814-75-5Relevant academic research and scientific papers
Ring-closing metathesis approaches towards the total synthesis of rhizoxins
Altmann, Karl-Heinz,Liniger, Marc,Neuhaus, Christian M.
supporting information, (2020/10/18)
Efforts are described towards the total synthesis of the bacterial macrolide rhizoxin F, which is a potent tubulin assembly and cancer cell growth inhibitor. A significant amount of work was expanded on the construction of the rhizoxin core macrocycle by ring-closing olefin metathesis (RCM) between C(9) and C(10), either directly or by using relay substrates, but in no case was ringclosure achieved. Macrocycle formation was possible by ring-closing alkyne metathesis (RCAM) at the C(9)/C(10) site. The requisite diyne was obtained from advanced intermediates that had been prepared as part of the synthesis of the RCM substrates. While the direct conversion of the triple bond formed in the ring-closing step into the C(9)-C(10) E double bond of the rhizoxin macrocycle proved to be elusive, the corresponding Z isomer was accessible with high selectivity by reductive decomplexation of the biscobalt hexacarbonyl complex of the triple bond with ethylpiperidinium hypophosphite. Radical-induced double bond isomerization, full elaboration of the C(15) side chain, and directed epoxidation of the C(11)-C(12) double bond completed the total synthesis of rhizoxin F.
Preparation method of 3-methyl-3-penten-2-one
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Paragraph 0012-0016, (2019/01/08)
The invention discloses a preparation method of 3-methyl-3-penten-2-one. The preparation method comprises the following steps: with butanone as a raw material, performing 3-position halogenation to obtain 3-halobutanone (1), then performing a ketalation reaction to obtain 3-halobutanonediol (2), then performing a Grignard reaction to obtain a Grignard reagent, performing nucleophilic addition on the Grignard reagent and acetaldehyde, and performing intramolecular dehydration under the conditions of acid catalysis and heating to obtain a target product, namely the 3-methyl-3-penten-2-one (3). The preparation method has the advantages of easy obtainment of the raw material, a wide raw material source, simpleness, low preparation cost and suitability for industrial production; by the preparation method, the problems of high preparation cost and difficult industrial production in the prior art are solved.
METALLOENZYME INHIBITOR COMPOUNDS
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Page/Page column 265; 266, (2017/07/31)
The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.
Design, synthesis and antifungal activity of novel furancarboxamide derivatives
Wen, Fang,Jin, Hong,Tao, Ke,Hou, Taiping
, p. 244 - 251 (2016/05/24)
Twenty-seven novel furancarboxamide derivatives with a diphenyl ether moiety were synthesized and evaluated for their antifungal activity against Rhizoctonia solani, Botrytis cirerea, Valsa Mali and Sphaceloma ampelimum. Antifungal bioassay results indicated that most compounds had good or excellent fungicidal activities for R. solani and S. ampelimum at 20 mg L-1. Among synthesized compounds, compound 18e showed a greater inhibitory effect against S. ampelimum, with half maximal effective concentration (EC50) values of 0.020 mg L-1. This strong activity rivals currently used commercial fungicides, such as Boscalid and Carbendazim, and has great potential as a lead compound for future development of novel fungicides.
Stereodivergent Synthesis of Chromanones and Flavanones via Intramolecular Benzoin Reaction
Wen, Genfa,Su, Yingpeng,Zhang, Guoxiang,Lin, Qiqiao,Zhu, Yujin,Zhang, Qianqian,Fang, Xinqiang
supporting information, p. 3980 - 3983 (2016/09/09)
The strategy of stereodivergent reactions on racemic mixtures (stereodivergent RRM) was employed for the first time in intramolecular benzoin reactions and led to the rapid access of chromanones/flavanones with two consecutive stereocenters. The easily separable stereoisomers of the products were obtained with moderate to excellent enantioselectivities in a single step. Catechol type additives proved crucial in achieving the desired diastereo- and enantioselectivities.
Silica gel catalyzed α-bromination of ketones using N-bromosuccinimide: An easy and rapid method
Mohan Reddy, Bodireddy,Venkata Ramana Kumar, Velpula,Chinna Gangi Reddy, Nallagondu,Mahender Rao, Siripragada
, p. 179 - 182 (2014/02/14)
An easy and rapid method for the α-bromination of ketones using N-bromosuccinimide (NBS) catalyzed by silica gel in methanol under reflux conditions was developed. The expected products were formed in excellent isolated yields within a short period of time (5-20 min). Major advantages of the present procedure include use of inexpensive and readily available catalyst, exclusion of pre- and post-chemical treatment of catalyst and use of methanol as solvent instead of ethers and chlorinated solvents.
Aminoazabenzimidazoles, a Novel Class of Orally Active Antimalarial Agents
Hameed P, Shahul,Chinnapattu, Murugan,Shanbag, Gajanan,Manjrekar, Praveena,Koushik, Krishna,Raichurkar, Anandkumar,Patil, Vikas,Jatheendranath, Sandesh,Rudrapatna, Suresh S.,Barde, Shubhada P.,Rautela, Nikhil,Awasthy, Disha,Morayya, Sapna,Narayan, Chandan,Kavanagh, Stefan,Saralaya, Ramanatha,Bharath, Sowmya,Viswanath, Pavithra,Mukherjee, Kakoli,Bandodkar, Balachandra,Srivastava, Abhishek,Panduga, Vijender,Reddy, Jitender,Prabhakar,Sinha, Achyut,Jiménez-Díaz, María Belén,Martínez, María Santos,Angulo-Barturen, I?igo,Ferrer, Santiago,Sanz, Laura María,Gamo, Francisco Javier,Duffy, Sandra,Avery, Vicky M.,Magistrado, Pamela A.,Lukens, Amanda K.,Wirth, Dyann F.,Waterson, David,Balasubramanian,Iyer, Pravin S.,Narayanan, Shridhar,Hosagrahara, Vinayak,Sambandamurthy, Vasan K.,Ramachandran, Sreekanth
supporting information, p. 5702 - 5713 (2014/08/05)
Whole-cell high-throughput screening of the AstraZeneca compound library against the asexual blood stage of Plasmodium falciparum (Pf) led to the identification of amino imidazoles, a robust starting point for initiating a hit-to-lead medicinal chemistry effort. Structure-activity relationship studies followed by pharmacokinetics optimization resulted in the identification of 23 as an attractive lead with good oral bioavailability. Compound 23 was found to be efficacious (ED90 of 28.6 mg·kg-1) in the humanized P. falciparum mouse model of malaria (Pf/SCID model). Representative compounds displayed a moderate to fast killing profile that is comparable to that of chloroquine. This series demonstrates no cross-resistance against a panel of Pf strains with mutations to known antimalarial drugs, thereby suggesting a novel mechanism of action for this chemical class.
CXCR4 Receptor Antagonists
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Paragraph 0126; 0127, (2013/11/06)
Disclosed are compounds that are antagonists of the CXCR4 receptor.
CXCR4 RECEPTOR ANTAGONISTS
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Page/Page column 35, (2012/05/04)
The compounds of formula (I) are antagonists of the CXCR4 receptor Wherein R1, X, Y and R2 are as defined in the claims.
Oxidative bromination of ketones using ammonium bromide and oxone
MacHarla, Arun Kumar,Chozhiyath Nappunni, Rohitha,Marri, Mahender Reddy,Peraka, Swamy,Nama, Narender
supporting information; experimental part, p. 191 - 195 (2012/01/17)
A highly efficient, environmentally safe and economic method for selective α-monobromination of aralkyl, cyclic, acyclic, 1,3-diketones and β-keto esters and α,α-dibromination of 1,3-diketones and β-keto esters without catalyst is reported using ammonium bromide as a bromine source and oxone as an oxidant. The reaction proceeds at ambient temperature and yields range from moderate to excellent. Bromination of unsymmetrical ketones takes place at the less substituted α-position predominantly. Aromatisation of tetralones is also carried out with this reagent system.
