83612-52-6Relevant academic research and scientific papers
Antifungal Exploration of Quinoline Derivatives against Phytopathogenic Fungi Inspired by Quinine Alkaloids
Chen, Yong-Jia,Ma, Kun-Yuan,Du, Sha-Sha,Zhang, Zhi-Jun,Wu, Tian-Lin,Sun, Yu,Liu, Ying-Qian,Yin, Xiao-Dan,Zhou, Rui,Yan, Yin-Fang,Wang, Ren-Xuan,He, Ying-Hui,Chu, Qing-Ru,Tang, Chen
, p. 12156 - 12170 (2021/10/26)
Enlightened from our previous work of structural simplification of quinine and innovative application of natural products against phytopathogenic fungi, lead structure 2,8-bis(trifluoromethyl)-4-quinolinol (3) was selected to be a candidate and its diversified design, synthesis, and antifungal evaluation were carried out. All of the synthesized compounds Aa1-Db1 were evaluated for their antifungal activity against four agriculturally important fungi, Botrytis cinerea, Fusarium graminearum, Rhizoctonia solani, and Sclerotinia sclerotiorum. Results showed that compounds Ac3, Ac4, Ac7, Ac9, Ac12, Bb1, Bb10, Bb11, Bb13, Cb1. and Cb3 exhibited a good antifungal effect, especially Ac12 had the most potent activity with EC50 values of 0.52 and 0.50 μg/mL against S. sclerotiorum and B. cinerea, respectively, which were more potent than those of the lead compound 3 (1.72 and 1.89 μg/mL) and commercial fungicides azoxystrobin (both >30 μg/mL) and 8-hydroxyquinoline (2.12 and 5.28 μg/mL). Moreover, compound Ac12 displayed excellent in vivo antifungal activity, which was comparable in activity to the commercial fungicide boscalid. The preliminary mechanism revealed that compound Ac12 might cause an abnormal morphology of cell membranes, an increase in membrane permeability, and release of cellular contents. These results indicated that compound Ac12 displayed superior in vitro and in vivo fungicidal activities and could be a potential fungicidal candidate against plant fungal diseases.
Modular Cyclopentenone Synthesis through the Catalytic Molecular Shuffling of Unsaturated Acid Chlorides and Alkynes
Lee, Yong Ho,Denton, Elliott H.,Morandi, Bill
supporting information, p. 20948 - 20955 (2020/12/21)
We describe a general strategy for the intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis. Overall, this reaction is achieved via a molecular shuffling process involving an alkyne, an α,β-unsaturated acid chloride, which serves as both the alkene and carbon monoxide source, and a hydrosilane to create three new C-C bonds. This new carbon monoxide-free pathway delivers the products with excellent yields. Furthermore, the regioselectivity is complementary to conventional methods for cyclopentenone synthesis. In addition, a set of regio- and chemodivergent reactions are presented to emphasize the synthetic potential of this novel strategy.
Co(iii)-catalyzed: Z -selective oxidative C-H/C-H cross-coupling of alkenes with triisopropylsilylacetylene
Zhao, Tingxing,Qin, Dekun,Han, Weiguo,Yang, Shiping,Feng, Boya,Gao, Ge,You, Jingsong
supporting information, p. 6118 - 6121 (2019/06/03)
A Co(iii)-catalyzed direct oxidative C-H/C-H cross-coupling reaction of acrylamides with triisopropylsilylacetylene is presented. It is applicable to unsubstituted, internal and terminal acrylamides with a broad functionality tolerance. The feasibility of
Structure-anticonvulsant activity studies in the group of (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH3or 2-CH3
Gunia-Krzy?ak, Agnieszka,?elaszczyk, Dorota,Waszkielewicz, Anna M.,Pańczyk, Katarzyna,Marona, Henryk,Rapacz, Anna,Filipek, Barbara,?es?awska, Ewa,S?oczyńska, Karolina,P?kala, El?bieta,Nitek, Wojciech
, p. 471 - 482 (2016/12/30)
A series of twenty two (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH3or 2-CH3was designed, synthesized and evaluated for anticonvulsant activity in rodent models of seizures: maximal electroshock (MES) test, subcutaneous pentylenetetrazole (scPTZ) test, and 6-Hz test. There were identified three most active compounds: S-(2E)-N-(1-hydroxypropan-2-yl)-3-(2-methylphenyl)prop-2-enamide (5) (ED50MES = 42.56, ED50scPTZ = 58.38, ED506-Hz 44 mA = 42.27 mg/kg tested in mice after intraperitoneal (i.p.) administration); R,S-(2E)-3-(4-chlorophenyl)-N-(1-hydroxybutan-2-yl)prop-2-enamide (6) (ED50MES = 53.76, ED50scPTZ = 90.31, ED506-Hz 44 mA = 92.86 mg/kg mice, i.p.); and R,S-(2E)-3-(4-chlorophenyl)-N-(2-hydroxypropyl)prop-2-enamide (11) (ED50MES = 55.58, ED50scPTZ = 102.15, ED506-Hz 44 mA = 51.27 mg/kg mice, i.p.). Their structures and configurations were confirmed by crystal X-ray diffraction method. The structure-activity studies among the tested series showed that chlorine atom in position para or methyl group in position ortho of phenyl ring were beneficial for anticonvulsant activity. Methyl group in position para of phenyl ring decreased anticonvulsant activity in reported series of cinnamamide derivatives.
Copper-catalyzed highly selective synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[: B] thiazinones from 2-iodophenylcinnamamides and potassium sulfide
Liu, Wenjuan,Min, Hao,Zhu, Xiaoming,Deng, Guobo,Liang, Yun
supporting information, p. 9804 - 9808 (2017/12/08)
An efficient and practical procedure for the synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from easily available 2-iodophenylcinnamamides and potassium sulfide has been developed. In the presence of DBU, the reaction proceeds vi
Lithocholic acid-3-oxime ester compound, and preparation method and application thereof
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Paragraph 0026, (2017/12/27)
The invention discloses a lithocholic acid-3-oxime ester compound shown in a formula (I), and a preparation method thereof. The preparation method comprises the following steps: reacting substituted cinnamic acid and sulfoxide chloride to obtain substitut
Pd-Catalyzed α-Selective C-H Functionalization of Olefins: En Route to 4-Imino-β-Lactams
Kong, Wei-Jun,Liu, Yue-Jin,Xu, Hui,Chen, Yan-Qiao,Dai, Hui-Xiong,Yu, Jin-Quan
supporting information, p. 2146 - 2149 (2016/03/05)
Pd-catalyzed α-olefinic C-H activation of simple α,β-unsaturated olefins has been developed. 4-imino-β-lactam derivatives were readily synthesized via activation of α-olefinic C-H bonds with excellent cis stereoselectivity. A wide range of heterocycles at the β-position are compatible with this reaction. The product of 4-imino-β-lactam derivatives can be readily converted to 2-aminoquinoline which exists extensively in pharmaceutical drugs and natural products.
Preparation of conjugated 1,3-enynes by Rh(III)-catalysed alkynylation of alkenes via C-H activation
Collins, Karl D.,Lied, Fabian,Glorius, Frank
supporting information, p. 4459 - 4461 (2014/04/17)
An experimentally simple additive-free Rh(III)-catalysed direct alkynylation of alkenes has been developed. This protocol employs commercially available TIPS-EBX as the alkyne source, giving access to conjugated terminal enynes following a simple silyl-de
NEW ALKANOLAMIDE DERIVATIVES OF CINNAMIC ACID AND USE OF ALKANOLAMIDE DERIVATIVES OF CINNAMIC ACID FOR PREPARATION OF DRUGS
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Page/Page column 7; 8, (2014/05/24)
The invention presents new alkanolamide derivatives of cinnamic acid of general Formula 1 and the use of alkanolamide derivatives of cinnamic acid for production of drugs for neurological disorders like epilepsy and/or pain.
The synthesis of 3,4-disubstituted dihydroquinolin-2(1H)-one under metal-free conditions in aqueous solution
Wang, Hongyan,Sun, Bin,Yang, Jun,Wang, Jitao,Mao, Pu,Yang, Liangru,Mai, Wenpeng
, p. 542 - 545 (2014/12/10)
A novel route toward 3,4-disubstituted dihydroquinolin-2(1H )-ones via radical process has been developed in aqueous solution without metals. This method offers a new and simple route for the synthesis of skeleton of dihydroquinolin-2(1H )-one in one step
