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Kalaga Mahalakshmi Naidu Rudresh Naik Gajanan Kondapalli Venkata Gowri Chandra Sekhar 《Arabian Journal of Chemistry》2019,12(8):2418-2429
A series of thirty-six novel 5-(2-(4-(benzo[d]isoxazol-3-yl)piperazin-1-yl)acetyl)indolin-2-one and 5-(2-(4-substitutedpiperazin-1-yl)acetyl)indolin-2-one analogues were synthesized, characterized and screened for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain. These compounds exhibited minimum inhibitory concentration between 1.56 and 50 μg/mL. Among these derivatives, compounds 10c, 10d, 10j, 10o and 10v (MIC 6.25 μg/mL) displayed moderate activity, while compounds 10e, 10l, 10q, 10w,10x, 12d, 12e and 12i (MIC 3.12 μg/mL) showed good anti-tubercular activity and compounds 10f, 10k, 10p, 10r, 12f, 12j and 12k (MIC 1.56 μg/mL) exhibited excellent anti-tubercular activity. In addition, MTT assay was accomplished on the active analogues of the series against mouse macrophage (RAW 264.7) cells to evaluate the cytotoxic effect of the newly synthesized compounds and selectivity index of the compounds was determined. 相似文献
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Huang HC Chiou CT Hsiao PC Liaw CC Zhang LJ Chang CL Chen IS Chen WC Lee KH Kuo YH 《Molecules (Basel, Switzerland)》2012,17(2):1837-1851
One new phenylpropanoid, turformosin A (1), and one new triterpene, turformosinic acid (2), together with 16 known compounds, were isolated from the stems of Turpinia formosana Nakai. All structures were elucidated on the basis of spectroscopic analysis, including 1D- and 2D-NMR techniques and MS analysis. Selected isolated compounds were evaluated for in vitro cytotoxicity against four human cancer cell lines and antioxidant scavenging effects on DPPH. (-)-(7'S,8'S)-threo-carolignan X (3) exhibited cytotoxicity against Hep2, WiDr, Daoy, and MCF-7 cell lines with ED(50) values of 3.60, 4.45, 6.07, and 13.7 μg/mL, respectively. Turformosin A (1), (-)-(7'S,8'S)- threo-carolignan X (3), methoxyhydroquinone-4-β-D-glucopyranoside (5), and methoxy-hydroquinone-1-β-D-glucopyranoside (6), exhibited similar anti-oxidative activity. Hep2 cells treated with 10 μg/mL of 3 showed elevation of sub-G1 population (from 20% at 8 h to 60% at 48 h), and activation of caspase-9/caspase-3/PARP cascade. Compound 3 induced intrinsic apoptotic pathway in Hep2 cells with dose and time dependence (10 μg/mL for 8 h). 相似文献
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A series of novel 7-(3-amino-6,7-dihydro-2-methyl-2H-pyrazolo[4,3-c]pyridin- 5(4H)-yl)fluoroquinolone derivatives were designed, synthesized and characterized by 1H-NMR, MS and HRMS. These fluoroquinolones were evaluated for their in vitro antibacterial activity against representative Gram-positive and Gram-negative strains. Results reveal that most of the target compounds exhibit good growth inhibitory potency against methicillin-resistant Staphylococcus epidermidis (MRSE) (MIC: 0.25-4 μg/mL) and Streptococcus pneumoniae (MIC: 0.25-1 μg/mL). In addition, compound 8f is 8-128 fold more potent than the reference drugs gemifloxacin (GM), moxifloxacin (MX), ciprofloxacin (CP) and levofloxacin (LV) against methicillin-resistant Staphylococcus aureus 10-05 and Streptococcus hemolyticus 1002 and 2-64 fold more active against methicillin-sensitive Staphylococcus aureus 10-03 and 10-04. 相似文献
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Refaie M. Kassab Zeinab A. Muhammad Sami A. Al-Hussain Magdi E. A. Zaki Mona H. Ibrahim Amani M. R. Alsaedi Thoraya A. Farghaly 《Journal of heterocyclic chemistry》2024,61(2):217-231
The prevalence of germs that are resistant to many antibiotics is rising rapidly the world over. There is a large group of researchers actively looking for better medicines. Here, we designed two series of hydrazonal and indeno[1,2-b]pyridin-5-one bearing hydrazone and azo-groups to test their antimicrobial activity. Molecular structures of all derivatives were assured based on their spectral data and elemental analyses. Results of the antimicrobial activity of the tested hydrazone and azo compounds showed promising potential for several derivatives. The minimum inhibitory concentrations (MICs) of hydrazones 4a - h and 6a - g displayed good antibacterial reactivities with a range of 3.91–250 μg/mL and moderate antifungal activity with a range of 15.6–500 μg/mL. The most promising hydrazone 4f and azo- 6a compounds demonstrated MIC values against Streptococcus faecalis and Escherichia coli equal to 3.91 and 7.81 μg/mL, respectively. Moreover, azo compound 6a showed MIC value equal to 3.91 μg/mL against Enterobacter cloacae species. Additionally, derivative 4f exhibited a significant inhibitory profile against the E. coli gyrase A enzyme (IC50 = 5.53 μg/mL). On the other hand, compound 6a (IC50 14.05 μg/mL) exhibited the lowest DNA gyrase inhibitory activity as compared to compounds 4f and reference standard drug novobiocin, IC50 5.53 and 1.88 μg/mL, respectively. Pharmacokinetic and pharmacodynamic profiles and molecular docking studies for the two most promising molecules 4f and 6a were computed and revealed that both compounds have good ADME profiles and high binding affinity to DNA gyrase binding site. 相似文献
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Ravi Kumar Reshmi R. Nair Saurabh Sudha Dhiman Jitender Sharma Om Prakash 《Journal of heterocyclic chemistry》2011,48(5):1211-1215
Synthesis of a series of new 4‐substituted‐3‐aryl‐1‐(2,6‐dimethylpyrimidin‐4‐yl)pyrazoles ( 2a , 2b , 2c , 2d , 2e , 2f , 2g , 3a , 3b , 3c , 3d , 3e , 3f , 3g , and 4a , 4b , 4c , 4d , 4e , 4f , 4g ) is described. All the synthesized compounds were evaluated in vitro for their antibacterial activity against two gram‐positive and two gram‐negative bacteria, namely, Bacillus subtilis (MTCC 8509), Bacillus stearothermophilus (MTCC 8508), Escherichia coli (MTCC 51), and Pseudomonas putida (MTCC 121), and their activity was compared with two commercial antibiotics, streptomycin and chloramphenicol. Two compounds, namely, 3‐(4‐anisyl)‐1‐(2,6‐dimethylpyrimidin‐4‐yl)pyrazole‐4‐carboxaldehyde ( 2b ) and 3‐(2‐thienyl)‐1‐(2,6‐dimethyl pyrimidin‐4‐yl)pyrazole‐4‐carboxaldehyde ( 2g ) were found to be equipotent to streptomycin and chloramphenicol against gram‐negative bacteria, E. coli having minimum inhibitory concentration (MIC) value = 4 μg/mL. Compounds 4b and 4d also displayed good activity against E. coli with MIC = 8 μg/mL. J. Heterocyclic Chem., (2011). 相似文献
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Xu W He J He M Han F Chen X Pan Z Wang J Tong M 《Molecules (Basel, Switzerland)》2011,16(11):9129-9141
A series of new sulfone compounds containing 1,3,4-oxadiazole moieties were synthesized. The structures of these compounds were confirmed by spectroscopic data (IR, 1H- and 13C-NMR) and elemental analyses. Antifungal tests indicated that all the title compounds exhibited good antifungal activities against eight kinds of plant pathogenic fungi, and some showed superiority over the commercial fungicide hymexazol. Among them, compounds 5d, 5e, 5f, and 5i showed prominent activity against B. cinerea, with determined EC?? values of 5.21 μg/mL, 8.25 μg/mL, 8.03 μg/mL, and 21.00 μg/mL, respectively. The present work demonstrates that sulfone derivatives such as 5d containing a 1,3,4-oxadiazole moiety can be used as possible lead compounds for the development of potential agrochemicals. 相似文献
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《Tetrahedron》2019,75(25):3463-3471
Six new compounds, named conoideoglucosides A − C and conoideochromanes A − C, together with eight known compounds, including eutypinic acid, 2,2-dimethyl-2H-1-chromene-6-carboxylic acid, (−)-luteoskyrin, (−)-4a-oxyluteoskyrin, chrysophanol, islandicin, catenarin, and (22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol were isolated from the insect fungus Conoideocrella krungchingensis BCC53666. (−)-Luteoskyrin exhibited a broad range of antimicrobial activity such as antimalarial (IC50 0.51 μg/mL), antitubercular (MIC 6.25 μg/mL), antibacterial (both Gram positive; MIC 0.39–1.56 μg/mL and Gram negative; MIC 3.13–12.50 μg/mL), and antifungal (against various plant pathogens; MIC 3.13–50.00 μg/mL) activities, while (−)-4a-oxyluteoskyrin and catenarin showed weaker antibacterial activity. Moreover, eutypinic acid, (−)-luteoskyrin, (−)-4a-oxyluteoskyrin, and catenarin showed cytotoxicity against NCI-H187 cells with IC50 in a range of 0.16–17.99 μg/mL, while eutypinic acid and catenarin had no cytotoxicity against non-cancerous (Vero) cells at maximum tested concentration (50 μg/mL). The complete NMR spectral data and biological activity of the known (−)-4a-oxyluteoskyrin was also reported for the first time. 相似文献
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Phongmaykin J Kumamoto T Ishikawa T Saifah E Suttisri R 《Natural product research》2011,25(17):1621-1628
From the fruits and leaves of Aglaia erythrosperma (Meliaceae), 10 chemical constituents were isolated and identified, i.e. the dammarane triterpenoids cabraleadiol (1), cabraleahydroxylactone (2), ethyl eichlerianoate (3), eichlerialactone (4), aglinin A (5), cabralealactone (6), the aglaialactone 5,6-desmethylenedioxy-5-methoxy-aglalactone (7), the flavagline 4'-demethoxy-3',4'-methylenedioxy-methyl rocaglate (8) and two coumarins: scoparone and scopoletin. Flavagline 8 exhibited antimalarial activity with an IC(50) value of 7.30 μg mL(-1) and was strongly cytotoxic against small cell lung cancer (NCI-H187), epidermoid carcinoma (KB) and breast cancer (BC) cell lines, with IC(50) values of 2.17, 2.10 and 0.11 μg mL(-1), respectively. Aglinin A (5) displayed moderate cytotoxicity against all the three cancer cell lines, whereas ethyl eichlerianoate (3), cabralealactone (6) and the aglaialactone 7 were exclusively cytotoxic to NCI-H187 cell line. Cabraleahydroxylactone (2) showed antiviral activity against herpes simplex virus type-1 with an IC(50) value of 3.20 μg mL(-1), in comparison with the standard acyclovir (IC(50)?= 1.90 μg mL(-1)). When tested for antimycobacterial activity against Mycobacterium tuberculosis H(37)Ra, compounds 1-4 and 6-8 displayed minimum inhibitory concentration in the range of 25-50 μg mL(-1). 相似文献
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PC Esquivel-Ferriño JM Favela-Hernández E Garza-González N Waksman MY Ríos M del Rayo Camacho-Corona 《Molecules (Basel, Switzerland)》2012,17(7):8471-8482
Bioassay guided fractionation of an antimycobacterial extract of Foeniculum vulgare var dulce (Apiaceae) led to the isolation and characterization of 5-hydroxyfurano-coumarin. The chemical structure of this compound was elucidated by 1H and 13C (1D and 2D) Nuclear Magnetic Resonance (NMR) spectroscopy. In addition, the active fractions were analyzed by GC-MS and seventy eight compounds were identified; the major compounds were 1,3-benzenediol, 1-methoxycyclohexene, o-cymene, sorbic acid, 2-hydroxy-3-methyl-2-cyclopenten-1-one, estragole, limonene-10-ol and 3-methyl-2-cyclopenten-1-one. Twenty compounds identified in the active fractions were tested against one sensitive and three MDR strains of Mycobacterium tuberculosis using the Alamar Blue microassay. Compounds that showed some degree of antimycobacterial activity against all strains tested were the following: linoleic acid (MIC 100 μg/mL), oleic acid (MIC 100 μg/mL), 1,3-benzenediol (MIC 100-200 μg/mL), undecanal (MIC 50-200 μg/mL), and 2,4-undecadienal (MIC 25-50 μg/mL), the last being the most active compound. To our knowledge, this is the first report of the presence of 5-hydroxy-furanocoumarin in F. vulgare. 相似文献
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为了寻找具有较好生物活性的吡唑肟醚类衍生物,基于唑螨酯的结构,在吡唑环的4-位引入1,3,4-噁二唑结构,设计合成了15个结构新颖的吡唑肟醚类化合物,它们的结构通过1H NMR、13C NMR、元素分析等手段得到表征.生测研究表明,部分目标化合物在500和100μg/mL浓度下对粘虫(Oriental armyworm)或蚜虫(Aphis medicaginis)都有较好的杀虫效果,其中10a, 10e, 10f和10j在100μg/mL时对粘虫有100%的杀死率, 10g, 10j和10l在100μg/mL时对蚜虫有100%的杀虫活性.另外, 10l在500μg/mL浓度下对朱砂叶螨(Tetranychus cinnabarinus)也具有100%的杀灭效果. 相似文献
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With the aim of discovering a lead compound for pyridine‐based fungicide bearing adamantane moiety, a series of novel O‐alkyl/benzyl‐1‐(adamantan‐1‐yl)‐2‐(pyridin‐3‐yl)ethan‐1‐one oximes were synthesized from 3‐methylpyridine, ethyl (adamantan‐1‐yl)carboxylate, and alkoxyamine or benzoxyamine hydrochloride. The in vitro antifungal activity against four pathogenic fungi was evaluated, and some compounds exhibited good antifungal activity. Compounds 3d and 3f demonstrated strong activity against Sclerotinia sclerotiorum, with EC50 values of 11.25 and 12.87 μg/mL, respectively; 3b , 3c, and 3k had notable activity against Botrytis cinerea, with EC50 values of 12.78, 12.57, and 11.97 μg/mL, respectively. For Rhizoctonia Solani, 3d and 3g showed sufficient activity with EC50 values of 9.66 and 8.90 μg/mL, respectively. In addition, 3d and 3g demonstrated moderate activity against Colletotrichum orbiculare, with EC50 values of 14.32 and 15.83 μg/mL, respectively. 相似文献
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2-甲基间二酚或5-甲基间二酚分别与dl-苹果酸或乙酰乙酸乙酯, 在浓硫酸催化下, 经Peachmann缩合反应得到伞型酮(7-羟基香豆素)类似物5~7. 5~7经甲基化得新化合物5a, 6a和7a; 经Williamson反应, TBAB(四正丁基溴化铵)相转移催化合成了14个新的香豆素类化合物5b~5e, 6b~6f, 7b~7f. 经IR, MS, 1H NMR及元素分析对所有化合物的结构进行了表征. 初步生物活性实验结果表明, 在50 μg/mL浓度下, 化合物6对辣椒疫霉病菌(Phytophythora capsici)抑制率达58.5%, 化合物7c对番茄灰霉病菌(Botrytis cinerea)抑制率为54.0%, 化合物6c对水稻纹枯病菌(Rhizoctonia solani)的抑制率达83.7%. 相似文献
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A series of 1,3-oxazole, 1,3-thiazole, isomeric 1,2,4-oxadiazole, 1,3,4-oxadiazole, and 1,2,3,4-tetrazole heterocycles was synthesized. All the compounds shared as a common feature the presence of a 4-hydroxyphenyl substituent. The structures of the synthesized compounds were confirmed by MS, 1H-NMR, and elemental analysis. In vitro antimicrobial activity for all the newly synthesized compounds at concentrations of 200-25 μg/mL was evaluated against Gram+ve organisms such as methicillin-resistant Staphylococcus aureus (MRSA), Gram-ve organisms such as Escherichia coli (E. coli), and the fungal strain Aspergillus niger (A. niger) by the cup plate method. Ofloxacin and ketoconazole (10 μg/mL) were used as reference standards for antibacterial and antifungal activity, respectively. Compounds 15, 16, and 20 showed notable antibacterial and antifungal activities at higher concentrations (200 μg/mL), whereas 17-19 were found to display significant antibacterial or antifungal activity (25-50 μg/mL) against the Gram+ve, Gram-ve bacteria, or fungal cells used in the present study. 相似文献
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Tashfeen Akhtar Shahid Hameed Najim A. Al‐Masoudi Khalid M. Khan 《Heteroatom Chemistry》2007,18(3):316-322
5‐substituted 4‐(4‐chlorophenyl)‐4H‐1,2,4‐triazol‐3‐thiones 3 and 2‐substituted 5‐(4‐chlorophenylamino)‐1,3,4‐thiadiazoles 4 were prepared from the intermediate thiosemicarbazides 2 under basic and acidic conditions, respectively. The thiosemicarbazides, in turn, were prepared by the reaction of hydrazides 1 with 4‐chlorophenylisothiocyanate in MeOH. Some of the new synthesized compounds were assayed against HIV‐1 and HIV‐2 in MT‐4 cells. All the compounds were inactive except 3f , which showed an EC50 value of 23.9 μg/mL and 9.9 μg/mL against HIV‐1 and HIV‐2 with a therapeutic index of 3 and 7, respectively. It means that compound 3f was cytotoxic to MT‐4 cells at CC50 of 72.7 μg/mL in both strains. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:316–322, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20282 相似文献
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Design,Synthesis, and in vitro Antimicrobial Activity of New Furan/Thiophene‐1,3‐Benzothiazin‐4‐one Hybrids
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This study presents the design, synthesis, spectral analysis, and in vitro antimicrobial evaluation of a new series of furan/thiophene‐1,3‐benzothiazin‐4‐one hybrids ( 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 ). New compounds were obtained by cyclization reaction of N‐substituted furan/thiophene‐2‐carboxamide derivatives ( 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ) with thiosalicylic acid. All synthesized compounds were screened for their in vitro antimicrobial activities using the broth microdilution method. Nine of the synthesized compounds showed good activity against Gram‐positive, Gram‐negative bacteria, and yeasts belonging to Candida spp. (MIC = 7.81–500 μg/mL), especially against Staphylococcus spp. (MIC = 15.62–62.5 μg/ml), Bacillus spp. (MIC = 7.81–62.5 μg/mL), Bordetella bronchiseptica ATCC 4617 (MIC = 62.5–125 μg/mL), and fungistatic activity against Candida spp. (MIC = 62.5–125 μg/mL). 相似文献
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4-[3-(吡啶-4-基)-3-取代苯基丙烯酰]吗啉类化合物的合成及杀菌活性 总被引:1,自引:0,他引:1
为了寻找具有高活性的含吡啶杂环杀菌剂, 以烯酰吗啉为模板化合物, 以异烟酸为起始原料, 通过卤代反应、Friedel-Crafts酰基化反应、Wittig-Horner反应等, 将吡啶-4-基或2-氯吡啶-4-基引入到模板结构中, 设计合成了27个4-[3-(吡啶-4-基)-3-取代苯基丙烯酰]吗啉类化合物, 其结构通过1H NMR和元素分析确证. 对目标化合物的初步杀菌活性测定结果表明, 所有目标化合物对立枯丝核菌(Rhizoctonia solani Kuhn.)和掘氏疫霉菌(Phytophthora drechsler Tucker)均有较强的抑制作用, 其中4-20, 4-21, 4-22化合物对立枯丝核菌的EC50值分别为28.94, 5.27和0.87 μg/mL(对照药剂多菌灵为1.54 μg/mL, 烯酰吗啉为60.95 μg/mL); 对掘氏疫霉菌的EC50值分别为0.33, 0.27和0.09 μg/mL(对照药剂百菌清为20.39 μg/mL, 烯酰吗啉为0.24 μg/mL), 表明该类化合物具有重大的研究开发价值. 相似文献