5538-51-2Relevant articles and documents
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.
Diphenylurea derivatives for combating methicillin- and vancomycin-resistant Staphylococcus aureus
Eissa, Ibrahim H.,Mohammad, Haroon,Qassem, Omar A.,Younis, Waleed,Abdelghany, Tamer M.,Elshafeey, Ahmed,Abd Rabo Moustafa, Mahmoud M.,Seleem, Mohamed N.,Mayhoub, Abdelrahman S.
, p. 73 - 85 (2017/03/02)
A new class of diphenylurea was identified as a novel antibacterial scaffold with an antibacterial spectrum that includes highly resistant staphylococcal isolates, namely methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA & VRSA). Starting with a lead compound 3 that carries an aminoguanidine functionality from one side and a n-butyl moiety on the other ring, several analogues were prepared. Considering the pharmacokinetic parameters as a key factor in structural optimization, the structure-activity-relationships (SARs) at the lipophilic side chain were rigorously examined leading to the discovery of the cycloheptyloxyl analogue 21n as a potential drug-candidate. This compound has several notable advantages over vancomycin and linezolid including rapid killing kinetics against MRSA and the ability to target and reduce the burden of MRSA harboring inside immune cells (macrophages). Furthermore, the potent anti-MRSA activity of 21n was confirmed in?vivo using a Caenorhabditis elegans animal model. The present study provides a foundation for further development of diphenylurea compounds as potential therapeutic agents to address the burgeoning challenge of bacterial resistance to antibiotics.
Synthesis and in vitro anticancer activity of novel 2-((3-thioureido) carbonyl)phenyl acetate derivatives
Xiong, Lin,Gao, Ya-Qin,Niu, Chu-E.,Wang, Hong-Bo,Li, Wei-Hong
, p. 132 - 137 (2014/03/21)
Novel simplified Aspirin derivatives were developed, characterized by using IR, 1H NMR, 13C NMR and elementalanalysis techniques and evaluated for anticancer activity in human cell lines. The results revealed that most of the compounds exhibited inhibitory effects of growth of cancer cell lines in vitro against T-acute lymphoblastic leukemia cell lines Molt-4, chronic myclogenous leukemia cell lines K-562, acute myelocytic leukemia cells lines HL-60, human breast cancer cell lines MCF-7, human hepatic carcinoma cell lines HepG-2 and human lung cancer cell lines A-549. It was observed that some of these compounds exhibited significant anticancer activity particularly 5i which had stronger antileukemia activity with IC50 values ranging from 11.12 to 19.25 μmol·L-1 against 3 leukemia cells than control fluorouracil, so some of the compounds may constitute a novel class of anticancer medicines, which deserves further study.
Synthesis and antibacterial activity of acetoxybenzoyl thioureas with aryl and amino acid side Chains
Ngaini, Zainab,Mohd Arif, Maya Asyikin,Hussain, Hasnain,Mei, Er Su,Tang, Donna,Kamaluddin, Dyg Halimatulzahrah Abang
experimental part, p. 1 - 7 (2012/03/27)
A series of acetoxybenzoylthioureas derivatives with aryl and amino acid ester side chains were prepared by reaction of acetoxybenzoyl isothiocyanate, an acyloxy benzyl ester-based derivative of aspirin, with aryl amines or amino-functionalized amino acids with overall yields of 46-73%. The products that display a thiourea segment as a linker showed improved antibacterial properties in comparison with aspirin. The structures of the synthesized compounds were characterized by infra red spectroscopy, 13C nuclear magnetic resonance (NMR), and 1H NMR spectroscopy. The compounds were screened for their antibacterial activity by using gram-negative bacteria (E. coli ATCC 8739). [2-(phenylcarbamothioylcarbamoyl)phenyl] acetate showed the highest antibacterial activity against E. coli compared with other synthesized compounds. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor and Francis Group, LLC.
Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy
He, Jie,Li, Dongdong,Xiong, Kun,Ge, Yongjie,Jin, Hongwei,Zhang, Guozhou,Hong, Mengshi,Tian, Yongliang,Yin, Jin,Zeng, Huihui
, p. 3816 - 3827 (2012/08/27)
Thioredoxin reductase (TrxR) is critical for cellular redox regulation and is involved in tumor proliferation, apoptosis and metastasis. Its C-terminal redox-active center contains a cysteine (Cys497) and a unique selenocysteine (Sec498), which are exposed to solvent and easily accessible. Thus, it is becoming an important target for anticancer drugs. Selective inhibition of TrxR by 1,2-(bis-1,2-benzisoselenazol-3(2H)-one)ethane (4a) prevents proliferation of several cancer cell lines both in vivo and in vitro. Using the structure of 4a as a starting point, a series of novel bis-1,2-benzisoselenazol-3(2H)-ones was designed, prepared and tested to explore the structure-activity relationships (SARs) for this class of inhibitor and to improve their potency. Notably, 1,2-(5,5′-dimethoxybis(1,2-benzisoselenazol-3(2H)-one))ethane (12) was found to be more potent than 4a in both in vitro and in vivo evaluation. Its binding sites were confirmed by biotin-conjugated iodoacetamide assay and a SAR model was generated to guide further structural modification.
ENHANCED TISSUE PENETRATION PRODRUGS
-
Page/Page column 35, (2010/11/25)
The present invention relates to derivatives of carboxy-containing drugs for enhancing tissue penetration and pharmaceutical compositions comprising such derivatives.
New 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, potassium channel activators. IV.
Biagi,Giorgi,Livi,Scartoni,Barili,Calderone,Martinotti
, p. 827 - 834 (2007/10/03)
This paper reports the synthesis of a series of new 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, which have been tested for their activity as possible activators of potassium channels. In rat aortic rings, the 'opened' derivatives 1a-f, intermediates of synthesis, showed vasorelaxing properties, with appreciable values of potency. However, the most remarkable effects were recorded for the 2-hydroxybenzoylbenzotriazoles 3a-f, which showed full vasorelaxing efficacy and high potency values. The introduction of a 2-hydroxybenzyl substituent in the 1 position of the benzotriazole ring (compound 7) strongly decreased the activity, showing the importance of the electron-acceptor carbonyl function. The best compound, 3b, was further investigated, in order to evaluate the possible mechanism of action involved in the vasodilator activity. In the vascular model, different potassium channel blockers inhibited the effects of the compound, and an increase of the levels of membrane depolarisation induced a significant reduction of the recorded responses. Compound 3b was also tested in a model of isolated rat heart, retroperfused through the aorta and submitted to a global ischemia/reperfusion cycle. In such an experimental condition, 3b showed an interesting cardioprotective activity. All the above observations are in agreement with the hypothesis of a mechanism linked to the activation of potassium channels.
STUDIES ON OXYGEN HETEROCYCLES PART-1 : ACID CATALYSED AND PHOTOCHEMICAL REACTIONS OF SOME ARYLDIAZOKETONES
Ghosh, Somnath,Datta, Indira,Chakraborty, Rupak,Das, Tapas Kumar,Sengupta, Judhajit,Sarkar, Dipak Chandra
, p. 1441 - 1446 (2007/10/02)
Trifluoroacetic acid catalysed reaction of 2-methoxyphenyldiazomethylketone (4a), 2-acetoxyphenyldiazomethylketone (4b) and 3-(2-anisyl)-α-diazo-2-propanone (11) leads to the formation of coumaranone (6) and 3-chromanone (12), while 4-(2-anisyl)-α-diazo-2-butanone (16) affords benzo-1-oxepan-3-one (17) and 5-methoxy-2-tetralone (18) in moderate yield.The photochemical decomposition of the said diazoketones (4a, 11 and 16) gave products depending on the length of the side chain present in the substrates.
Process for the obtaining of esters of acetylsalicylic acid and amino alcohols
-
, (2008/06/13)
The present invention relates to a new process for the obtaining of dimethylaminoethyl acetylsalicylate and its salts. It is characterized by the fact that the synthesis of the acid chloride is effected in an aliphatic hydrocarbon in the presence of pyridine as catalyst; after condensation with the dimethylaminoethanol, the product obtained is recovered by crystallization in anhydrous medium. The products obtained can be used in the pharmaceutical industry.
8-Oxa-3-azabicyclo(3.2.1)octane analgesic compositions and method of alleviating pain in animals
-
, (2008/06/13)
Disclosed are compounds, having the following general formula, which are useful as analgesics in living animals. SPC1 Wherein R is a radical selected from the group consisting of aralkyl, aryl, aminoalkyl, arylalkanoyl, heteroaroyl, alkoxy substituted aroyl, alkenyl (C2 to C4), halogen substituted aralkyl, guanadinoalkyl, halogen substituted aroyl, alkyl substituted aroyl, halogen substituted arylalkanoyl, hexahydrobenzoyl, arylalkenoyl, o- or p-alkyl substituted phenylalkanoyl, alkyl substituted naphthylalkanoyl, alkanoyl (C3 to C20), haloalkyl substituted aroyl, alkoxy substituted aralkyl, heteroaralkyl, anilinocarbonyl, adamantanecarbonyl, arylsulfonyl, carboxyl substituted aroyl, hydroxyl substituted aroyl, alkanoyloxy substituted aroyl, arylglyoxylyl, alicyclic, arylene dicarbonyl-8-oxa-3-azabicyclo(3.2.1)octane, alkylene-8-oxa-3-azabicyclo (3.2.1)octane, alkylene dicarbonyl-8-oxa-3-azabicyclo(3.2.1)octane, and the pharmacologically acceptable acid addition salts thereof.
