- Design, docking, synthesis, and characterization of novel N'(2-phenoxyacetyl) nicotinohydrazide and N'(2-phenoxyacetyl)isonicotinohydrazide derivatives as anti-inflammatory and analgesic agents
-
Inflammation is the complex biological response of vascular tissues, which is partly determined by prostaglandins (PLA2). The cyclooxygenase (COX) enzyme exists in two isoforms: COX-1 and COX-2 and by the action of this, the PGs are produced. Besides, nonsteroidal anti-inflammatory drugs (NSAIDs) are therapeutic agents useful in the treatment of inflammation. Encouraged by this, the new derivatives of N'(2-phenoxyacetyl)nicotinohydrazide 9(a-e) and N'(2-phenoxyacetyl)isonicotinohydrazide 10(a-e) were designed, synthesized, characterized, and identified as remarkable anti-inflammatory and analgesic agents. These compounds were prepared in a series of steps starting with different phenol derivatives. Among the series, compound (10e) showed the highest IC50 value for COX-1 inhibition, whereas compounds (9e) and (10e) exhibited the highest COX-2SI. Further, molecular Docking Studies have been performed for the potent compound to check the three-dimensional geometrical view of the ligand binding to the targeted enzymes.
- Al-Ostoot, Fares Hezam,Khanum, Shaukath Ara,M, Pallavi H,Vivek, Hamse Kameshwar
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- Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment
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Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.
- Chai, Jianqi,Chen, Min,Jin, Fei,Kong, Xiangyi,Wang, Xiaobin,Xue, Wei,Yang, Chunlong
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- Design, synthesis, in vitro and in silico studies of some novel triazoles as anticancer agents for breast cancer
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Against the increasing incidence of breast cancer in postmenopausal women in recent years, a few clinically approved inhibitors and their side-effect profiles indicate the need for the development of new aromatase inhibitors. In this study, carried out to develop a new aromatase inhibitor, the triazole ring system was preferred because of its known activity in the field. The triazole ring, which is in the structure of the most commonly used aromatase inhibitors such as anastrazole and letrazole, was synthesized from the thiourea residue. Inhibitor structures were elucidated using the 1H-NMR, 13C-NMR, 2D-NMR, and HRMS spectroscopic methods. A cytotoxicity (MTT) test was performed to determine the anticancer activity of the compounds on breast (MCF7) carcinoma cell type. In addition, to determine selectivity of their action, the final compounds were screened against a healthy NIH3T3 cell line (mouse embryonic fibroblast cells). In terms of the MTT assay, it was observed that the calculated IC50 values of compound 5e for the NIH3T3 cell line were found to be higher than for the MCF7 cell lines. Considering the viability results, it was found that the selected compound 5e showed a favorable safety profile and that it has anticancer activities. It was determined by in vitro studies that compound 5e showed inhibition potential on the aromatase enzyme with an IC50 = 0.028 μM value. The docking study of compound 5e revealed that there is a strong interaction between the active sites of the human aromatase enzyme and the analyzed compound.
- ?zkay, Yusuf,Ilg?n, Sinem,Kaplanc?kl?, Zafer As?m,Levent, Serkan,Osmaniye, Derya,Sa?l?k, Begüm Nurpelin
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- Design, synthesis and molecular modelling of phenoxyacetohydrazide derivatives as Staphylococcus aureus MurD inhibitors
-
In the present work we synthesized a new series of phenoxyacetohydrazide functional compounds 4a-k and characterized by spectral data. Synthesized compounds were screened in vitro for their antibacterial activity. Compounds 4a, 4j and 4k exhibited inhibitory activity against S. aureus NCIM 5022 with MIC value of 64?μg/ml These compounds also exhibited activity against methicillin resistant S. aureus ATCC 43300 with MIC of 128?μg/ml. Among all the tested compounds 4c and 4j showed highest activity, respectively against B. subtilis NCIM 2545 and K. pneumoniae NCIM 2706. Only one compound i.e. 4d showed activity against another Gram-negative bacteria P. aeruginosa NCIM 2036 with MIC value of 64?μg/ml. Among three tested compounds, 4k exhibited highest inhibitory activity against S. aureus MurD enzyme with IC50 value of 35.80?μM. Further binding interactions of 4a-k with the modelled S. aureus MurD catalytic pocket residues is investigated with the extra-precision molecular docking and binding free energy calculation by MM-GBSA approach. The van der Waals energy term was observed to be the driving force for binding. Further, 50?ns molecular dynamics simulations were performed to validate the stabilities of 4j- and 4k-modelled S. aureus MurD. Graphic abstract: [Figure not available: see fulltext.]
- Jupudi, Srikanth,Azam, Mohammed Afzal,Wadhwani, Ashish
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p. 1221 - 1235
(2020/10/09)
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- Synthesis method of substituted phenoxyacetate compound
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The invention discloses a synthesis method of a substituted phenoxyacetate compound, relates to a synthesis method of a compound and aims to solve the problems that during current preparation of the substituted phenoxyacetate compound by a condensation method, a large amount of organic agent is consumed, substituted phenol is unlikely to react completely, the content of free phenol in three wastesis high and a very high environmental risk exists. According to the synthesis method, after the substituted phenol is mixed with haloacetate, a condensation reaction is performed in a potassium fluoride system condensing agent under the synergistic catalysis of a phase transfer catalyst and a halogenated hydrocarbon activator to obtain a substituted phenoxyacetic acid compound. The synthesis method is applied to the field of compound synthesis.
- -
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Paragraph 0047-0049; 0083-0085
(2019/08/01)
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- The synthesis and evaluation of phenoxyacylhydroxamic acids as potential agents for Helicobacter pylori infections
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Two series of ω-phenoxy contained acylhydroxamic acids as novel urease inhibitors were designed and synthesized. Biological activity evaluations revealed that ω-phenoxypropinoylhydroxamic acids were more active than phenoxyacetohydroxamic acids. Out of these compounds, 3-(3,4-dichlorophenoxy)propionylhydroxamic acid c24 showed significant potency against urease in both cell free extract (IC50 = 0.061 ± 0.003 μM) and intact cell (IC50 = 0.89 ± 0.05 μM), being over 450- and 120-fold more potent than the clinically prescribed urease inhibitor AHA, repectively. Non-linear fitting of experimental data (V-[S]) suggested a mixed-type inhibition mechanism and a dual site binding mode of these compounds.
- Ni, Wei-Wei,Liu, Qi,Ren, Shen-Zhen,Li, Wei-Yi,Yi, Li-Li,Jing, Heng,Sheng, Li-Xin,Wan, Qin,Zhong, Ping-Fu,Fang, Hai-Lian,Ouyang, Hui,Xiao, Zhu-Ping,Zhu, Hai-Liang
-
supporting information
p. 4145 - 4152
(2018/07/13)
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- Preparation method for 2,4-dichlorophenol, and preparation method for 2,4-dichlorophenolate
-
The invention provides a preparation method for 2,4-dichlorophenol. The preparation method comprises the following steps: S) adding phenol, a promoter and sulfuryl chloride into an organic solvent andcarrying out chlorination under low temperature conditions to obtain 2,4-dichlorophenol, wherein the promoter is one or more selected from the group consisting of dimethyl sulfide, phenyl sulfide andisopropyl ether. Compared with the prior art, the preparation method provided by the invention has the advantage that selectivity is improved due to the reaction under low temperature conditions; andthe promoter is added at the same time to ensure a reaction rate.
- -
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Paragraph 0043; 0045; 0046; 0047; 0048; 0050
(2018/09/08)
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- Preparation method for 2,4-dichlorophenoxyacetic acid
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The invention provides a preparation method for 2,4-dichlorophenoxyacetic acid, belonging to the technical field of organic synthesis. The preparation method comprises the following steps: a) reactinghalogenated acetate with 2,4-dichlorophenolate in the presence of a phase-transfer catalyst so as to obtain 2,4-dichlorophenoxyacetate; and b) hydrolyzing 2,4-dichlorophenoxyacetate so as to obtain 2,4-dichlorophenoxyacetic acid. According to the invention, oil-phase halogenated acetate reacts with 2,4-dichlorophenolate under the action of the phase-transfer catalyst to prepare 2,4-dichlorophenoxyacetate, and then 2,4-dichlorophenoxyacetate is hydrolyzed to obtain 2,4-dichlorophenoxyacetic acid and corresponding alcohols. Under the action of the phase-transfer catalyst, few hydrolysis by-products are produced during a reaction, fast reaction speed and high conversion rate and yield are obtained, and the amount of produced waste water is low; so industrial application of the preparation method can be easily implemented.
- -
-
Paragraph 0047; 0049; 0050
(2018/09/08)
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- Preparation method for 2,4-dichlorophenoxyacetic acid
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The invention provides a preparation method for 2,4-dichlorophenoxyacetic acid, belonging to the technical field of organic synthesis. The preparation method comprises the following steps: a) reactinghalogenated acetate with an anhydrous 2,4-dichlorophenolate solid so as to obtain 2,4-dichlorophenoxyacetate; and b) hydrolyzing 2,4-dichlorophenoxyacetate so as to obtain 2,4-dichlorophenoxyacetic acid. According to the invention, the anhydrous 2,4-dichlorophenolate solid reacts with halogenated acetate to prepare 2,4-dichlorophenoxyacetate, and then 2,4-dichlorophenoxyacetate is hydrolyzed to obtain 2,4-dichlorophenoxyacetic acid and corresponding alcohols. The mass transfer effect of a solid-liquid reaction in the invention is good; few hydrolysis by-products are produced during the reaction; fast reaction speed and high conversion rate and yield are obtained; the amount of produced waste water is low; so industrial application of the preparation method can be easily implemented.
- -
-
Paragraph 0046; 0048; 0049
(2018/09/08)
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- Synthesis and cytotoxicity evaluation of [(2,4-dichlorophenoxy)methyl]-5-aryl-1,3,4-oxadiazole/4H-1,2,4-triazole analogues
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We report herein the synthesis, characterization, and cytotoxicity evaluations of some newer oxadiazole and triazole analogues (5a-j). The cytotoxicity of all the title compounds were evaluated as per the National Cancer Institute protocol in a one-dose assay (10M) on nine different panels of 59 cancer cell lines. 2-f5-[(2,4-Dichlorophenoxy)methyl]-1,3,4-oxadiazol-2-ylgphenol (5e) showed the maximum cytotoxicity among the series of ten compounds. The cytotoxicity of 5e was comparable to that of the standard anticancer drug, 5-fluorouracil, and better than that of imatinib. The structure activity relationship was also discussed.
- Ahsan, Mohamed Jawed
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p. 1334 - 1343
(2018/10/23)
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- Preparation method of 2,4-dichlorophenoxyacetic ester
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The invention provides a preparation method of 2,4-dichlorophenoxyacetic ester, wherein the preparation method includes the following steps: S1) carrying out a reaction of phenol and methyl chloroacetate under alkaline conditions to obtain methyl phenoxyacetate; S2) carrying out selective chlorination reaction of methyl phenoxyacetate with a chlorinating agent under the action of a catalyst A anda catalyst B to obtain 2,4-methyl dichlorophenoxyacetate, wherein the catalyst A is Lewis acid, and the catalyst B is C5-22 thioethers, thiazoles, isothiazoles and thiophenes or halogenated derivatives thereof; and S3) carrying out transesterification reaction of 2,4-methyl dichlorophenoxyacetate and alcohol under the action of a catalyst, to obtain 2,4-dichlorophenoxyacetic ester, wherein the alcohol is C2-20 alcohol. The selective chlorination reaction is carried out with methyl phenoxyacetate as a raw material, the selectivity of the reaction is improved, the loss of effective components isavoided, the yield of the effective components is greatly improved, and the three-waste treatment capacity, the three-waste treatment difficulty and the treatment cost are reduced.
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-
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- Preparation method of 2,4-dichlorophenoxyacetic acid and salt thereof
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The invention provides a preparation method of 2,4-dichlorophenoxyacetic acid and a salt thereof, wherein the preparation method includes the following steps: S1) carrying out a reaction of phenol andchloracetic ester under alkaline conditions to obtain phenoxyacetic ester; S2) carrying out selective chlorination reaction of the phenoxyacetic ester with a chlorinating agent under the action of acatalyst A and a catalyst B to obtain 2,4-dichlorophenoxyacetic ester, wherein the catalyst A is Lewis acid, and the catalyst B is C5-22 thioethers, thiazoles, isothiazoles and thiophenes or halogenated derivatives thereof; and S3) carrying out hydrolysis reaction of 2,4-dichlorophenoxyacetic ester under acidic conditions to obtain 2,4-dichlorophenoxyacetic acid; or after 2,4-dichlorophenoxyaceticester is obtained, carrying out an alkaline hydrolysis reaction with an alkaline compound to obtain 2,4-dichlorophenoxyacetate. The production and use of 2,4-dichlorophenol with unpleasant odor are avoided, the production of dioxins is eliminated, the yield of products is improved, and the output of three wastes is greatly reduced.
- -
-
Paragraph 0103; 0105
(2019/01/06)
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- Preparation method of phenoxycarboxylic acid choline salt
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The invention provides a preparation method of a phenoxycarboxylic acid choline salt, wherein the preparation method includes the steps: S1, carrying out condensation reaction of phenol or o-cresol with chlorocarboxylic ester in the presence of alkaline substances to obtain phenoxycarboxylic ester; S2, carrying out selective chlorination of the phenoxycarboxylic ester with a chlorinating agent inthe presence of a first catalyst and a second catalyst to obtain chlorobenzoxycarboxylic ester; and S3, after reaction of trimethylamine with ethylene oxide, adding the chlorophenoxycarboxylic acid ester, and carrying out alkaline hydrolysis reaction to obtain the phenoxycarboxylic acid choline salt. Compared with a conventional synthesis technology, the preparation method effectively avoids the production and use of chlorophenols with unpleasant odor, radically eliminates the production of highly toxic dioxins, and greatly improves the product quality and the operation environment of the production site; with phenol as the raw material, through condensation, selective chlorination and alkaline hydrolysis, the high-quality phenoxycarboxylic acid choline salt is obtained, the loss of effective ingredients is effectively avoided and the yield of the product is increased.
- -
-
Paragraph 0075; 0077
(2019/01/08)
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- A method for preparing 2, 4 - dichlorophenoxyacetic acid (by machine translation)
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The invention provides a 2, 4 - dichlorophenoxyacetic acid preparation method, comprises the following steps: A) halogenated acetate with 2, 4 - dichlorophen salt reaction, to obtain 2, 4 - dichlorophenoxy ester; B) 2, 4 - dichlorophenoxy ester under the effects of catalyst hydrolysis reaction, to obtain 2, 4 - dichloro acid; said catalyst is selected from a polyether, a crown ether, quaternary ammonium salt, tertiary amine, [...], pyridine, titanate, inorganic acid, in organic acid one or more. The invention by halogenated acetate with 2, 4 - dichlorophen salt obtained by reaction of 2, 4 - dichlorophenoxy ester, and then in particular under the action of catalyst by hydrolysis reaction of the 2, 4 - dichloro acid. The invention specific reaction line combined with a specific catalyst such that the final preparation to obtain 2, 4 - dichlorophenoxyacetic acid purity and yield is relatively high, few by-products, the reaction route is simple, and is favorable for application. (by machine translation)
- -
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Paragraph 0048; 0049
(2018/09/08)
-
- Preparation method for 2,4-dichlorophenoxyacetic acid
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The invention provides a preparation method for 2,4-dichlorophenoxyacetic acid. The preparation method comprises the following steps: A) reacting C2 or above-C2 alcohol with halogenated acetic acid soas to obtain halogenated acetate; B) reacting halogenated acetic acid with 2,4-dichlorophenolate so as to obtain 2,4-dichlorophenoxyacetate; and C) hydrolyzing 2,4-dichlorophenoxyacetate so as to obtain 2,4-dichlorophenoxyacetic acid. According to the invention, C2 or above-C2 alcohol reacts with halogenated acetic acid to obtain a halogenated acetate intermediate, the intermediate has good stability, few reaction by-products are produced, and high yield is realized; then the intermediate further reacts with 2,4-dichlorophenolate to obtain 2,4-dichlorophenoxyacetate; and finally, 2,4-dichlorophenoxyacetate is hydrolyzed to obtain 2,4-dichlorophenoxyacetic acid. Through a specific reaction route of the invention, the finally prepared 2,4-dichlorophenoxyacetic acid has high purity and yield, few by-products are produced, the reaction route is simple, and the application of the preparation method is facilitated.
- -
-
Paragraph 0060; 0061
(2018/09/08)
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- A method for preparing 2, 4 - dichlorophenoxyacetic acid (by machine translation)
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The invention provides a 2, 4 - dichlorophenoxyacetic acid preparation method, comprising: A) a halogenated acetic acid with the monoester should be halogenated acetate; phenol with alkali reaction to obtain the phenoxide; B) halogenated acetate and phenol salt reaction to obtain the phenoxyacetic acid ester; C) phenoxyacetic acid ester under the effects of catalyst chloride to obtain 2, 4 - dichlorophenoxy ester; said catalyst selected from iron trichloride, aluminum trichloride, boron trifluoride, five [...], trifluoromethyl sulfonate, aluminum oxide, ferric oxide, boron trioxide, niobium pentoxide, diphenyl ether, diphenyl sulfide, benzoin two sulfide, dimethyl sulfide and dimethyl sulfide in one or several of the D) 2, 4 - dichlorophenoxy ester hydrolysis to obtain 2, 4 - dichloro acid. This invention adopts the specific reaction routes and chlorinated using a specific catalyst, good reaction selectivity, few by-products, high yield. (by machine translation)
- -
-
Paragraph 0051; 0052
(2018/09/08)
-
- Preparation method and application of composition of 2,4-dichlorophenoxyacetic acid and 2,4-dichlorophenoxyacetate
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The invention provides a preparation method for a composition of 2,4-dichlorophenoxyacetic acid and 2,4-dichlorophenoxyacetate. The preparation method comprises the following steps: reacting halogenated acetate with 2,4-dichlorophenate so as to obtain 2,4-dichlorophenoxyacetate; and directionally hydrolyzing 2,4-dichlorophenoxyacetate prepared in the previous step to obtain the composition of 2,4-dichlorophenoxyacetic acid and 2,4-dichlorophenoxyacetate. According to the invention, a process route is adjusted and creative improvement is made from the foundation; halogenated acetate reacts with2,4-dichlorophenate so as to prepare 2,4-dichlorophenoxyacetate, and directional hydrolysis is carried out so as to obtain the composition of 2,4-dichlorophenoxyacetic acid and 2,4-dichlorophenoxyacetate. The composition of 2,4-dichlorophenoxyacetic acid and 2,4-dichlorophenoxyacetate of the invention has excellent quality, high stability and good drug effect.
- -
-
Paragraph 0093; 0094
(2018/09/08)
-
- Synthesis and Herbicidal Activity of Some Novel Pyrazole Derivatives
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Some novel pyrazole derivatives were designed and synthesized through multi-step reactions from substituted phenol as starting material. Their structures were confirmed by 1H NMR, FTIR, MS and elemental analysis. All these compounds were evaluated their herbicidal activity. The preliminary bioassay results indicated that some of title compounds displayed moderate herbicidal activity at 200 μg/mL. Among them, compounds 4-chloro-N'-(2-(2,5-dimethyl-phenoxy) acetyl)-3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-N'-(2-(2,4-dichlorophenoxy)acetyl)- 3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-3-ethyl-1-methyl-N'-(2-(m-tolyloxy) acetyl)-1H-pyrazole-5-carbohydrazide and 4-chloro-3-ethyl-1-methyl-N'-(2-(3-nitrophenoxy)acetyl)- 1H-pyrazole-5-car-bohydrazide possessed 95%, 100%, 95% and 95% inhibition against Brassica campestris respectively. In the further bioassay, the compound 6l exhibited excellent herbicidal activity either monocotyledon or dicotyledon plant at 150 g/ha.
- He, Hai-Qin,Liu, Xing-Hai,Weng, Jian-Quan,Tan, Cheng-Xia
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p. 195 - 200
(2017/07/22)
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- Novel 2,4-dichlorophenoxy acetic acid substituted thiazolidin-4-ones as anti-inflammatory agents: Design, synthesis and biological screening
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A library of fourteen 2-imino-4-thiazolidinone derivatives (1a-1n) has been synthesized and evaluated for in vivo anti-inflammatory activity and effect on ex-vivo COX-2 and TNF–α expression. Compounds 1k (5-(2,4-dichloro-phenooxy)-acetic acid (3-benzyl-4-oxo-thiazolidin-2-ylidene)-hydrazide) and 1m (5-(2,4-dichloro-phenooxy)-acetic acid (3-cyclohexyl-4-oxo-thiazolidin-2-ylidene)-hydrazide) exhibited in vivo inhibition of 81.14% and 78.80% respectively after 5 h in comparison to indomethacin which showed 76.36% inhibition of inflammation without causing any damage to the stomach. Compound 1k showed a reduction of 68.32% in the level of COX-2 as compared to the indomethacin which exhibited 66.23% inhibition of COX-2. The selectivity index of compound 1k was found to be 29.00 in comparison to indomethacin showing selectivity index of 0.476. Compounds 1k and 1m were also found to significantly suppress TNF-α concentration to 70.10% and 68.43% in comparison to indomethacin which exhibited 66.45% suppression.
- Ali, Yakub,Alam, Mohammad Sarwar,Hamid, Hinna,Husain, Asif,Dhulap, Abhijeet,Bano, Sameena,Kharbanda, Chetna
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supporting information
p. 1017 - 1025
(2017/09/30)
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- Synthesis and biological activity of 1-(Substituted phenoxyacetoxy)- 1-(pyridin-2-yl or thien-2-yl)methylphosphonates
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A series of novel O,O-dimethyl 1-(substituted phenoxyacetoxy)-1-(pyridin-2-yl or thien-2-yl)methylphosphonates 6a-n and 7a-d were synthesized. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 6a, 6c, 6l, 6m, and 7d possess 90-100% inhibition against most of the tested plants at the dosage of 1500 g ai/ha, whereas the title compounds 6b, 6g-h and 6n possess 92-100% inhibition against Fusarium oxysporum, Phyricularia grisea, Botrytis cinereapers, Gibberella zeae, Sclerotinia sclerotiorum, and Cercospora beticola at the concentration of 50mg/L.
- Wang, Tao,Wang, Wei,Peng, Hao,He, Hongwu
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p. 173 - 179
(2015/01/30)
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- Radical decarboxylative fluorination of aryloxyacetic acids using N-fluorobenzenesulfonimide and a photosensitizer
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Fluorinated methoxy arenes are emerging as important motifs in both agrochemicals and pharmaceuticals. A novel technique for the synthesis of monofluoromethoxy arenes through the direct fluorodecarboxylation of carboxylic acids was developed that uses photosensitizers and N-fluorobenzenesulfonimide (NFSI). Utilization of the oxidatively mild fluorine transfer agent NFSI enabled the synthesis of fluoromethyl ethers that were previously inaccessible with decarboxylative fluorinations performed with Selectfluor. Mechanistic studies are consistent with the photosensitizer effecting oxidation of the aryloxyacetic acid.
- Leung, Joe C. T.,Sammis, Glenn M.
-
supporting information
p. 2197 - 2204
(2015/04/14)
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- Anthelmintic evaluation of some novel synthesized 1,2,4-triazole moiety clubbed with benzimidazole ring
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A series of N-[3-{(1H-benzo[d]imidazol-2-ylthio) methyl}-5-mercapto-4H-1,2, 4-triazol-4-yl]-2-substituted phenoxy acetamide 6(a-g) were synthesized by the mixture of the compound of potassium 2-(2-(1H-benzo[d]imidazol-2-ylthio) acetyl) hydrazinecarbodithioate (4) and arytoxy acid hydrazide (5) in presence of hydrochloric acid. The predicted structures of the synthesized compounds were confirmed by different spectral analysis studies. The title compounds 6(a-g) were screened for anthelmintic activity against Pheretima posthumous. The entire compounds were exhibited good anthelmintic activity when compared with standard drugs such as Albendazole and Piperazine.
- Kumar, P. Sudhir,Sahoo
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p. 211 - 217
(2014/06/23)
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- Aggrecanase-2 inhibitors based on the acylthiosemicarbazide zinc-binding group
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Osteoarthritis is a disabling disease characterized by the articular cartilage breakdown. Aggrecanases are potential therapeutic targets for the treatment of this pathology. At the starting point of this project, an acylthiosemicarbazide was discovered to inhibit aggrecanase-2. The acylthiosemicarbazide Zn binding group is also a convenient linker for library synthesis. A focused library of 920 analogs was thus prepared and screened to establish structure-activity relationships. The modification of the acylthiosemicarbazide was also explored. This strategy combining library design and discrete compounds synthesis yielded inhibitor 35, that is highly selective for aggrecanases over a panel of metalloproteases and inhibits the degradation of native fully glycosylated aggrecan. A docking study generated binding conformations explaining the structure-activity relationships.
- Maingot, Lucie,Elbakali, Jamal,Dumont, Julie,Bosc, Damien,Cousaert, Nicolas,Urban, Agathe,Deglane, Gaelle,Villoutreix, Bruno,Nagase, Hideaki,Sperandio, Olivier,Leroux, Florence,Deprez, Benoit,Deprez-Poulain, Rebecca
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p. 244 - 261
(2013/10/01)
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- Design, synthesis, biological activities and 3D-QSAR of new N,N′-diacylhydrazines containing 2,4-dichlorophenoxy moieties
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A series of new N,N′-diacylhydrazine derivatives were designed and synthesized. Their structures were verified by 1H-NMR, MS and elemental analysis. The herbicidal activities and plant growth regulating activity of these N,N′-diacylhydrazines were evaluated. The herbicidal activity results showed that most of these N,N′-diacyl-hydrazines showed excellent in vivo activities against Echinochloa crus-galli, Digitaria sanguinalis, Brassica napus, Amaranthus retroflerus. Most of them exhibited higher herbicidal activities against dicotyledonous weeds than monocotyledonous weeds. To further investigate the structure-activity relationship, comparative molecular field analysis (CoMFA) was performed on the basis of herbicidal activity data. Both the steric and electronic field distributions of CoMFA are in good agreement in this work.
- Sun, Guo-Xiang,Sun, Zhao-Hui,Yang, Ming-Yan,Liu, Xing-Hai,Ma, Yi,Wei, Yun-Yang
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p. 14876 - 14891
(2014/01/17)
-
- Discovery of amide based fibrates as possible antidyslipidemic and antioxidant agents
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A novel series of amide based fibrates were synthesized and evaluated for antidyslipidemic activity in triton induced hyperlipidemic rats. Interestingly, the compound 13 produced striking reduction in serum levels of total cholesterol (TC), phospholipids (PL) and triglycerides (TG). In addition, it exhibited improved lipoprotein lipase activity and found to possess moderate radical scavenging potential. The results of the above studies shows that the compounds synthesized on fibrate based pharmacophores might result in identification of new lead for dyslipidemia.
- Sashidhara, Koneni V.,Palnati, Gopala Reddy,Dodda, Ranga Prasad,Sonkar, Ravi,Khanna,Bhatia, Gitika
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p. 302 - 310
(2013/01/15)
-
- Synthesis and biological activity of α-oxo-2-pyridyl methyl phosphinates
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In an attempt to discover novel compounds with high activity and low toxicity, a series of new O,O-dimethyl-α-(substituted phenoxyacetoxy)-2- pyridyl methyl phosphinates, 5a-5h, have been designed and synthesized by the reaction of substituted phenoxyacetic chloride with 1-hydroxy-2-pyridyl methyl phosphinate, The structures of all new compounds were characterized by elementary analysis, IR, 1H NMR, and MS spectroscopies. The results of preliminary bioassay indicate that most of the target compounds have excellent inhibitory activities on barnyard grass and rape. Copyright Taylor & Francis Group, LLC.
- Wang, Tao,He, Hong Wu
-
scheme or table
p. 1884 - 1891
(2009/09/06)
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- THIADIAZOLE DERIVATIVES, INHIBITORS OF STEAROYL-COA DESATURASE
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The present invention relates to substituted thiadiazole compounds of the formula (I) and pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds for modulating SCD activity.
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Page/Page column 43
(2008/12/07)
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- An efficient synthesis of aryloxyacetic acid and arylthioacetic acid esters
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The esterification of the aryloxyacetic acid and arylthioacetic acid catalysed by silica sulfuric acid results aryloxyacetic acid and arylthioacetic acid ester in 83-94% yields respectively under mild reaction conditions.
- Li, Ji-Tai,Li, Hong-Ya,Li, Hui-Zhang
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p. 416 - 417
(2007/10/03)
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- Bisphosphonates derived from fatty acids are potent growth inhibitors of Trypanosoma cruzi
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We have investigated the effect of a series of bisphosphonates derived from fatty acids against Trypanosoma cruzi proliferation in in vitro assays. Some of these drugs proved to be potent inhibitors against the intracellular form of the parasite exhibiting IC50 values at the low micromolar level. As bisphosphonates are FDA clinically approved for treatment of bone resorption, their potential innocuousness makes them good candidates to control tropical diseases.
- Szajnman, Sergio H.,Bailey, Brian N.,Docampo, Roberto,Rodriguez, Juan B.
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p. 789 - 792
(2007/10/03)
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- Synthesis and quantitative structure - Activity relationships of new 2,5-disubstituted-1,3,4-oxadiazoles
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Fourteen new 2,5-disubstituted-1,3,4-oxadiazoles, namely (i) six 2-[2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropyl]-5-substituted-1,3,4-oxadia zoles and (ii) eight 2-substituted-phenoxymethyl-5-substituted-aryl-1,3,4-oxadiazoles, were synthesized and evaluated for their insect growth regulatory activity against second-instar larvae of armyworm (Pseudaletia separata Walker). Two of these compounds (7 and 8) showed good insecticidal activities, with LC50 values of 14.33 and 15.85 μg/mL, respectively. Steric parameters (e.g., the molecular length d and the ratio of the nonpolar surface area and polar surface area V1/V2) and semiempirical quantum parameters (e.g., the molecular total energy Et and the lowest unoccupied molecular orbital energy ELUMO and so on) of these compounds, as well as those of six other 2,5-disubstituted-1,3,4-oxadiazoles reported, were acquired by the molecular modeling method and the PM3-SCF-MO method, respectively. With the help of the synthons' activity contribution method based on the Free-Wilson approach in its Fujita-Ban variant, quantitative structure-activity relationships were studied by regressing half-lethal concentrations against the above parameters.
- Shi, Wei,Qian, Xuhong,Zhang, Rong,Song, Gonghua
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p. 124 - 130
(2007/10/03)
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- (2,4-Dichlorophenoxy)acetohydrazide
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The title compound, C8H8Cl2N2O2, is an intermediate compound in the synthesis of one of the important 1,2,4-triazoles that possess diverse pharmacological activities.
- Lokanath,Sridhar,Shashidhara Prasad,Nagaraja,Mohan Rao
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p. 669 - 670
(2007/10/03)
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- Mixtures of herbicides and antidotes, (hetero)-aryloxy compounds, their preparation, compositions containing them, and their use
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The invention relates to crop protection agents which comprise an active substance combination of herbicide and safener. The herbicides are selected from the group comprising the ALS inhibitors (ALS=acetolactate synthase) such as sulfonylureas, imidazolines, triazolopyrimidinesulfonamides, pyrimidyloxypyridinecarboxylic acid derivatives and pyrimidyloxybenzoic acid derivatives. The safeners are compounds of the formula I STR1 which are as defined in claim 1, where Z and Y are N or CH, it being possible for H to be replaced by X, X is H, Hal, haloalkyl or -alkoxy, alkyl, alkoxy, alkylthio, NO2, NH2, CN, alkylsulfonyl, A is alkylene or alkenylene, B is carboxyl or a derivative of the carboxyl group. The mixtures are mainly suitable for controlling harmful plants in the crops maize and cereals.
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- Synthesis, Characterization, Spectral and Antifungal Properties of Some 5-Substituted-1,3,4-oxadiazole-2-thiones and Their Mannich Bases
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A series of 5-substituted aryloxymethyl-1,3,4-oxadiazole-2-thione (3a-e) and their Mannich bases 4-8 are synthesized and subjected to fungitoxic screening.The structures of these compounds are established on the basis of elemental analysis 1H-n.m.r. and mass spectral data.The mass spectral fragmentation pathways of these compounds are discussed.
- Holla, B. Shivarama,Kalluraya, Balakrishna,Nath, S. C.
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p. 549 - 557
(2007/10/02)
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- THE SALT-FREE SYNTHESIS OF ARYL ETHERS USING METHYL TRICHLOROACETATE
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Metyl trichloroacetate is an effective reagent for salt-free synthesis of aryl ethers and anisoles from phenols.
- Renga, James M.,Wang, Pen-Chung
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