cas 17082-09-6, CINNAMOYL CHLORIDE | Articles data

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AMIDE DERIVATIVES HAVING MULTIMODAL ACTIVITY AGAINST PAIN
The present invention relates to new compounds that show pharmacological activity towards the subunit α2δ of voltage-gated calcium channels (VGCC), especially the α2δ-1 subunit of voltage-gated calcium channels or dual activity towards the subunit α2δ of voltage-gated calcium channels (VGCC), especially the α2δ-1 subunit of voltage-gated calcium channels, and the μ-opiod receptor (MOR or mu-opioid). The invention is also related to the process for the preparation of said compounds as well as to compositions comprising them, and to their use as medicaments.
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Paragraph 0173

(2021/08/05)

Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives
This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3-dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta- of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho- and para-substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.
Li, Peng-Xiao,Liu, Guo-Yun,Liu, Ren-Min,Liu, Yue,Mu, Wen-Wen,Sun, Ya-Lei,Yang, Jie
(2022/01/13)

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation
A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.
Wu, Xiaofang,Zhou, Lei,Li, Fangshao,Xiao, Jing
p. 491 - 497
(2021/01/20)

In quest of small-molecules as potent non-competitive inhibitors against influenza
A series of scaffolds namely aurones, 3-indolinones, 4-quinolones and cinnamic acid-piperazine hybrids, was designed, synthesized and investigated in vitro against influenza A/H1N1pdm09 virus. Designed molecules adopted different binding mode i.e., in 430-cavity of neuraminidase, unlike sialic acid and oseltamivir in molecular docking studies. All molecules reduced the viral titer and exhibited non-cytotoxicity along with cryo-protective property towards MDCK cells. Molecules (Z)-2-(3′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2f), (Z)-2-(4′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2g) and 2-(2′-Methoxy-phenyl)-1H-quinolin-4-one (3a) were the most interesting molecules identified in this research, endowed with robust potencies showing low-nanomolar EC50 values of 4.0 nM, 6.7 nM and 4.9 nM, respectively, compared to reference competitive and non-competitive inhibitors: oseltamivir (EC50 = 12.7 nM) and quercetin (EC50 = 0.56 μM), respectively. Besides, 2f, 2g and 3a exhibited good neuraminidase inhibitory activity in sub-micromolar range (IC50 = 0.52 μM, 3.5 μM, 1.3 μM respectively). Moreover, these molecules were determined as non-competitive inhibitors similar to reference non-competitive inhibitor quercetin unlike reference competitive inhibitor oseltamivir in kinetics studies.
Malbari, Khushboo,Saha, Priyanka,Chawla-Sarkar, Mamta,Dutta, Shanta,Rai, Swita,Joshi, Mamata,Kanyalkar, Meena
(2021/07/19)

Meta-substituted piperlongumine derivatives attenuate inflammation in both RAW264.7 macrophages and a mouse model of colitis
Piperlongumine (PL) has been showed to have multiple pharmacological activities. In this study, we reported the synthesis of three series of PL derivatives, and evaluation of their anti-inflammatory effects in both lipopolysaccharide (LPS)-induced Raw264.7 macrophages and a dextran sulfate sodium (DSS)-induced mouse model of colitis. Our results presented that two meta-substituent containing derivatives 1–3 and 1–6, in which γ-butyrolactam replaced α,β-unsaturated δ-valerolactam ring of PL, displayed low cytotoxicity and effective anti-inflammatory activity. Molecular docking also showed that the meta-substituted derivative, compared with the corresponding ortho- or para-substituted derivative, had significant interactions with the amino acid residues of CD14, which was the core receptors recognizing LPS. In vitro and in vivo studies, 1–3 and 1–6 could inhibit the expression of pro-inflammatory cytokines, and the excessive production of reactive nitrogen species and reactive oxygen species. Oral administration of 100 mg/kg/day of 1–3 or 1–6 alleviated the severity of clinical symptoms of colitis in mice, and significantly reduced the colonic tissue damage to protect the colonic tissue from the DSS-induced colitis. These results suggested that meta-substituted derivatives 1–3 and 1–6 were potential anti-inflammatory agents, which may lead to future pharmaceutical development.
Gong, Zhaotang,Liu, Guoyun,Mu, Wenwen,Wang, Ziqing,Yang, Jie
(2021/11/16)

Cinnamate derivatives and application of cinnamate derivatives as tyrosinase inhibitors and gels
The invention discloses cinnamate derivatives and application of the cinnamate derivatives as tyrosinase inhibitors and gels, and the structural general formula of the cinnamate derivatives is shown in the specification, in the formula, X and Y independently represent any one of O, S and NH, wherein R1 and R2 independently represent any one of H, OH, methoxy, allyl and acetyl; R3 and R4 respectively and independently represent any one of H, OH, methoxy, tert-butyl dimethyl siloxy and carbethoxy, and R3 and R4 are not tert-butyl dimethyl silyl at the same time; and n is an integer from 2 to 5.The cinnamate derivatives disclosed by the invention have obvious inhibitory activity on the activity of mushroom tyrosinase diphenolic enzyme and the content of tyrosinase and melanin in melanoma cells of B16F10 mice, and can be used for preparing the tyrosinase inhibitors. Meanwhile, the cinnamate derivatives can form stable gels in olive oil and can be used as micromolecular gels for cosmeticsand the like.
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Paragraph 0077-0079; 0081; 0103-0106

(2020/08/02)

Pyrimidinethione-containing purine compound and application thereof
The invention discloses a pyrimidinethione-containing purine compound having a structure represented by a formula I shown in the specification and an application of the compound as a plant growth regulator. The compound represented by the formula I has excellent cell division activity and plant growth regulating activity of promoting rooting, increasing the yield and improving the quality, and canbe widely used for rooting, seedling strengthening, yield increasing and quality improvement of crops such as grain, cotton, fruits and vegetables or plants through the manners of treating seeds, being sprayed to roots and stem leaves, at the same time, the compound represented by the formula I has a bactericidal effect, and the characteristics of safe use, low costs, and significant effects.
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Paragraph 0018; 0023-0025

(2020/01/25)

The potential role of the 5,6-dihydropyridin-2(1: H)-one unit of piperlongumine on the anticancer activity
Piperlongumine (PL), a potent anticancer agent from the plant long pepper (Piper longum), contains the 5,6-dihydropyridin-2(1H)-one heterocyclic scaffold and cinnamoyl unit. In this paper, we synthesized a series of PL analogs and evaluated their cytotoxicity against cancer cells for the sake of exploring which pharmacophore plays a more potent role in enhancing the anticancer activities of PL. These results illustrated that the position effect, not the electronic effect, of substituents plays a certain role in the cytotoxicity of PL and its analogs. More important, the 5,6-dihydropyridin-2(1H)-one unit, a potent pharmacophore in enhancing the antiproliferative activities of PL, could react with cysteamine and lead to ROS generation, and then bring about the occurrence of ROS-induced downstream events, followed by cell cycle arrest and apoptosis. This work suggests that introducing a lactam unit containing Michael acceptors may be a potent strategy to enhancing the anticancer activity of drugs. This journal is
Li, Peng-Xiao,Liu, Guo-Yun,Liu, Yue,Mu, Wen-Wen,Yang, Jie
p. 42128 - 42136
(2020/12/09)

Controllable phosphorylation of thioesters: Selective synthesis of aryl and benzyl phosphoryl compounds
The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.
Xu, Kaiqiang,Liu, Long,Li, Zhaohui,Huang, Tianzeng,Xiang, Kang,Chen, Tieqiao
p. 14653 - 14663
(2020/12/29)

A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides
For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.
Wu, Xiaofang,Zhou, Lei,Yang, Ruoqi,Guo, Fengzhe,Tang, Zi-Long,Xiao, Jing
p. 301 - 304
(2020/01/29)

New coumarin/sulfocoumarin linked phenylacrylamides as selective transmembrane carbonic anhydrase inhibitors: Synthesis and in-vitro biological evaluation
Two novel series of phenylacrylamide linked coumarins and sulfocoumarins (6a-p, 8a-i, and 14a-g) were synthesized and evaluated against four physiologically relevant human carbonic anhydrases (hCAs, EC 4.2.1.1), isoforms hCA I, hCA II, hCA IX and hCA XII for their inhibitory action. All new compounds when screened for carbonic anhydrase inhibitory activity have shown selective inhibition towards the tumor associated isoforms hCA IX and XII over CA I and II, with inhibition constants in the submicromolar to low nanomolar range. Compound 6b and 14g exhibited significant inhibition with low nanomolar potency against hCA IX, whereas 6k was effective against hCA XII. Compounds 6b, 14g and 6k may be considered as lead molecules for future development of cancer therapeutics based on a novel mechanism of action.
Angeli, Andrea,Arifuddin, Mohammed,Singh, Priti,Supuran, Claudiu T.,Swain, Baijayantimala
(2020/07/03)

Synthesis and biological evaluation of 2,2-dimethylbenzopyran derivatives as potent neuroprotection agents
The development of novel neuroprotection agents is of great significance for the treatment of ischemic stroke. In this study, a series of compounds comprising 2,2-dimethylbenzopyran groups and cinnamic acid groups have been synthesized. Preferential combination principles and bioisostere that improved the neuroprotective effect of the compounds were identified for this series via biological activity assay in vitro. Meanwhile, a functional reversal group of the acrylamide amide resulted in the most active compounds. Among them, BN-07 significantly improved the morphology of neurons and obviously increased cell survival rate of primary neurons induced by oxygen glucose deprivation (OGD), superior to clinically used anti-ischemic stroke drug edaravone (Eda). Overall, our findings may provide an alternative strategy for the design of novel anti-ischemic stroke agents with more potency than Eda.
Du, Fangyu,Zhou, Qifan,Fu, Xiaoxiao,Shi, Yajie,Chen, Yuanguang,Fang, Wuhong,Yang, Jingyu,Chen, Guoliang
p. 2498 - 2508
(2019/02/01)

Synthesis, preliminarily biological evaluation and molecular docking study of new Olaparib analogues as multifunctional PARP-1 and cholinesterase inhibitors
A series of new Olaparib derivatives was designed and synthesized, and their inhibitory activities against poly (ADP-ribose) polymerases-1 (PARP-1) enzyme and cancer cell line MDA-MB-436 in vitro were evaluated. The results showed that compound 5l exhibited the most potent inhibitory effects on PARP-1 enzyme (16.10 ± 1.25 nM) and MDA-MB-436 cancer cell (11.62 ± 2.15 μM), which was close to that of Olaparib. As a PARP-1 inhibitor had been reported to be viable to neuroprotection, in order to search for new multitarget-directed ligands (MTDLs) for the treatment of Alzheimer’s disease (AD), the inhibitory activities of the synthesized compounds against the enzymes AChE (from electric eel) and BChE (from equine serum) were also tested. Compound 5l displayed moderate BChE inhibitory activity (9.16 ± 0.91 μM) which was stronger than neostigmine (12.01 ± 0.45 μM) and exhibited selectivity for BChE over AChE to some degree. Molecular docking studies indicated that 5l could bind simultaneously to the catalytic active of PARP-1, but it could not interact well with huBChE. For pursuit of PARP-1 and BChE dual-targeted inhibitors against AD, small and flexible non-polar groups introduced to the compound seemed to be conducive to improving its inhibitory potency on huBChE, while keeping phthalazine-1-one moiety unchanged which was mainly responsible for PARP-1 inhibitory activity. Our research gave a clue to search for new agents based on AChE and PARP-1 dual-inhibited activities to treat Alzheimer’s disease.
Gao, Cheng-Zhi,Dong, Wei,Cui, Zhi-Wen,Yuan, Qiong,Hu, Xia-Min,Wu, Qing-Ming,Han, Xianlin,Xu, Yao,Min, Zhen-Li
p. 150 - 162
(2018/11/30)

A cinnamic acid naphthalene dicarboxylic acid imide ester compound and use thereof
The invention discloses naphthalene cinnamate dicarboximide ester compounds which have a structure as shown in a formula I; the compounds can be used as a plant growth regulator. The compounds as shown in the formula I have excellent functions of promoting germination, rooting as well as production-increasing and quality-improving, has a good bactericidal effect, and has control effects especially for phytophthora capsici, wheat scab, apple ring spot and cucumber blight disease at 200ppm, and the like, thus being widely used for disease prevention and yield improvement in agriculture or forestry. The formula I is described in the description.
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Paragraph 0017-0020

(2019/07/04)

Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data
Amides are important natural products which occur in a few plant families. Piplartine and piperine, major amides in Piper tuberculatum and P. nigrum, respectively, have shown a typical N-CO cleavage when analyzed by EI-MS or HRESI-MS. In this study several synthetic analogs of piplartine and piperine were subjected to both types of mass spectrometric analysis in order to identify structural features influencing fragmentation. Most of the amides showed an intense signal of the protonated molecule [M + H]+ when subjected to both HRESI-MS and EI-MS conditions, with a common outcome being the cleavage of the amide bond (N-CO). This results in the loss of the neutral amine or lactam and the formation of aryl acylium cations. The mechanism of N-CO bond cleavage persists in α,β-unsaturated amides because of the stability caused by extended conjugation. Computational methods determined that the protonation of the piperamides and their derivatives takes place preferentially at the amide nitrogen supporting the dominant the N-CO bond cleavage.
Fokoue,Marques,Correia,Yamaguchi,Qu,Aires-De-Sousa,Scotti,Lopes,Kato
p. 21407 - 21413
(2018/06/26)

Design, synthesis and evaluation against Chikungunya virus of novel small-molecule antiviral agents
Chikungunya virus is a re-emerging arbovirus transmitted to humans by mosquitoes, responsible for an acute flu-like illness associated with debilitating arthralgia, which can persist for several months or become chronic. In recent years, this viral infection has spread worldwide with a previously unknown virulence. To date, no specific antivirals treatments nor vaccines are available against this important pathogen. Starting from the structures of two antiviral hits previously identified in our research group with in silico techniques, this work describes the design and preparation of 31 novel structural analogues, with which different pharmacophoric features of the two hits have been explored and correlated with the inhibition of Chikungunya virus replication in cells. Structure-activity relationships were elucidated for the original scaffolds, and different novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these promising novel structures as antiviral agents against Chikungunya virus.
Tardugno, Roberta,Giancotti, Gilda,De Burghgraeve, Tine,Delang, Leen,Neyts, Johan,Leyssen, Pieter,Brancale, Andrea,Bassetto, Marcella
p. 869 - 874
(2018/01/18)

Cinnamoyl indoline compounds and application of cinnamoyl indoline compounds to preparation of glaucoma drugs
The invention belongs to the field of therapeutic drugs for ophthalmic diseases and particularly relates to an application of cinnamoyl indoline compounds to preparation of glaucoma lesion treating orimproving drugs. In-vitro cell culture experiment and i
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Paragraph 006; 0028; 0031; 0032

(2018/04/02)

Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters
An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented controlling factor for para-selective C-H activation/borylation.
Hoque, Md Emdadul,Bisht, Ranjana,Haldar, Chabush,Chattopadhyay, Buddhadeb
supporting information
p. 7745 - 7748
(2017/06/21)

Synthesis and evaluation of novel ascorbyl cinnamates as potential anti-oxidant and antimicrobial agents
Abstract: An efficient preparation procedure has been proposed for the synthesis of 5,6-di-O-cinnamyl-l-ascorbic acid ester (5,6-CA–AA) and 2-O-cinnamyl-l-ascorbic acid ester (2-CA–AA) via ascorbic acid (AA) and cinnamic acid (CA), and their anti-oxidant and antibacterial activities were also investigated. Among the factors affecting the synthesis efficiency of 5,6-CA–AA and 2-CA–AA, reaction solvent and substrate molar ratio were very important, resulting in 76 and 54% total yield, respectively. Further studies indicated that 5,6-CA–AA maintained the inherent inhibitory ability of AA in α, α-diphenyl-β-picrylhydrazyl radical scavenging assay. Also, it had stronger scavenging activity against hydroxyl radicals than that of standard tert-butylhydroquinone (EC50: 7.84 vs. 8.38?mM). In addition, 5,6-CA–AA and 2-CA–AA possessed comparable antibacterial activity to that of CA. Significantly, the application of ascorbyl cinnamate could retard the lipid oxidation of peanut oil and pork, and the corresponding perioxide value and thiobarbituric acid reactive substance content decreased by 32.0 and 56.5%, respectively. Moreover, the microbial reproduction of the pork treated with mixed ascorbyl cinnamate was attenuated to some extent. These investigations will pave the way for designing more efficient bifunctional derivatives of AA and CA.
Hui, Ailing,Wang, Yuan,Zhu, Kaili,Chen, Jingchao,Fan, Qingping,Zhou, An,Zhang, Wencheng,Wu, Zeyu
p. 5901 - 5916
(2017/09/23)

Novel 4-(4-substituted amidobenzyl)furan-2(5H)-one derivatives as topoisomerase I inhibitors
In this study, two series of novel 4-(4-substituted amidobenzyl)furan-2(5H)-one derivatives containing an α,β-unsaturated lactone fragment were synthesized and screened for Topo I inhibition and antitumor activity. The topoisomerase I inhibitory activities and cytotoxicities against three human cancer cell lines (MCF-7,Hela,A549) were evaluated. The results revealed that series 2, compounds bearing an exocyclic double bond on the furanone ring, generally showed more potent activity than series 1, compounds lacking an exocyclic double bond. Several compounds of series 2 possess significant Topo I inhibitory activity and potent antiproliferative activity against cancer cell lines. Further mechanism studies of the most active compound of series 2 (B-15) indicated that synthetic compounds can not only stabilize the drug-enzyme-DNA covalent ternary complex as well as camptothecin, but also interfere with the binding between Topo I and DNA. The binding patterns of these compounds with Topo I and structure-activity relationships are discussed.
Peng, Cheng-Kang,Zeng, Ting,Xu, Xing-Jun,Chang, Yi-Qun,Hou, Wen,Lu, Kuo,Lin, Hui,Sun, Ping-Hua,Lin, Jing,Chen, Wei-Min
p. 187 - 199
(2017/01/06)

Synthesis and in?vitro and in?vivo antitumour activity study of 11-hydroxyl esterified bergenin/cinnamic acid hybrids
Fourteen bergenin/cinnamic acid hybrids were synthesized, characterized and evaluated for their antitumour activity both in?vitro and in?vivo. The most potent compound, 5c, arrested HepG2 cells (IC50?=?4.23?±?0.79?μM) in the G2/M phase and induced cellular apoptosis. Moreover, compound 5c was also found to suppress the tumour growth in Heps xenograft-bearing mice with low toxicity. In the mechanistic study, 5c administration ignited a mitochondria-mediated apoptosis pathway of HepG2 cell death. Furthermore, 5c activated Akt-dependent pathways and further decreased the expression of the Bcl-2 family of proteins. The downstream mitochondrial p53 translocation was also significantly activated, accompanied by an increase of the caspase-9, caspase-3 activation. These data imply that bergenin/cinnamic acid hybrids could serve as novel Akt/Bcl-2 inhibitors for further preclinical studies.
Liang, Chengyuan,Pei, Shaomeng,Ju, Weihui,Jia, Minyi,Tian, Danni,Tang, Yonghong,Mao, Gennian
p. 319 - 328
(2017/04/11)

Bioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection
A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Structure-activity relationship was derived also. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Eight compounds showed the higher average activity with average EC50 values of 17.4-28.6 μg/mL for the fungi than kresoxim-methyl, a commercial fungicide standard, and ten compounds were much more active than commercial fungicide standards carbendazim against P. grisea or kresoxim-methyl against both P. grisea and Valsa Mali. Compounds C1 and C2 showed the higher activity with average EC50 values of 17.4 and 18.5 μg/mL and great potential for development of new plant antifungal agents. The structure-activity relationship analysis showed that both the substitution pattern of the phenyl ring and the alkyl group in the alcohol moiety significantly influences the activity. There exists complexly comprehensive effect between the substituents on the phenyl ring and the alkyl group in the alcohol moiety on the activity. Thus, cinnamic acid esters showed great potential the development of new antifungal agents for plant protection due to high activity, natural compounds or natural compound framework, simple structure, easy preparation, low-cost and environmentally friendly.
Zhou, Kun,Chen, Dongdong,Li, Bin,Zhang, Bingyu,Miao, Fang,Zhou, Le
(2017/04/26)

Formal (4+1) Cycloaddition and Enantioselective Michael–Henry Cascade Reactions To Synthesize Spiro[4,5]decanes and Spirooxindole Polycycles
Spiro[4,5]decanes and polycyclic compounds bearing spiro[4,5]decane systems are important biofunctional molecules. Described are diastereoselective formal (4+1) cycloaddition reactions to afford oxindole-functionalized spiro[4,5]decanes and organocatalyti
Huang, Ji-Rong,Sohail, Muhammad,Taniguchi, Tohru,Monde, Kenji,Tanaka, Fujie
supporting information
p. 5853 - 5857
(2017/05/12)

Pd-Catalyzed α-Selective C-H Functionalization of Olefins: En Route to 4-Imino-β-Lactams
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.
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)

Design, synthesis and antimycobacterial activity of novel imidazo[1,2-a]pyridine amide-cinnamamide hybrids
We report herein the design and synthesis of a series of novel imidazo[1,2- A]pyridine amide-cinnamamide hybrids linked via an alkyl carbon chain. All 38 new hybrids were evaluated for their antimycobacterial activity against M. tuberculosis (MTB) H37Rv ATCC 27294 using the microplate Alamar Blue assay (MABA). Although the hybrids are less active than the two reference compounds, the promising activity (MICs: 4 μg/mL) of 2,6-dimethylimidazo[1,2-a]pyridine amide-cinnamamide hybrids 11e and 11k could be a good starting point to further find new lead compounds against multi-drug-resistant tuberculosis.
Li, Linhu,Li, Zhuorong,Liu, Mingliang,Shen, Weiyi,Wang, Bin,Guo, Huiyuan,Lu, Yu
(2016/02/05)

A cinnamic acid pyridine ethyl ester compound and use thereof (by machine translation)
The invention discloses a structure as shown in formula I the cinnamic acid pyridine ethyl ester compounds and salts thereof, In the formula: X is H, Y is H; X is Cl, Y is Cl; the salt is inorganic acid salt or organic acid salt. The compounds of formula
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Paragraph 0025; 0026; 0027

(2016/11/28)

Solvent-free regioselective synthesis of novel isoxazoline and pyrazoline N-substituted saccharin derivatives under microwave irradiation
Novel isoxazoline and pyrazoline derivatives of N-substituted saccharin were synthesized in good yields by 1,3-dipolar cycloaddition of N-crotonoyl- or N-cinnamoylsaccharin as dipolarophile to arylnitrile oxides or nitrile imines using p-HAP300 as catalyst under solvent-free microwave conditions. In this process, the yields were significantly improved compared to classical conditions without alteration of the selectivity. The regioselectivity as well as the nonthermal specific microwave effect are discussed.
Saber, Aziza,Driowya, Mohsine,Alaoui, Soukaina,Marzag, Hamid,Demange, Luc,álvarez, Eleuterio,Benhida, Rachid,Bougrin, Khalid
p. 31 - 40
(2016/03/22)

Synthesis and biological evaluation of N-cinnamoyl and mandelate metformin analogues
A series of N,N-dimethyl-N1-[3-(substituted phenyl)-1-oxo-2-propenyl]biguanides were synthesized by coupling a solution of metformin in pyridine with different cinnamoyl chloride derivatives in ether for 3 h in addition to synthesis of some five molecules of metformin-mandelates. All the synthesized cinnamoyl metformins and a few metformin-mandelates were characterized by IR, NMR and Mass spectroscopic techniques. All the synthesized compounds were also evaluated for their antioxidant activity by DPPH scavenging method and nitric oxide scavenging method. All the compounds exhibited good antioxidant activity.
Anitha Kumari,Bharathi,Prabhu,Ponnudurai
p. 1895 - 1898
(2016/07/06)

ACRYLATE COMPOUND HAVING PHOTOREACTIVE GROUP, PHOTOREACTIVE ACRYLATE POLYMER AND PHOTO-ALIGNMENT LAYER COMPRISING THE SAME
The present invention relates to an acrylate compound which has excellent orientation and orientation speed, properties that an orientation direction easily changes toward a polarizing direction, excellent solubility in an organic solvent, and processability; to a photoreactive acrylate polymer and to a photo-alignment layer comprising the same.
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(2016/10/09)

Preparation method of acyl chloride
The invention relates to a preparation method of acyl chloride. The method comprises the following steps that 1, carboxylic acid is added into a reactor, or carboxylic acid is dissolved in organic solvent, a device is connected, and the temperature is raised to 100 DGE C-250 DEG C; 2, phosgene is introduced into the reactor for a reaction, and then the temperature is decreased to room temperature; 3, nitrogen is introduced, residual phosgene and hydrogen chloride are cleaned away, reaction liquid which is reacted without solvent is subjected to decompression distillation and purification directly, and needed acyl chloride is obtained; reaction liquid which is reacted with the solvent is subjected to decompression distillation to remove the solvent, and needed acyl chloride is obtained. According to the preparation method of acyl chloride, no catalyst is added, the risks that in the synthesizing process, due to the fact that the catalyst is dissolved, color of the finial product of acyl chloride is increased, and the catalyst is remained in late products are avoided, after the reaction is finished, high-quality acyl chloride can be obtained through decompression distillation, and the technological process is simple; due to the fact that in the whole technological process, except for absorbable and available phosgene, hydrogen chloride and carbon dioxide, no other three waste is discharged, the preparation method of acyl chloride is environmentally friendly, and the good implement value is achieved.
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Paragraph 0068; 0069

(2016/11/28)

Rhodium(III)-Catalyzed Cascade Cyclization/Electrophilic Amidation for the Synthesis of 3-Amidoindoles and 3-Amidofurans
A rhodium(III)-catalyzed cascade cyclization/electrophilic amidation using N-pivaloyloxylamides as the electrophilic nitrogen source has been developed. This protocol provides an efficient route for the synthesis of 3-amidoindoles and 3-amidofurans under mild conditions with good functional group tolerance. The synthetic utility of this reaction has been demonstrated through the derivatization of the 3-amidoindoles to several heterocycle-fused indoles.
Hu, Zhiyong,Tong, Xiaofeng,Liu, Guixia
supporting information
p. 2058 - 2061
(2016/06/01)

1 - (cinnamoyl) - 4-piperidyl amide piperazine compound and its preparation method
The invention discloses a 1-(cinnamoyl)-4-piperidyl amide piperazidine compound and a preparation method thereof. The 1-(cinnamoyl)-4-piperidyl amide piperazidine compound is a compound shown as the formula (I) and pharmaceutically acceptable salt. The co
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Paragraph 0018-0020

(2016/10/08)

A α-pinene derivatives and its preparation method and application (by machine translation)
This invention has offered a kind of α-pinene derivatives, the derivatives of formula I such as a structural formula shown in formula II. Said α-pinene derivatives by the reduction, the organic acid ester and the like introduced into the α-pinene in the molecule skeleton to obtain new derivatives. Research shows that in vitro anti-tumor activity, the present invention provides the α-pinene derivatives to liver cancer cells has significant inhibition function, as the preparation of anti-tumor compound or its pharmaceutically acceptable salt, hydrate, solvate or prodrug, has good application prospect. Type I ;? ? ? Type II. (by machine translation)
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Paragraph 0182; 0183

(2016/10/09)

O-cinnamoyl-fluorobenzene salicylic amide compound and its in the preparation of anti-human placenta down cancer application of the medicament
The invention discloses an O-cinnamoyl-fluorobenzene salicylamide compound as shown in a formula (I) and an application thereof in preparation of an antitumor medicament, especially a medicament for fighting human placental choriocarcinoma. The O-cinnamoy
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Paragraph 0047; 0049

(2016/10/10)

Effect of azo and ester linkages on rod shaped Schiff base liquid crystals and their photophysical investigations
Two new series of rod shaped Schiff base containing liquid crystal compounds with azo and ester linkages have been synthesized and characterized respectively. The rod like molecules containing cinnamate linkages with four different alkyl spacers (n?=?6, 8
Selvarasu, Chinnaiyan,Kannan, Palaninathan
p. 234 - 240
(2016/07/12)

Synthesis and hypoglycemic activity of 9-O-(lipophilic group substituted) berberine derivatives
A series of 9-O-(lipophilic group substituted) berberine derivatives were synthesized and evaluated for their cytotoxicity and hypoglycemic activity against HepG2 cells. All the results indicated that most of the synthesized compounds exhibited lower cytotoxicity and a certain degree of hypoglycemic activity. Especially the compounds 5g and 5h displayed dramatically increased hypoglycemic activity compared with berberine, and the cytotoxicity maintained or even lower than berberine, indicating that they are potential candidates for new anti-type 2 diabetes mellitus drugs.
Zhang, Shanshan,Wang, Xiaohong,Yin, Weicheng,Liu, Zhenbao,Zhou, Mi,Xiao, Daipeng,Liu, Yanfei,Peng, Dongming
supporting information
p. 4799 - 4803
(2016/09/13)

O-cinnamoyl-fluorobenzene salicylic amide compound and its in the preparation of anti-leucocythemia application
The invention discloses O-cinnamyl-fluorophenylsalicylamide compounds disclosed as Formula (I) and application thereof in preparing anti-leukaemia drugs. The invention provides a preparation method of the O-cinnamyl-fluorophenylsalicylamide compounds; the
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Paragraph 0050

(2016/10/27)

Synthesis, characterization, and anti-inflammatory activities of methyl salicylate derivatives bearing piperazine moiety
In this study, a new series of 16 methyl salicylate derivatives bearing a piperazine moiety were synthesized and characterized. The in vivo anti-inflammatory activities of target compounds were investigated against xylol-induced ear edema and carrageenan-induced paw edema in mice. The results showed that all synthesized compounds exhibited potent anti-inflammatory activities. Especially, the anti-inflammatory activities of compounds M15 and M16 were higher than that of aspirin and even equal to that of indomethacin at the same dose. In addition, the in vitro cytotoxicity activities and anti-inflammatory activities of four target compounds were performed in RAW264.7 macrophages, and compound M16 was found to significantly inhibit the release of lipopolysaccharide (LPS)-induced interleukin (IL)-6 and tumor necrosis factor (TNF)-α in a dose-dependent manner. In addition, compound M16 was found to attenuate LPS induced cyclooxygenase (COX)-2 up-regulation. The current preliminary study may provide information for the development of new and safe anti-inflammatory agents.
Li, Jingfen,Yin, Yong,Wang, Lisheng,Liang, Pengyun,Li, Menghua,Liu, Xu,Wu, Lichuan,Yang, Hua
(2016/12/02)

O-cinnamoyl-fluorobenzene salicylic amide compound and its in the preparation of anti-cervic application of the medicament
The invention discloses an O-cinnamoyl-fluorobenzene salicylamide compound as shown in the formula (I) in the specification, and discloses application of the O-cinnamoyl-fluorobenzene salicylamide compound in preparing an anti-tumor medicine, in particula
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Paragraph 0047; 0049

(2017/02/09)

O-cinnamoyl-fluorobenzene salicylic amide compound and its in the preparation of anti-human cervical squamose cancer application of the medicament
The invention discloses an O-cinnamoyl-fluorobenzene salicylamide compound shown in a formula (I) in the specification, and also discloses an application of the compound in preparation of drugs for resisting tumors, particularly cervical squamous cancer.
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Paragraph 0019; 0047; 0049

(2017/02/09)

Prevention and treatment of Alzheimer's disease drug gx50 potential, gx51, gx52, gx180 chemical synthesis method
The invention relates to a chemical synthetic method of potential medicines g x50, g x52, g x 52, g x 180 for preventing and treating Alzheimer disease. Aryl acrylic acid and aryl ethylamine serve as origination raw materials. The chemical synthetic metho
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Paragraph 0018

(2017/04/08)

Design, synthesis and cytotoxic evaluation of novel imatinib amide derivatives that target Abl kinase
Novel imatinib amide derivatives (a1-28, b1-9) were synthesized and evaluated for their biological activities. All compounds were characterized by 1H NMR, MS and elemental analysis. Among all the derivatives, compounds a4, a10, a21, b1 and b2 displayed the most significant ability of inhibiting K562 cell proliferation with the IC50 values of 0.67, 0.66, 0.65, 0.59 and 0.62 μM, respectively, indicating that these compounds were potent inhibitors of Bcr-Abl in leukemic K562 cells, comparable to the reference compound imatinib. Molecular docking study was performed to position compounds a21 and b1 into the active site of Abl to determine the probable binding modes
Yao, Ri-Sheng,Guan, Qiu-Xiang,Lu, Xiao-Qin,Ruan, Ban-Feng
p. 20 - 28
(2015/03/31)

Design, synthesis and antibacterial activity of cinnamaldehyde derivatives as inhibitors of the bacterial cell division protein FtsZ
In an attempt to discover potential antibacterial agents against the increasing bacterial resistance, novel cinnamaldehyde derivatives as FtsZ inhibitors were designed, synthesized and evaluated for their antibacterial activity against nine significant pathogens using broth microdilution method, and their cell division inhibitory activity against four representative strains. In the in vitro antibacterial activity, the newly synthesized compounds generally displayed better efficacy against Staphylococcus aureus ATCC25923 than the others. In particular, compounds 3, 8 and 10 exerted superior or comparable activity to all the reference drugs. In the cell division inhibitory activity, all the compounds showed the same trend as their in vitro antibacterial activity, exhibiting better activity against S. aureus ATCC25923 than the other strains. Additionally, compounds 3, 6, 7 and 8 displayed potent cell division inhibitory activity with an MIC value of below 1 1/4g/mL, over 256-fold better than all the reference drugs.
Li, Xin,Sheng, Juzheng,Huang, Guihua,Ma, Ruixin,Yin, Fengxin,Song, Di,Zhao, Can,Ma, Shutao
p. 32 - 41
(2015/05/13)

Synthesis of Piperlongumine Analogues and Discovery of Nuclear Factor Erythroid 2-Related Factor 2 (Nrf2) Activators as Potential Neuroprotective Agents
The cellular antioxidant system plays key roles in blocking or retarding the pathogenesis of adult neurodegenerative disorders as elevated oxidative stress has been implicated in the pathophysiology of such diseases. Molecules with the ability in enhancing the antioxidant defense thus are promising candidates as neuroprotective agents. We reported herein the synthesis of piperlongumine analogues and evaluation of their cytoprotection against hydrogen peroxide- and 6-hydroxydopamine-induced neuronal cell oxidative damage in the neuron-like PC12 cells. The structure-activity relationship was delineated after the cytotoxicity and protection screening. Two compounds (4 and 5) displayed low cytotoxicity and confer potent protection of PC12 cells from the oxidative injury via upregulation of a panel of cellular antioxidant molecules. Genetically silencing the transcription factor Nrf2, a master regulator of the cellular stress responses, suppresses the cytoprotection, indicating the critical involvement of Nrf2 for the cellular action of compounds 4 and 5 in PC12 cells.
Peng, Shoujiao,Zhang, Baoxin,Meng, Xianke,Yao, Juan,Fang, Jianguo
p. 5242 - 5255
(2015/08/03)

Synthesis and antibacterial activity of 4'3-O-(trans-β-arylacrylamido)carbamoyl azithromycin analogs
Novel 4'3-O-(trans-β-arylacrylamido)carbamoyl azithromycin analogs were designed, synthesized and evaluated for their antibacterial activity against nine significant pathogens using broth microdilution method. A majority of these derivatives maintained the activity of azithromycin against susceptible Streptococcus pyogenes and all the compounds demonstrated remarkably improved activity compared with the references against all the three phenotypes of resistant Streptococcus pneumoniae. In particular, compound 24 exhibited the most potent activity against susceptible Staphylococcus aureus (MIC = 0.5 μg/mL), S. pneumoniae (MIC = 0.06 μg/mL) and S. pyogenes (MIC = 0.25 μg/mL). The most active compound 7 (MIC = 0.015 μg/mL) against resistant S. pneumoniae expressing the mefA gene, exhibited 512 and 256-fold more potent activity than erythromycin and azithromycin, respectively. Compounds 28 (MIC = 0.5 μg/mL), 29 (MIC = 0.25 μg/mL) and 30 (MIC = 0.5 μg/mL) demonstrated potent activity against resistant S. pneumoniae expressing the ermB gene, which were 256, 512 and 256-fold better than the references, respectively.
Yan, Mi,Ma, Xiaodong,Dong, Ruiqian,Li, Xin,Zhao, Can,Guo, Zhenzhen,Shen, Yan,Liu, Fang,Ma, Ruixin,Ma, Shutao
p. 506 - 515
(2015/10/06)

Synthesis of 2-(hetero)aryl-5-(trimethylsilylethynyl)oxazoles from (hetero)arylacrylic acids
A three-step method for the synthesis of 2-(hetero)aryl-5-(trimethylsilylethynyl)oxazoles is described. Easily accessible bis(trimethylsilyl)acetylene and acrylic acid derivatives are used as starting materials for the preparation of mono- and disubstituted 5-(trimethylsilyl)pent-1-en-4-yn-3-ones. Oxidative phthalimidoaziridination of these enynones provides the key 2-acyl-1-phthalimidoaziridines that are further utilized in the thermal expansion of the three-membered ring to furnish the target functionalizable oxazoles.
Pankova, Alena S.,Stukalov, Alexander Yu.,Kuznetsov, Mikhail A.
p. 1826 - 1829
(2015/04/27)

New synthesis method for sultone derivatives: Synthesis, crystal structure and biological evaluation of S-CA
There has been no remarkable progress in the synthesis of sultones in recent years. To facilitate more detailed studies of this functional group, we found a new method to synthesize the sulfonic acid lactone derivatives and finish its ring-closing reactio
Li, Bi,Yan, Wenqiang,Zhang, Chenze,Zhang, Yuzhong,Liang, Miao,Chu, Fuhao,Gong, Yan,Xu, Bing,Wang, Penglong,Lei, Haimin
p. 4307 - 4318
(2015/05/13)

Semisynthetic hybrids of boswellic acids: A novel class of potential anti-inflammatory and anti-arthritic agents
A series of hybrid molecules 7-13 of boswellic acid (BA)/11-keto-β-boswellic acid (KBA) 1/2 with well-known anti-inflammatory drugs (i.e. aspirin, naproxen, ibuprofen and cinnamic acid) have been synthesized and evaluated for their anti-inflammatory and a
Chaturvedi, Devdutt,Dwivedi, Parmesh Kumar,Chaturvedi, Amit K.,Mishra, Nisha,Siddiqui,Mishra, Vorenda
p. 2799 - 2812
(2015/02/19)

Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals
Cinnamides ArCHCHCONRR′ in reactions with arenes Ar′H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give CC bond hydroarylation products ArAr′CHCH2CONRR′ in yields of 63-98%. Reduction (LiAlH4/Et2O) of carbonyl group in the latter results in the formation of 3,3-diarylpropylamines ArAr′CHCH2CH2NRR′, valuable drugs. The reaction intermediates, superelectrophilic dications ArC+H-CH2C(OH+)NRR′, have been characterized by DFT calculations in terms of global electrophilicity index, natural charges, and atomic orbitals contributions.
Zakusilo, Dmitry N.,Ryabukhin, Dmitry S.,Boyarskaya, Irina A.,Yuzikhin, Oleg S.,Vasilyev, Aleksander V.
p. 102 - 108
(2015/02/02)

UV light-mediated difunctionalization of alkenes through aroyl radical addition/1,4-/1,2-Aryl shift cascade reactions
UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.
Zheng, Lewei,Huang, Hongli,Yang, Chao,Xia, Wujiong
supporting information
p. 1034 - 1037
(2015/03/30)