1734-62-9Relevant academic research and scientific papers
Synthesis and molecular docking based exploration of salicylic acid derivatives
Singh, Navneet,Garg, Geetika
, p. 2377 - 2382 (2018)
In present study, four salicylic acid derivatives viz., 2-acetoxybenzoic acid (2a), 2-(1H-indol-2-yl)benzoic acid (3a), 5-chloro-2-acetoxybenzoic acid (2b) and 5-chloro-2-(1H-indol-2-yl)benzoic acid (3b) were synthesized and studied for molecular docking on 3JUS and 3UPI protein selected from pdb. The studies show that all of the four synthesized compounds were found to be docked. Compound 3a and 3b showed the best ligand pose energy -10.8163 kcal/mol and -11.1354 kcal/mol with docking run: elapsed time 9 s and 12 s, respectively in respect of 3JUS Further, compounds 3a and 3b showed the best ligand pose energy -9.17851 and -9.54722 kcal/mol with docking run: elapsed time 10 and 14 s, respectively in case of 3UPI. Hence, studies showed that 5-chloro-2-(1H-indol-2-yl)benzoic acid (3b) emerged as potent compound which might show diverse nature of biological and therapeutic activity.
Synthesis and antioxidant activities of berberine 9-: O -benzoic acid derivatives
Liu, Yanfei,Long, Shuo,Zhang, Shanshan,Tan, Yifu,Wang, Ting,Wu, Yuwei,Jiang, Ting,Liu, Xiaoqin,Peng, Dongming,Liu, Zhenbao
, p. 17611 - 17621 (2021/05/29)
Although berberine (BBR) shows antioxidant activity, its activity is limited. We synthesized 9-O-benzoic acid berberine derivatives, and their antioxidant activities were screened via ABTS, DPPH, HOSC and FRAP assays. The para-position was modified with halogen elements on the benzoic acid ring, which led to an enhanced antioxidant activity and the substituent on the ortho-position was found to be better than the meta-position. Compounds 8p, 8c, 8d, 8i, 8j, 8l, and especially 8p showed significantly higher antioxidant activities, which could be attributed to the electronic donating groups. All the berberine derivatives possessed proper lipophilicities. In conclusion, compound 8p is a promising antioxidant candidate with remarkable elevated antioxidant activity and moderate lipophilicity.
Synthesis and biological evaluation of novel N-substituted benzamides as anti-migration agents for treatment of osteosarcoma
Chen, Xiaojing,Wang, Guangbao,Mohammed Alsayed, Ali Mohammed,Du, Zongxuan,Lu liu,Ma, Yue,Liu, Peng,Zhang, Qianwen,Chen, Xianxin,Chen, Wenbin,Ye, Faqing,Zheng, Xiaohui,Liu, Zhiguo
, (2021/02/03)
A novel series of novel N-substituted (indole or indazole) benzamides were synthesized, and their anti-tumor properties were evaluated. The majority of tested compounds possessed moderate cytotoxicity, but inspiringly, we verified that active compound 5d presents an astonishing advantage by inhibiting the adhesion, migration, and invasion of osteosarcoma (OS) cells in vitro. Mechanistically, we confirmed 5d inhibited the migration ability of OS cells via the expression of genes related to adhesion, migration, and invasion. This effects of 5d suggest that it can be used as a potential chemotherapeutic drug to some aggressive and/or metastatic cancers, as well as in combination with other clinical anti-cancer drugs. In turn, this could enhance the therapeutic effect or reduce the risk of cell migration.
Chlorinated cobalt alkyne complexes derived from acetylsalicylic acid as new specific antitumor agents
Obermoser, Victoria,Baecker, Daniel,Schuster, Carina,Braun, Valentin,Kircher, Brigitte,Gust, Ronald
supporting information, p. 4341 - 4351 (2018/03/26)
[(Prop-2-ynyl)-2-acetoxybenzoate]dicobalthexacarbonyl (Co-ASS), an organometallic derivative of the irreversible cyclooxygenase-1/2 (COX-1/2) inhibitor acetylsalicylic acid (ASS), demonstrated high growth-inhibitory potential against various tumor cell lines and inhibition of both COX isoenzymes. With the objective of increasing the selectivity for COX-2, we introduced a chlorine substituent in position 3, 4, 5, or 6 of the ASS moiety, respectively. Increased COX-2 selectivity is desirable as this isoenzyme is predominantly related to the development of cancer and abnormal tissue growth. The new compounds were investigated in comprehensive cellular biological assays to identify the impact of the chlorine substitution at the complex on COX-1/2 inhibition, antiproliferative activity, apoptosis, metabolic activity, cell-based COX inhibition, and cellular uptake. Chlorination distinctly reduced the effects at isolated COX-1 (about 25% inhibition at 10 μM; Co-ASS: 82.7%), while those at COX-2 remained almost unchanged (about 65% inhibition at 10 μM; Co-ASS: 78.5%). In cellular systems, with exception of the 6-Cl derivative, all compounds showed notable antitumor activity in COX-1/2 expressing tumor cells (HT-29 (IC50 = 1.5-2.7 μM), MDA-MB-231 (IC50 = 5.2-8.0 μM)), but were distinctly less active in the COX-1/2-negative MCF-7 breast cancer cell line (IC50 = 15.2-22.9 μM). All complexes possess high selectivity for tumor cells, because they did not influence the growth of the non-tumorigenic, human bone marrow stromal cell line HS-5. These findings clearly demonstrate that the interference with the COX-1/2 cascade contributes to the mode of anticancer action of the cobalt alkyne complexes.
Development of 5-nitrothiazole derivatives: Identification of leads against both replicative and latent Mycobacterium tuberculosis
Jeankumar, Variam Ullas,Chandran, Manoj,Samala, Ganesh,Alvala, Mallika,Koushik, Pulla Venkat,Yogeeswari, Perumal,Salina, Elena G.,Sriram, Dharmarajan
, p. 7414 - 7417 (2013/02/22)
Twenty eight 5-nitrothiazole derivatives were synthesized and evaluated for in vitro activities against Mycobacterium tuberculosis (MTB), cytotoxicity against HEK 293T. Among the compounds, 5-nitro-N-(5-nitrothiazol-2-yl)furan-2- carboxamide (20) was found to be the most active compound in vitro with MICs of 5.48 μM against log-phase culture of MTB and also non-toxic up to 100 μM.
Synthesis, biological evaluation and 3D-QSAR studies of 3-keto salicylic acid chalcones and related amides as novel HIV-1 integrase inhibitors
Sharma, Horrick,Patil, Shivaputra,Sanchez, Tino W.,Neamati, Nouri,Schinazi, Raymond F.,Buolamwini, John K.
experimental part, p. 2030 - 2045 (2011/05/05)
HIV-1 integrase is one of the three most important enzymes required for viral replication and is therefore an attractive target for anti retroviral therapy. We herein report the design and synthesis of 3-keto salicylic acid chalcone derivatives as novel HIV-1 integrase inhibitors. The most active compound, 5-bromo-2-hydroxy-3-[3-(2,3,6-trichlorophenyl)acryloyl]benzoic acid (25) was selectively active against integrase strand transfer, with an IC 50 of 3.7 μM. While most of the compounds exhibited strand transfer selectivity, a few were nonselective, such as 5-bromo-3-[3-(4- bromophenyl)acryloyl]-2-hydroxybenzoic acid (15), which was active against both 3′-processing and strand transfer with IC50 values of 11 ± 4 and 5 ± 2 μM, respectively. The compounds also inhibited HIV replication with potencies comparable with their integrase inhibitory potencies. Thus, 5-bromo-2-hydroxy-3-[3-(2,3,6-trichlorophenyl)acryloyl]benzoic acid (25) and 5-bromo-3-[3-(4-bromophenyl)acryloyl]-2-hydroxybenzoic acid (15) inhibited HIV-1 replication with EC50 values of 7.3 and 8.7 μM, respectively. A PHASE pharmacophore hypothesis was developed and validated by 3D-QSAR, which gave a predictive r2 of 0.57 for an external test set of ten compounds. Phamacophore derived molecular alignments were used for CoMFA and CoMSIA 3D-QSAR modeling. CoMSIA afforded the best model with q2 and r2 values of 0.54 and 0.94, respectively. This model predicted all the ten compounds of the test set within 0.56 log units of the actual pIC50 values; and can be used to guide the rational design of more potent novel 3-keto salicylic acid integrase inhibitors.
Influence of impurities on the crystallisation of 5-X-aspirin and 5-X-aspirin anhydride polymorphs (X = Cl, Br, Me)
Solanko, Katarzyna A.,Bond., Andrew D.
experimental part, p. 6991 - 6996 (2012/05/31)
Crystallisation of 5-X-aspirin (X = Cl, Br) by ambient evaporation from organic solvents commonly yields a mixture of polymorphs I and II for X = Cl, but only polymorph I for X = Br. Addition of 5-X-aspirin anhydride (5-20 mol %) leads to sole production
COMPOUNDS AND COMPOSITIONS FOR DELIVERING ACTIVE AGENTS
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Page/Page column 95, (2010/02/14)
Compounds and compositions for the delivery of active agents are provided. Methods of administration and preparation are provided as well.
NF-KB ACTIVATION INHIBITORS
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Page/Page column 120, (2008/06/13)
A medicament having inhibitory activity against NF-κB activation which comprises as an active ingredient a substance selected from the group consisting of a compound represented by the following general formula (I) and a pharmacologically acceptable salt thereof, and a hydrate thereof and a solvate thereof: wherein A represents hydrogen atom or acetyl group, E represents a 2,5-di-substituted or a 3,5-di-substituted phenyl group, or a monocyclic or a fused polycyclic heteroaryl group which may be substituted, provided that the compound wherein said heteroaryl group is 1○ a fused polycyclic heteroaryl group wherein the ring which binds directly to ―CONH― group in the formula (I) is a benzene ring, 2○ unsubstituted thiazol-2-yl group, or 3○ unsubstituted benzothiazol-2-yl group is excluded, ring Z represents an arene which may have one or more substituents in addition to the group represented by formula ―O―A wherein A has the same meaning as that defined above and the group represented by formula -CONH-E wherein E has the same meaning as that defined above, or a heteroarene which may have one or more substituents in addition to the group represented by formula ―O―A wherein A has the same meaning as that defined above and the group represented by formula ― CONH―E wherein E has the same meaning as that defined above.
THERAPEUTIC AGENT FOR CANCER
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Page/Page column 120, (2010/02/11)
A medicament for the prevention and/or treatment of cancers and the like which comprises as an active ingredient a substance selected from the group consisting of a compound represented by the following general formula (I) and a pharmacologically acceptable salt thereof, and a hydrate thereof and a solvate thereof: wherein A represents hydrogen atom or acetyl group, E represents a 2,5-di-substituted or a 3,5-di-substituted phenyl group, or a monocyclic or a fused polycyclic heteroaryl group which may be substituted, provided that the compound wherein said heteroaryl group is 1? a fused polycyclic heteroaryl group wherein the ring which binds directly to ―CONH― group in the formula (I) is a benzene ring, 2? unsubstituted thiazol-2-yl group, or 3? unsubstituted benzothiazol-2-yl group is excluded, ring Z represents an arene which may have one or more substituents in addition to the group represented by formula ―O―A wherein A has the same meaning as that defined above and the group represented by formula ―CONH―E wherein E has the same meaning as that defined above, or a heteroarene which may have one or more substituents in addition to the group represented by formula ―O―A wherein A has the same meaning as that defined above and the group represented by formula ― CONH―E wherein E has the same meaning as that defined above.
