ChemInform Abstract: PALLADIUM-CATALYZED REACTION OF ALLYL ACETATE, ALLYL BENZOATE, ALLYL CHLORIDE, ALLYL BROMIDE, DIALLYL ETHER, AND ALLYL ALCOHOL WITH BENZENE

1985 ◽  
Vol 16 (36) ◽  
Author(s):  
M. YOSHIDOMI ◽  
Y. FUJIWARA ◽  
H. TANIGUCHI
Keyword(s):  
Allyl Alcohol ◽  
Allyl Bromide ◽  
Allyl Chloride ◽  
Allyl Acetate ◽  
Palladium Catalyzed ◽  
Diallyl Ether

Synthesis of a novel brominated vinylic fatty acid with antileishmanial activity that effectively inhibits the Leishmania topoisomerase IB enzyme mediated by halogen bond formation

2019 ◽  
Vol 91 (8) ◽  
pp. 1405-1416
Author(s):  
Néstor M. Carballeira ◽  
Denisse Alequín ◽  
Leilani M. Lotti Diaz ◽  
Victorio Jauregui Matos ◽  
Leonardo L. G. Ferreira ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Allyl Bromide ◽  
Halogen Bond ◽  
Allyl Chloride ◽  
Phosphate Binding ◽  
Dna Topoisomerase ◽  
Synthetic Compounds ◽  
Topoisomerase Ib ◽  
Independent Mechanism ◽  
Palladium Catalyzed

AbstractMany marine derived fatty acids, mainly from sponges, possess vinylic halogenated moieties (bromine or iodine) but their assessment as antileishmanial candidates remains elusive. In this work, we undertook the first total synthesis of a novel series of 2-allyl-3-halo-2-nonadecenoic acids, which preferentially inhibit theLeishmaniaDNA topoisomerase IB enzyme (LTopIB) over the human topoisomerase IB enzyme (hTopIB). The synthesis of 2-allyl-3-bromo-2E-nonadecenoic acid (1a) and 2-allyl-3-chloro-2E-nonadecenoic acid (2a) was achieved through a palladium catalyzed haloallylation of 2-nonadecynoic acid (2-NDA) using either allyl bromide or allyl chloride in the presence of PdCl2(PhCN)2in 57–83 % overall yields. Among the new halogenated synthetic compounds,1awas the most inhibitory ofLTopIB with an EC50 = 7 μM, while the shorter chain analogs 2-allyl-3-bromo-2E-dodecenoic acid (1b) and 2-allyl-3-chloro-2E-dodecenoic acid (2b), synthesized from 2-dodecynoic acid, were not inhibitory ofLTopIB (EC50 > 100 μM) resulting in the overall order of inhibition1a > 2-NDA > 2a > > 1b ≅ 2b. The acids1aand2ainhibitLTopIB by a Gimatecan-independent mechanism. The enhancedLTopIB inhibition of1awas computationally rationalized in terms of a halogen bond between the bromine in1aand a DNA phosphate (binding energy = − 4.85 kcal/mol). Acid1aalso displayed preferential cytotoxicity towardsLeishmania infantumamastigotes (EC50 = 2.5 μM) overL. infantumpromastigotes (EC50 > 25 μM).

scholarly journals Palladium-Catalyzed Isomerization-Coupling Reactions of Allyl Chloride with Amines to Generate Functionalized Phosphorus Derivatives

Catalysts ◽  
2018 ◽  
Vol 8 (5) ◽  
pp. 194
Author(s):  
Jing-Hong Wen ◽  
Qiang Li ◽  
Shao-Zhen Nie ◽  
Jing-Jing Ye ◽  
Qing Xu ◽  
...  
Keyword(s):  
Allyl Chloride ◽  
Coupling Reactions ◽  
Palladium Catalyzed

Radical polymerization of allyl alcohol and allyl acetate

2007 ◽  
Vol 18 (12) ◽  
pp. 953-958 ◽  
Author(s):  
Kokoro Iio ◽  
Kentaro Kobayashi ◽  
Mutsuo Matsunaga
Keyword(s):  
Radical Polymerization ◽  
Allyl Alcohol ◽  
Allyl Acetate

Palladium-Catalyzed Consecutive One-Pot Reaction of Acetylenes with Allyl Bromide and Organotin Compounds

1993 ◽  
Vol 66 (10) ◽  
pp. 3058-3061 ◽  
Author(s):  
Masanori Kosugi ◽  
Takashi Sakaya ◽  
Shinji Ogawa ◽  
Toshihiko Migita
Keyword(s):  
Allyl Bromide ◽  
Organotin Compounds ◽  
One Pot ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Coupling of Haloalkynes with Allyl Acetate: A Regio- and Stereoselective Synthesis of (Z)-β-Haloenol Acetates.

ChemInform ◽  
2011 ◽  
Vol 42 (49) ◽  
pp. no-no
Author(s):  
Xiaoyi Chen ◽  
Dongxu Chen ◽  
Zenghui Lu ◽  
Lichun Kong ◽  
Gangguo Zhu
Keyword(s):  
Stereoselective Synthesis ◽  
Allyl Acetate ◽  
Palladium Catalyzed
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