57093-55-7Relevant articles and documents
Distal γ-C(sp3)?H Olefination of Ketone Derivatives and Free Carboxylic Acids
Fan, Zhoulong,Park, Han Seul,Yu, Jin-Quan,Zhu, Ru-Yi
supporting information, p. 12853 - 12859 (2020/06/10)
Reported herein is the distal γ-C(sp3)?H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino-acid directing group and using the ligand combination of a mono-N-protected amino acid (MPAA) and an electron-deficient 2-pyridone were critical for the γ-C(sp3)?H olefination of ketone substrates. In addition, MPAAs enabled the γ-C(sp3)?H olefination of free carboxylic acids to form diverse six-membered lactones. Besides alkyl carboxylic acids, benzylic C(sp3)?H bonds also could be functionalized to form 3,4-dihydroisocoumarin structures in a single step from 2-methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the γ-C(sp3)?H olefinated products.
Carbon chain shape selectivity by the mouse olfactory receptor OR-I7
Liu, Min Ting,Ho, Jianghai,Liu, Jason Karl,Purakait, Radhanath,Morzan, Uriel N.,Ahmed, Lucky,Batista, Victor S.,Matsunami, Hiroaki,Ryan, Kevin
, p. 2541 - 2548 (2018/04/12)
The rodent OR-I7 is an olfactory receptor exemplar activated by aliphatic aldehydes such as octanal. Normal alkanals shorter than heptanal bind OR-I7 without activating it and hence function as antagonists in vitro. We report a series of aldehydes designed to probe the structural requirements for aliphatic ligand chains too short to meet the minimum approximate 6.9 ? length requirement for receptor activation. Experiments using recombinant mouse OR-I7 expressed in heterologous cells show that in the context of short aldehyde antagonists, OR-I7 prefers binding aliphatic chains without branches, though a single methyl on carbon-3 is permitted. The receptor can accommodate a surprisingly large number of carbons (e.g. ten in adamantyl) as long as the carbons are part of a conformationally constrained ring system. A rhodopsin-based homology model of mouse OR-I7 docked with the new antagonists suggests that small alkyl branches on the alkyl chain sterically interfere with the hydrophobic residues lining the binding site, but branch carbons can be accommodated when tied back into a compact ring system like the adamantyl and bicyclo[2.2.2]octyl systems.
HEPATITIS C INHIBITOR DIPEPTIDE ANALOGS
-
Page/Page column 83, (2008/06/13)
The present invention relates to compounds of formula (I): wherein R1, R2, R4, n and m are as defined herein and R3 is selected from: (i) -C(O)OR31 wherein R31 is (C1-6)alkyl or aryl, wherein the (C1-6)alkyl is optionally substituted with one to three halogen substituents; (ii) -C(O)NR32R33, wherein R32 and R33 are each independently selected form H, (C1-6)alkyl, and Het; (iii) -SOvR34, wherein v is 1 or 2 and R34 is selected from: (C1-6)alkyl, aryl, Het, and NR32R33 wherein R32 and R33 are as defined above; and (iv) -CO(O)-R35, wherein R35 is selected from (C1-8)alkyl, (C3-7)cycloalkyl-(C1-4)alkyl, aryl, aryl-(C1-6)alkyl, Het and Het-(C1-6)alkyl, each of which are optionally substituted with one or more substituents each independently selected from halo, (C1-6)alkyl, (C3-7)cycloalkyl, aryl, Het, hydroxyl, -O-(C1-6)alkyl, -S-(C1-6)alkyl, -SO-(C1-6)alkyl, -SO2-(C1-6)alkyl, -O-aryl, -S-aryl, -SO-aryl and -SO2-aryl, wherein the aryl portion of the -O-aryl, -S-aryl, -SO-aryl and -SO2-aryl are each optionally substituted with one to five halo substituents. The present invention further relates to pharmaceutical compositions containing the compounds of formula (I) and methods for using these analogs in the treatment of HCV infection.
Synthesis and Properties of Some tert-Alkylmalonic Acid Derivatives
Holmberg, Carl
, p. 748 - 760 (2007/10/02)
1,4-Addition of Grignard reagents to the alkylidenemalonic acid derivatives 1-8 affords the tert-alkyl malonic derivatives 9-18.The esters 9-17 give the acids 19-26 and from these the corresponding chlorides 27-34 are obtained.Bromination yields the bromo acids 35-36, the brominated acyl bromide 43, the bromonitrile 44, and the bromoacyl chlorides 37-42.The trimethylsilyl esters 50-52, the bis(2-bromoethyl) esters 53-54, the ethyl ester 14, and the tert-butyl ester 16 are brominated via the corresponding ester enolates giving the bromo esters 45-46 in pure form. - The dealkylation of malonic esters with chlorotrimethylsilane/sodium iodide has been carried out.
