105-44-2Relevant academic research and scientific papers
Analogues of the Herbicide, N-Hydroxy- N-isopropyloxamate, Inhibit Mycobacterium tuberculosis Ketol-Acid Reductoisomerase and Their Prodrugs Are Promising Anti-TB Drug Leads
Kandale, Ajit,Patel, Khushboo,Hussein, Waleed M.,Wun, Shun Jie,Zheng, Shan,Tan, Lendl,West, Nicholas P.,Schenk, Gerhard,Guddat, Luke W.,McGeary, Ross P.
, p. 1670 - 1684 (2021/02/27)
New drugs to treat tuberculosis (TB) are urgently needed to combat the increase in resistance observed among the current first-line and second-line treatments. Here, we propose ketol-acid reductoisomerase (KARI) as a target for anti-TB drug discovery. Twenty-two analogues of IpOHA, an inhibitor of plant KARI, were evaluated as antimycobacterial agents. The strongest inhibitor of Mycobacterium tuberculosis (Mt) KARI has a Ki value of 19.7 nM, fivefold more potent than IpOHA (Ki = 97.7 nM). This and four other potent analogues are slow- and tight-binding inhibitors of MtKARI. Three compounds were cocrystallized with Staphylococcus aureus KARI and yielded crystals that diffracted to 1.6-2.0 ? resolution. Prodrugs of these compounds possess antimycobacterial activity against H37Rv, a virulent strain of human TB, with the most active compound having an MIC90 of 2.32 ± 0.04 μM. This compound demonstrates a very favorable selectivity window and represents a highly promising lead as an anti-TB agent.
Synthesis method of O-(3-chloro-2-propenyl) hydroxylamine
-
Paragraph 0037; 0049-0051; 0053-0055; 0057-0059; 0061-0063, (2021/05/29)
The invention belongs to the technical field of organic synthesis, and particularly discloses a synthesis method of O-(3-chloro-2-propenyl) hydroxylamine. The synthesis method comprises the following steps of: carrying out a heating reaction on a hydroxylamine solution and methyl isobutyl ketone to obtain methyl isobutyl ketoxime, then carrying out a reaction on the methyl isobutyl ketoxime, 1, 3-dichloropropene and an alkali liquor, after the reaction is finished, adjusting the reaction liquid to be weakly acidic by using acid, carrying out phase splitting, extracting a water phase by using methyl isobutyl ketone, combining organic phases, washing with water, removing water, and recovering the methyl isobutyl ketone to obtain the product 0-(3-chloro-2-propenyl) hydroxylamine. According to the method, methyl isobutyl ketone serves as an amino protective agent and a solvent at the same time, the molecular structure is not changed before and after the reaction, the defects that a large amount of ethyl acetate is consumed and acetic acid and sodium chloride are produced as byproducts in a traditional process can be overcome, and the method is an efficient, environment-friendly and high-yield 0-(3-chloro-2-propenyl) hydroxylamine synthesis method and is suitable for industrial production.
High-Throughput Screening of the Alkoxide/Oxime-Based Library: An Alternative to Organotin Compounds for the Alkoxysilane Condensation in Adhesives and Sealants
Colin, Boris,Lavastre, Olivier,Fouquay, Stéphane,Michaud, Guillaume,Simon, Frédéric,Brusson, Jean-Michel
supporting information, p. 300 - 309 (2019/02/19)
In this work, a high-throughput screening (HTS) method was used to discover new efficient catalysts to substitute organotin compounds (DBTDL) for the cross-linking of silyl-modified polymers (SMPs). We report here on the use of our HTS method to investigate a library of alkoxide/oxime systems with different metal/ligand (M/L) ratios. Among the 156 candidates tested, 40 interesting hits were detected. Then, the cross-linking times for the better hits were measured on the SMP. Some of these seem to be more efficient than DBTDL and exhibit a good stability during storage in cartridges. Thereby, a high efficiency of alkoxide/oxime systems was established that shows great potential for the generation of new ligands to provide new tin-free catalysts for the cross-linking of adhesives and sealants.
Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions
Zhu, Zhongzhi,Tang, Xiaodong,Cen, Jinghe,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 3767 - 3770 (2018/04/17)
A novel copper-catalyzed annulation of oxime acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(iii) intermediates were involved. In addition, this protocol proceeded under redox-neutral conditions and did not require additives or ligands.
Microwave-assisted efficient one-step synthesis of amides from ketones and benzoxazoles from (2-hydroxyaryl) ketones with acetohydroxamic acid using sulfuric acid as the catalyst
Madabhushi, Sridhar,Chinthala, Narsaiah,Vangipuram, Venkata Sairam,Godala, Kondal Reddy,Jillella, Raveendra,Mallu, Kishore Kumar Reddy,Beeram, China Ramanaiah
experimental part, p. 6103 - 6107 (2011/11/30)
Efficient one-step method for the synthesis of amides directly from ketones and benzoxazoles from (2-hydroxyaryl) ketones by the reaction of acetohydroxamic acid using sulfuric acid as catalyst was described.
Microwave enhanced synthesis of oximes from ketones
Mitra, Alok Kumar,De, Aparna,Karchaudhuri, Nilay
, p. 218 - 219 (2007/10/03)
Microwave enhanced synthesis of oximes from ketones in high yields is reported.
Process for producing aminopropanols
-
, (2008/06/13)
This invention relates to an improved process for the preparation of 3-aminopropanol and a primary amine by reacting a cyanoethyl ketoxime with hydrogen in the presence of a hydrogenation catalyst to generate the primary amine and aminopropanol. The sequence of reactions to form the aminopropanol and primary amine involves the reaction of hydroxylamine with a ketone to generate a ketoxime followed by reaction of acrylonitrile with the ketoxime to generate a cyanoethyl ketoxime followed by complete hydrogenation of the cyanoethyl ketoxime in the presence of a hydrogenation catalyst to generate the primary amine and aminopropanol. The significant advantage associated with this process is the high degree of selectivity to 3-aminopropanol and the primary amine.
Process for producing carbamates from oximes
-
, (2008/06/13)
A process for producing a carbamate is disclosed. In one embodiment, the process comprises contacting a mixture comprising a primary amine component, an urea component and a hydroxy nitrogen component, in particular at least one oxime, at conditions effective to form a carbamate. Certain novel carbamates are also disclosed.
Wanderungstendenzen cyclischer, polycyclischer und methylverzweigter Alkylreste bei der Beckmann-Umlagerung
Langhals, Heinz,Ruechardt, Christoph
, p. 3831 - 3854 (2007/10/02)
The migration aptitudes of polycyclic bridgehead groups, cycloalkyl groups as well as of β-, γ- and δ-branched alkyl groups in the Chapman variant of the Beckmann rearrangement were determined.From these data it is concluded that at transition state 2 the migrating group is not resembling a planarised carbenium ion R+, but rather a pentacoordinated carbonium ion structure.Because only small geometrical changes occur in the migrating group vertical stabilisation of charge at transition state is believed to have significant influence on the migration aptitudes.
