between arylboronic acids or esters and α-bromoacetic acid derivatives is described which allows the synthesis of various functionalized arylacetic acid derivatives under mild conditions.
Metal-free hydroalkoxylation of ynesulfonamides with esters
Gao, Erhui,Peng, Cheng,Zhang, Jingyi,Wang, Xiao-Na,Chang, Junbiao
, p. 2182 - 2185 (2021)
An efficient metal-free hydroalkoxylation reaction of ynesulfonamides with esters under mild conditions is described. Under the catalysis of TMSOTf, various ynesulfonamides are transformed into the corresponding alkoxy-substituted enamides in high yields
Synthesis, Structural Analysis, and Screening of Some Novel 5-Substituted Aryl/Aralkyl-1,3,4-Oxadiazol-2-Yl 4-(Morpholin-4-Ylsulfonyl)Benzyl Sulfides As Potential Antibacterial Agents
Aziz-Ur-Rehman,Gul, Samreen,Abbasi, Muhammad Athar,Nafeesa, Khadija,Akhtar, Muhammad Nadeem,Ahmad, Irshad,Afzal, Saira
, p. 1045 - 1055 (2015)
A series of new 5-substituted aryl/aralkyl-1,3,4-oxadiazol-2-yl 4-(morpholin-4-ylsulfonyl)benzyl sulfides 6a-k were synthesized by converting multifarious aryl/aralkyl organic acids 1a-k successively into corresponding esters 2a-k, hydrazides 3a-k, and 5-substituted aryl/aralkyl-1,3,4-oxadiazole-2-thiols 4a-k. Finally, the target compounds, 6a-k were prepared by stirring 5-substituted-1,3,4-oxadiazole-2-thiols with 4-(4-(bromomethyl)phenylsulfonyl) morpholine (5) in the presence of N,N-dimethylformamide (DMF) and sodium hydride (NaH). The structures of the newly synthesized compounds were elucidated by spectroscopic techniques. In addition, the antibacterial activity of all the synthesized compounds was investigated in vitro against Gram-positive and Gram-negative bacteria by using ciprofloxacin as reference standard drug and the results showed that some of the tested compounds possessed good antibacterial activity.
