- Cross-Coupling Reactions of Aryl Halides with Primary and Secondary Aliphatic Alcohols Catalyzed by an O,N,N-Coordinated Nickel Complex
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A synthesis of alkyl aryl ethers was achieved via the cross-coupling of aryl halides with primary and secondary aliphatic alcohols catalyzed by a bench-stable nickel complex supported by a monoanionic O,N,N-tridentate ligand. This nickel-catalyzed reaction proceeds smoothly in the absence of a phosphine ligand, affording alkyl aryl ethers in moderate to good yields. (Figure presented.).
- Hashimoto, Toru,Shiota, Keisuke,Funatsu, Kei,Yamaguchi, Yoshitaka
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supporting information
p. 1625 - 1630
(2021/01/26)
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- Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction
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A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic diamides serve as the powerful ligands. The tert-butoxide is first demonstrated as a ligand for Cu-catalyzed coupling reaction, leading to alkoxylation of aryl iodides complete at room temperature. Additionally, a number of carbohydrate derivatives are applicable for this coupling reaction, affording the corresponding carbohydrate-aryl ethers in 29-98% yields.
- Chen, Zhixiang,Jiang, Yongwen,Zhang, Li,Guo, Yinlong,Ma, Dawei
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supporting information
p. 3541 - 3549
(2019/02/26)
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- Unprecedented alkylation of carboxylic acids by boron trifluoride etherate
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The alkylation of carboxylic acids by an ethyl moiety of boron trifluoride etherate in the absence of ethyl alcohol from the reaction system is unexpected and novel. Both aromatic and aliphatic carboxylic acids were clearly alkylated affording good yields in short reaction times with the exception of nicotinic acid that necessitated an overnight reaction. It was noted that while ortho-substituted hydroxyl groups of carboxylic acids investigated were not affected by alkylation, those of meta- and para-substituted carboxylic acids were partially etherified. Furthermore, the alkylation reaction was found to be compatible with a range of functional groups such as halogens, amino and nitro groups except for the alkene function of undecylenic acid that underwent polymerisation with concomitant alkylation of its carboxylic acid function.
- Jumbam, Ndze D.,Maganga, Yamkela,Masamba, Wayiza,Mbunye, Nomthandazo I.,Mgoqi, Esethu,Mtwa, Sphumusa
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p. 387 - 392
(2018/09/06)
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- Composition FOR PREVENTING ALOPECIA AND ACTIVATING HAIR GROWTH
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The present invention provides a hair growth promoter comprising as an active ingredient, a compound having a chemical structure of general formula (1) or a pharmacologically acceptable salt thereof. In the general formula (1): R_1 is a saturated or unsaturated straight chain or branched C1-C10 alkyl group or hydroxy alkyl group; R_2 is hydrogen or a saturated or unsaturated straight chain or branched C1-C10 alkoxy or hydroxy alkoxy; X is hydrogen, hydroxy, or a saturated or unsaturated straight chain or branched C1-C10 alkyl group, alkoxy or hydroxyl alkoxy; R_3 and R_4 are each independently selected from R_5, hydrogen, aldehyde, and a saturated or unsaturated straight chain or branched alkyl, alkoxy, or hydroxy alkoxy; R_5 has a structure of # AAA #; R_6 is selected from hydrogen, and a saturated or unsaturated straight chain or branched C1-C10 alkyl, alkoxy, or hydroxy alkoxy; and one of R_3 and R_4 is hydrogen.COPYRIGHT KIPO 2017
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Paragraph 0116; 0142; 0143
(2018/02/16)
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- SKIN WHITENING AGENT CONTAINING NOVEL CYCLIC COMPOUND
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Provided is a derivative or a polyhydroxy cyclic compound represented by Formula I or a pharmacologically acceptable salt thereof with excellent whitening effects, comprising; wherein {circle around (A)} is derived from an aromatic cyclic compound, B is hydrogen, oxo (═O), amino (—NH2), imino (═NH), or a saturated or unsaturated straight or branched alkyl, alkoxy, monoalkylamino, or dialkylamino group having 1 to 10 carbon atoms, Cn, Cn+1and Cn+2 are three neighboring carbon atoms present in the aromatic cyclic compound, wherein n is a positive integer, R1 is hydrogen, hydroxy, or a saturated or unsaturated straight or branched alkyl or alkoxy group, X and Y are selected from a group consisting of hydrogen, hydroxy, and a saturated or unsaturated straight or branched alkoxy, or acyloxy group, and one of X and Y is hydrogen, R2, R3, R4 and R5 are each independently at least one substituent selected from a group consisting of hydrogen, alkyl, alkoxy, acyloxy, acyloxymethyl, oxo, hydroxy, vinyl, nitrile, carboxaldehyde, carbonitrile and aldehyde.
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Paragraph 0108; 0109; 0122; 0123
(2016/08/29)
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- New cyclic skin whiteninig agent
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In the present invention, provided is a skin whitening agent, which is easily synthesized without side effects for skin and has an outstanding effect of inhibiting pigmentation on skin due to an outstanding effect of inhibiting the creation of melanine where a cyclic derivative compound or pharmaceutically acceptable salt thereof has a chemical structure in formula (I) and is accordingly used to achieve the purpose of the present invention. In the present invention, provided is a cyclic derivative compound or pharmaceutically acceptable salt thereof, which has an effect of whitening skin and a chemical structure in formula (I) where A is derived from an aromatic cyclic compound; B is derived from among hydrogen, O which is oxo, NH_2 which is amino, NH which is imino, C1-C10 of saturated or unsaturated straight or branched chain alkyl group, alkoxy, mono alkyl amino group or dialkyl amino group; and C_n, C_n+1 and C_n+2 are three neighboring carbons in the cyclic compound wherein n is a positive integer.COPYRIGHT KIPO 2015
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Paragraph 0116; 0136-0137
(2016/11/21)
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- Structure activity relationship of brevenal hydrazide derivatives
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Brevenal is a ladder frame polyether produced by the dinoflagellate Karenia brevis. This organism is also responsible for the production of the neurotoxic compounds known as brevetoxins. Ingestion or inhalation of the brevetoxins leads to adverse effects such as gastrointestinal maladies and bronchoconstriction. Brevenal shows antagonistic behavior to the brevetoxins and shows beneficial attributes when administered alone. For example, in an asthmatic sheep model, brevenal has been shown to increase tracheal mucosal velocity, an attribute which has led to its development as a potential treatment for Cystic Fibrosis. The mechanism of action of brevenal is poorly understood and the exact binding site has not been elucidated. In an attempt to further understand the mechanism of action of brevenal and potentially develop a second generation drug candidate, a series of brevenal derivatives were prepared through modification of the aldehyde moiety. These derivatives include aliphatic, aromatic and heteroaromatic hydrazide derivatives. The brevenal derivatives were tested using in vitro synaptosome binding assays to determine the ability of the compounds to displace brevetoxin and brevenal from their native receptors. A sheep inhalation model was used to determine if instillation of the brevenal derivatives resulted in bronchoconstriction. Only small modifications were tolerated, with larger moieties leading to loss of affinity for the brevenal receptor and bronchoconstriction in the sheep model.
- Goodman, Allan,McCall, Jennifer R.,Jacocks, Henry M.,Thompson, Alysha,Baden, Daniel,Abraham, William M.,Bourdelais, Andrea
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p. 1839 - 1858
(2014/06/09)
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- Synthesis and structure-activity relationships of analogs of 2'-deoxy-2'- (3-methoxybenzamido)adenosine, a selective inhibitor of trypanosognal glycosomal glyceraldehyde-3-phosphate dehydrogenase
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In continuation of a project aimed at the structure-based design of drugs against sleeping sickness, analogs of 2'-deoxy-2'-(3- methoxybenzamido)adenosine (1) were synthesized and tested to establish structure-activity relationships for inhibiting glycosomal glyceraldehyde-3- phosphate dehydrogenase (GAPDH). Compound 1 was recently designed using the NAD: GAPDH complexes of the human enzyme and that of Trypanosoma brucei, the causative agent of sleeping sickness. In an effort to exploit an extra hydrophobic domain due to Val 207 of the parasite enzyme, several new 2'- amido-2'-deoxyadenosines were synthesized. Some of them displayed an interesting improvement in inhibitory activity compared to 1. Carbocyclic or acyclic analogs showed marked loss of activity, illustrating the importance of the typical (C-2'-endo) puckering of the ribose moiety. We also describe the synthesis of a pair of compounds that combine the beneficial effects of a 2- and 8-substituted adenine moiety on potency with the beneficial effect of a 2'-amide moiety on selectivity. Unfortunately, in both cases, IC50 values demonstrate the incompatibility of these combined modifications. Finally, introduction of a hydrophobic 5'-amide group on 5'-deoxyadenosine enhances the inhibition of the protozoan enzyme significantly, although the gain in selectivity is mediocre.
- Van Calenbergh,Verlinde,Seehens,De Bruyn,Callens,Blaton,Peeters,Rozenski,Hol,Herdewijn
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p. 3838 - 3849
(2007/10/02)
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