- Rhodomentosones A and B: Two Pairs of Enantiomeric Phloroglucinol Trimers from Rhodomyrtus tomentosa and Their Asymmetric Biomimetic Synthesis
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Rhodomentosones A and B (1 and 2), two pairs of novel enantiomeric phloroglucinol trimers featuring a unique 6/5/5/6/5/5/6-fused ring system were isolated from Rhodomyrtus tomentosa. Their structures with absolute configurations were elucidated by NMR spe
- Bai, Yang-Ting-Zhi,Deng, Lu-Ming,Hu, Li-Jun,Huang, Xiao-Jun,Jiang, Ren-Wang,Li, Chuang-Chuang,Li, Yao-Lan,Qin, Guan-Qiu,Song, Qiao-Yun,Su, Jun-Cheng,Tang, Wei,Wang, Jie,Wang, Ying,Ye, Wen-Cai
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Read Online
- Friedel-Crafts Alkylation of Acylphloroglucinols Catalyzed by a Fungal Indole Prenyltransferase
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Naturally occurring prenylated acylphloroglucinol derivatives are plant metabolites with diverse biological and pharmacological activities. Prenylation of acylphloroglucinols plays an important role in the formation of these intriguing natural products and is catalyzed in plants by membrane-bound enzymes. In this study, we demonstrate the prenylation of such compounds by a soluble fungal prenyltransferase AnaPT involved in the biosynthesis of prenylated indole alkaloids. The observed activities of AnaPT toward these substrates are much higher than that of a microsomal fraction containing an overproduced prenyltransferase from the plant hop.
- Zhou, Kang,Ludwig, Lena,Li, Shu-Ming
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Read Online
- Polycyclic benzodifuran compound and application thereof as anti-RSV drug
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The invention discloses a polycyclic benzodifuran compound with a formula (I), a preparation method thereof and an application of the polycyclic benzodifuran compound as an anti-respiratory syncytialvirus (RSV) drug. The polycyclic benzodifuran compound d
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Paragraph 0027
(2021/01/04)
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- A greatly improved procedure for the synthesis of an antibiotic-drug candidate 2,4-diacetylphloroglucinol over silica sulphuric acid catalyst: multivariate optimisation and environmental assessment protocol comparison by metrics
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Efforts toward the development of a straightforward greener Gram-scale synthesis of the antibiotic compound 2,4-diacetylphloroglucinol (DAPG) have been developed. This beneficial procedure was accomplished through the Friedel-Crafts acylation of phloroglucinol over inexpensive heterogeneous silica sulphuric acid (SSA) catalystviaultrasound-assisted (US) synthesis under solvent-free condition. The influences of various parameters such as temperature, catalyst loading, and reaction time on the reaction performance were analysed using a multivariate statistical modelling response surface methodology (RSM). A high yield ofDAPG(95%) was achieved at 60 °C after 15-20 min reaction with the presence of 10% (w/w)SSAas the catalyst. Column chromatography-free and a Gram scale-up reaction also exhibited the practical applicability of this newly developed protocol. TheSSAcatalyst was recovered and recycled up to 10 consecutive runs with no appreciable loss of activity. A plausible mechanism for the Friedel-Crafts acylation of phloroglucinol is proposed. Moreover, an environmental assessment has been carried out over this present method and compared with several established literature using the EATOS software and the Andraos algorithm to assess the consumption of the substrates, solvents, catalysts, and the production of coupled products or by-products. In addition, their energy consumptions were also determined. The data collected showed that the present method is the most promising one, characterised by the highest environmental impact profile against all the other reported methods. The physicochemical properties of the synthesisedDAPGwere assessed and exhibited reasonable oral bioavailability drug property as determined by Lipinski's rules.
- Firdaus, Maulidan,Kusumaningsih, Triana,Prasetyo, Wahyu Eko
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p. 31824 - 31837
(2020/09/17)
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- Expedient Synthesis of Lupulones and Their Derivatization to 2,8-7H-Dihydrochromen-7-ones
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A convenient and improved method for the synthesis of beta acids or lupulones, which are known to possess e. g. anti-cancer, anti-inflammatory, anti-oxidative and antimicrobial activity, has been developed successfully. Further derivatization of these complex structures to the corresponding dihydrochromen-7-ones, including the natural product machuone, was realized to simplify their analysis and to confirm their molecular structure. In addition to practical and safe laboratory procedures, the advantages associated with this new approach involve the use of water as a solvent and the direct crystallization of lupunones from acetonitrile, rendering our strategy more efficient and benign as compared to available methods.
- Blondeel, Eline,D'hooghe, Matthias,Decuyper, Lena,Depetter, Yves,Kaur, Gurkirat,Van Hecke, Kristof,Versyck, Charlotte
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p. 442 - 444
(2020/10/02)
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- Structural optimization and antibacterial evaluation of rhodomyrtosone B analogues against MRSA strains
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Methicillin-resistant Staphylococcus aureus (MRSA) infections are well-known as a significant global health challenge. In this study, twenty-two congeners of the natural antibiotic rhodomyrtosone B (RDSB) were synthesized with the aim of specifically enhancing the structural diversity through modifying the pendant acyl moiety. The structure-activity relationship study against various MRSA strains revealed that a suitable hydrophobic acyl tail in the phloroglucinol scaffold is a prerequisite for antibacterial activity. Notably, RDSB analogue 11k was identified as a promising lead compound with significant in vitro and in vivo antibacterial activities against a panel of hospital mortality-relevant MRSA strains. Moreover, compound 11k possessed other potent advantages, including breadth of the antibacterial spectrum, rapidity of bactericidal action, and excellent membrane selectivity. The mode of action study of compound 11k at the biophysical and morphology levels disclosed that 11k exerted its MRSA bactericidal action by membrane superpolarization resulting in cell lysis and membrane disruption. Collectively, the presented results indicate that the novel modified RDSB analogue 11k warrants further exploration as a promising candidate for the treatment of MRSA infections.
- Zhao, Liyun,Liu, Hongxin,Huo, Luqiong,Wang, Miaomiao,Yang, Bao,Zhang, Weimin,Xu, Zhifang,Tan, Haibo,Qiu, Sheng-Xiang
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supporting information
p. 1698 - 1707
(2018/10/26)
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- Structure-activity relationships and optimization of acyclic acylphloroglucinol analogues as novel antimicrobial agents
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Methicillin-resistant Staphylococcus aureus (MRSA) poses a serious threat to global public health, because it exhibits resistance to existing antibiotics and therefore high rates of morbidity and mortality. In this study, twenty-one natural product-based acylphloroglucinol congeners were synthesized, which possessed different side chains. Antibacterial screening against MRSA strains revealed that acyl moiety tailoring is a prerequisite for the antibacterial activity. Moreover, the lipophilicity, rather than the magnitude of the hydrophobic acyl tail dominates variability in activity potency. Compound 11j was identified as a promising lead for the generation of new anti-MRSA drug development. It was discovered by optimization of the side chain length in light of the potency, the breadth of the antibacterial spectrum, the rate of bactericidal action, as well as the membrane selectivity. Compound 11j exerted profound in?vitro antibacterial activity against the MRSA strain (JCSC 2172), and its MIC was 3-4 orders of magnitude lower than that of vancomycin. A preliminary mode of action study of compound 11j at the biophysical and morphology levels disclosed that the mechanism underlying its anti-MRSA activity included membrane depolarization and, to a lesser extent, membrane disruption and cell lysis.
- Tan, Haibo,Liu, Hongxin,Zhao, Liyun,Yuan, Yao,Li, Bailin,Jiang, Yueming,Gong, Liang,Qiu, Shengxiang
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supporting information
p. 492 - 499
(2016/10/04)
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- Methods of synthesizing alpha acids and substantially enantiomerically pure compositions thereof
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Methods of synthesizing a cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one (“KDT500”) derivative are provided. Such methods may be used to synthesize any desired KDT derivative. In one embodiment, the KDT500 derivative is KDT501.
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Page/Page column 14; Sheet 1
(2016/06/06)
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- METHODS OF SYNTHESIZING ALPHA ACIDS AND SUBSTANTIALLY ENANTIOMERICALLY PURE COMPOSITIONS THEREOF
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Methods of synthesizing a cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one (“KDT500”) derivative are provided. Such methods may be used to synthesize any desired KDT derivative. In one embodiment, the KDT500 derivative is KDT501.
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Paragraph 0012; 0068; 0069
(2015/07/22)
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- Synthesis and P-glycoprotein induction activity of colupulone analogs
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Brain amyloid-beta (Aβ) plaques are one of the primary hallmarks associated with Alzheimer's disease (AD) pathology. Efflux pump proteins located at the blood-brain barrier (BBB) have been reported to play an important role in the clearance of brain Aβ, among which the P-glycoprotein (P-gp) efflux transporter pump has been shown to play a crucial role. Thus, P-gp has been considered as a potential therapeutic target for treatment of AD. Colupulone, a prenylated phloroglucinol isolated from Humulus lupulus, is known to activate pregnane-X-receptor (PXR), which is a nuclear receptor controlling P-gp expression. In the present work, we aimed to synthesize and identify analogs of colupulone that are potent P-gp inducer(s) with an ability to enhance Aβ transport across the BBB. A series of colupulone analogs were synthesized by modifications at both prenyl as well as acyl domains. All compounds were screened for P-gp induction activity using a rhodamine 123 based efflux assay in the P-gp overexpressing human adenocarcinoma LS-180 cells, wherein all compounds showed significant P-gp induction activity at 5 μM. In the western blot studies in LS-180 cells, compounds 3k and 5f were able to induce P-gp as well as LRP1 at 1 μM. The effect of compounds on the Aβ uptake and transport was then evaluated. Among all tested compounds, diprenylated acyl phloroglucinol 5f displayed a significant increase (29%) in Aβ transport across bEnd3 cells grown on inserts as a BBB model. The results presented here suggest the potential of this scaffold to enhance clearance of brain Aβ across the BBB and thus its promise for development as a potential anti-Alzheimer agent.
- Bharate, Jaideep B.,Batarseh, Yazan S.,Wani, Abubakar,Sharma, Sadhana,Vishwakarma, Ram A.,Kaddoumi, Amal,Kumar, Ajay,Bharate, Sandip B.
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p. 5488 - 5496
(2015/05/20)
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- Synthesis and biological evaluation of novel myrtucommulones and structural analogues that target mPGES-1 and 5-lipoxygenase
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The natural acylphloroglucinol myrtucommulone A (1) inhibits microsomal prostaglandin E2 synthase (mPGES)-1 and 5-lipoxygenase (5-LO), and induces apoptosis of cancer cells. Starting from 1 as lead, 28 analogues were synthesized following a straightforward modular strategy with high yielding convergent steps. Major structural variations concerned (I) replacement of the syncarpic acid moieties by dimedone or indandione, (II) cyclization of the syncarpic acid with the acylphloroglucinol core, and (III) substitution of the methine bridges and the acyl residue with isopropyl, isobutyl, n-pentyl or phenyl groups, each. The potency for mPGES-1 inhibition was improved by 12.5-fold for 43 (2-(1-(3-hexanoyl-2,4,6-trihydroxy-5-(1-(3-hydroxy-1-oxo-1H-inden-2-yl)-2-methylpropyl)phenyl)-2-methylpropyl)-3-hydroxy-1H-inden-1-one) with IC50 Combining double low line 0.08 μM, and 5-LO inhibition was improved 33-fold by 47 (2-((3-hexanoyl-2,4,6-trihydroxy-5-((3-hydroxy-1-oxo-1H-inden-2-yl) (phenyl)methyl)phenyl) (phenyl)methyl)-3-hydroxy-1H-inden-1-one) with IC50 Combining double low line 0.46 μM. SAR studies revealed divergent structural determinants for induction of cell death and mPGES-1/5-LO inhibition, revealing 43 and 47 as non-cytotoxic mPGES-1 and 5-LO inhibitors that warrant further preclinical assessment as anti-inflammatory drugs.
- Wiechmann, Katja,Müller, Hans,Huch, Volker,Hartmann, David,Werz, Oliver,Jauch, Johann
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p. 133 - 149
(2015/07/07)
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- Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation
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Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).
- Grenning, Alexander J.,Boyce, Jonathan H.,Porco, John A.
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supporting information
p. 11799 - 11804
(2014/10/16)
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- Synthesis of the acylphloroglucinols rhodomyrtone and rhodomyrtosone B
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In a sequential three-component coupling syncarpic acid, 3-methylbutanal and an acylated phloroglucinol were combined to the hydroxy ketone 3. Acid catalysis converted 3 directly to the natural product rhodomyrtosone B (2). The other isomer, the antibiotic rhodomyrtone (1) was obtained from 3 in a sequence of acid-catalyzed cyclization, retro Friedel-Crafts reaction, and reacylation. In preliminary assays both compounds showed potent antibiotic activity.
- Morkunas, Marius,Dube, Linda,G?tz, Friedrich,Maier, Martin E.
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supporting information
p. 8559 - 8563
(2013/09/12)
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- One pot synthesis and anticancer activity of dimeric phloroglucinols
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A series of dimeric phloroglucinol compounds were synthesized in a single step using commercially available phloroglucinol and methanesulfonic acid. Based on the reported anticancer activity of plant derived dimeric phloroglucinols, these synthesized comp
- Chauthe, Siddheshwar K.,Bharate, Sandip B.,Periyasamy, Giridharan,Khanna, Amit,Bhutani, Kamlesh K.,Mishra, Prabhu D.,Singh, Inder P.
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scheme or table
p. 2251 - 2256
(2012/05/04)
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- The synthesis and anticancer effects of a range of natural and unnatural hop β-acids on breast cancer cells
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The β-acids derived from hops (Humulus lupulus L.) are polyphenols classified as lupulones. As part of our on-going interest in the pharmacognosy of these natural products we were keen to investigate the anticancer activity of lupulone 1 as well as individual lupulone congeners. To achieve this we undertook the synthesis of natural as well as unnatural lupulone derivatives and evaluated them for their anticancer activity against the breast cancer cell lines MCF-7 and MDA-MB-231. The results of our investigations revealed that all of the novel unnatural lupulone derivatives that were synthesised were found to be more toxic to MDA-MB-231 cell lines at 72 h than the parent lupulone 1 itself (except for the α-substituent R1 was CH3). Further investigations confirmed that the novel lupulone derivatives were very efficient at killing cancer cells by apoptosis but appear to do so in a time-dependant process. This outcome may be of great significance as MDA-MB-231 cell lines are characterised by an aggressive phenotype with a propensity to invade other tissue, to form metastases as well as an ability to become insensitive to chemotherapeutic agents.
- Tyrrell, Elizabeth,Archer, Roland,Tucknott, Matt,Colston, Kay,Pirianov, Grisha,Ramanthan, Dharahana,Dhillon, Rajdeep,Sinclair, Alex,Skinner
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scheme or table
p. 144 - 149
(2012/04/23)
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- Biomimetic synthesis and anti-HIV activity of dimeric phloroglucinols
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Plants are an important source of a variety of bioactive compounds with different modes of action. Anti-HIV agents from plant sources can be useful in developing novel therapies for inhibiting HIV infection. Based on the reported anti-HIV activity of plant derived phloroglucinols, several new dimeric phloroglucinols were synthesized in the present study by varying substitution on aromatic ring and at methylene bridge. Some of the synthesized compounds have shown good HIV inhibitory activity in a human CD4+ T cell line (CEM-GFP) infected with HIV-1 NL4.3 virus isolate. Structure-activity studies indicate that phenyl, 4-benzyloxy-1-phenyl and cyclohexyl substitution at methylene bridge gave compounds with better anti-HIV activity. Compounds 22 and 24 showed highest anti-HIV activity with an IC50 of 0.28 μM and 2.71 μM, respectively, former was more active than the positive standard AZT in cell based assay.
- Chauthe, Siddheshwar K.,Bharate, Sandip B.,Sabde, Sudeep,Mitra, Debashis,Bhutani, Kamlesh K.,Singh, Inder P.
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body text
p. 2029 - 2036
(2010/06/12)
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- Discovery of diacylphloroglucinols as a new class of GPR40 (FFAR1) agonists
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In this letter, we report discovery of diacylphloroglucinol compounds as a new class of GPR40 (FFAR1) agonists. Several diacylphloroglucinols with varying length of acyl functionality and substitution on aromatic hydroxyls were synthesized and evaluated for GPR40 agonism using functional calcium-flux assay. Out of 17 compounds evaluated, 14, 17, 19 and 25 exhibited good GPR40 agonistic activity with EC50 values ranging from 0.07 to 8 μM (pEC50 7.12-5.09), respectively, with maximal agonistic response of 84-102%.
- Bharate, Sandip B.,Rodge, Atish,Joshi, Rajendra K.,Kaur, Jaspreet,Srinivasan, Shaila,Senthil Kumar,Kulkarni-Almeida, Asha,Balachandran, Sarala,Balakrishnan, Arun,Vishwakarma, Ram A.
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experimental part
p. 6357 - 6361
(2009/10/01)
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- Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues
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In the present communication, naturally occurring phloroglucinol- monoterpene adducts, euglobals G1-G4 (3b/a and 4a/b) and 16 new analogues (13a/b-18a/b and 19-22) were synthesized by biomimetic approach. These synthetic compounds differ from natural euglobals in the nature of monoterpene and acyl functionality. All of these compounds were evaluated for their antibacterial, antifungal, antileishmanial and antimalarial activities. Analogue 17b possessed good antibacterial activity against methicillin-resistant Staphylococcus aureus, while analogues 19-22 possessed potent antifungal activity against Candida glabrata with IC50s ranging from 1.5 to 2.5 μg/mL. Euglobals along with all synthesized analogues exhibited antileishmanial activity. Amongst these, euglobal G2 (3a), G3 (4a) and analogues 13a and 14a showed potent antileishmanial activity with IC50s ranging from 2.8 to 3.9 μg/mL. Analogue 16a possessed antimalarial activity against chloroquine sensitive D6 clone of Plasmodium falciparum. None of the compounds showed toxicity against mammalian kidney fibroblasts (vero cells) upto the concentration of 4.76 μg/ml.
- Bharate, Sandip B.,Bhutani, Kamlesh K.,Khan, Shabana I.,Tekwani, Babu L.,Jacob, Melissa R.,Khan, Ikhlas A.,Singh, Inder Pal
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p. 1750 - 1760
(2007/10/03)
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- 6-Acyl-4-aryl/alkyl-5,7-dihydroxycoumarins as anti-inflammatory agents
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A series of coumarin derivatives were synthesized in two steps from phloroglucinol. The anti-inflammatory activities of these derivatives were evaluated by means of inhibiting NO production in LPS-induced RAW 264.7 cells. Derivatives 3, 8, 10, 11, and 13 exhibited low micromolar levels of anti-inflammatory activities, and these derivatives also protected DNA against hydroxyl radical attack. Coumarin derivative 8 was the most potent derivative among those tested herein against NO production in LPS-induced RAW 264.7 cells with an IC50 value of 7.6 μM, and it effectively reduced the hydroxyl radical production by 50% at 100 μM in the electron spin resonance study.
- Lin, Chun-Mao,Huang, Sheng-Tung,Lee, Fu-Wei,Kuo, Hsien-Saw,Lin, Mei-Hsiang
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p. 4402 - 4409
(2007/10/03)
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- A two-step biomimetic synthesis of antimalarial robustadials A and B
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The antimalarial robustadials A and B have been synthesized in two steps starting from commercially available phloroglucinol comprising a key biomimetic three-component reaction that involves in situ generation of an o-quinone methide via Knoevenagel cond
- Bharate, Sandip B.,Singh, Inder Pal
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p. 7021 - 7024
(2007/10/03)
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- An efficient two-step synthesis of jensenone isolated from Eucalyptus jensenii. Synthesis of analogues and evaluation as antioxidants
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A phloroglucinol derivative, jensenone (1) isolated from leaves of Eucalyptus jensenii has been synthesized for the first time through a short and efficient two-step procedure starting from commercially available phloroglucinol. The methodology provides a simplified route to introduce diformyl moiety for synthesis of biologically active formylated phloroglucinol compounds such as antimalarial robustadials, cancer chemopreventive euglobals, and antifouling sideroxylonals. Several analogues of jensenone have also been synthesized and evaluated for antioxidant capacity. CSIRO 2005.
- Bharate, Sandip B.,Chauthe, Siddheshwar K.,Bhutani, Kamlesh K.,Singh, Inder P.
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p. 551 - 555
(2007/10/03)
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- Virucidal activity of a β-triketone-rich essential oil of Leptospermum scoparium (manuka oil) against HSV-1 and HSV-2 in cell culture
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The inhibitory activity of manuka oil against Herpes simplex virus type 1 (HSV-1) and Herpes simplex virus type 2 (HSV-2) was tested in vitro on RC-37 cells (monkey kidney cells) using a plaque reduction assay. In order to determine the mode of antiviral
- Reichling, Juergen,Koch, Christine,Stahl-Biskup, Elisabeth,Sojka, Cornelia,Schnitzler, Paul
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p. 1123 - 1127
(2007/10/03)
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- β-triketones from Myrtaceae: Isoleptospermone from Leptospermum scoparium and papuanone from Corymbia dallachiana
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Naturally occurring β-triketones, isoleptospermone [3, 5-hydroxy-4-(2- methyl-1-oxopentyl)-2,2,6,6-tetramethyl-4-cyclohexene-1,3-dione) from Leptospermum scoparium] and papuanone [6, 5-hydroxy-4-(1-oxohexyl)-2,2,6,6- tetramethyl-4-cyclohexene-1,3-dione fr
- Van Klink, John W.,Brophy, Joseph J.,Perry, Nigel B.,Weavers, Rex T.
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p. 487 - 489
(2007/10/03)
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- Inhibitory effect of acylphloroglucinol derivatives on the replication of vesicular stomatitis virus.
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The antiviral activity of natural phloroglucinols and of synthesized mono- and diacylphloroglucinols, and 2,6-diacyl-4,4-dialkylcyclohexa-1,3,5-triones was investigated. A correlation between the acyl chain length and inhibitory activity against vesicular stomatitis virus (VSV) was observed. Potent antiviral activity was found in di-isovalerylphoroglucinol. 2,6-Diacyl-4,4-dialkylcyclohexa-1,3,5-triones inhibited replication of the virus with low cytotoxicity.
- Chiba,Takakuwa,Tada,Yoshii
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p. 1769 - 1772
(2007/10/02)
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- Analogues of natural phloroglucinols as antagonists against both thromboxane A2 and leukotriene D4
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Antagonists against both thromboxane A2 and leukotriene D4 were prepared from phloroglucinol. These compounds showed almost the same activity as the chinesins which were isolated from Hypericum chinense L. The correlation between the
- Tada,Chiba,Takakuwa,Kojima
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p. 1209 - 1212
(2007/10/02)
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- Synthesis of Mammea Coumarins. Part 1. The Coumarins of the Mammea A, B, and C Series
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The naturally-occuring Mammea coumarins of the 4-phenyl-(mammea A), propyl-(mammea B), and 4-pentyl-(mammea C) series have been prepared by Pechmann condensation of an acylphloroglucinol (3-methylbutyryl-, 2-methylbutyryl-, butyryl-, or 2-methylpropionyl-) with the appropriate β-ketoester to give a mixture of 6- and 8-acyl-5,7-dihydroxycoumarins that could be separated.C-Alkylation with 3-methylbut-2-enyl bromide, or 3,7-dimethylocta-2,6-dienyl chloride, in aqueous potassium hydroxide completed the synthesis of the Mammea coumarins having unmodified prenyl or geranyl substituents; oxidative modification of the prenyl group led to the mammea cyclo E and cyclo F coumarins.Some mammea cyclo D (chromeno) coumarins were synthesized by reaction of acylcoumarins with 1,1-dimethoxy-3-methylbutan-3-ol.
- Crombie, Leslie,Jones, Raymond C. F.,Palmer, Christopher J.
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p. 317 - 332
(2007/10/02)
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- Antifungal Activities of 2,4,6-Trihydroxyacylophenones and Related Compounds
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The antifungal activities of sixty two 2,4,6-trihydroxyacylophenones and related compounds against Trichophyton spp. and other fungi were investigated to study their structure-activity relationship.It was found that the activities of these compounds were closely related to the length of the acyl and alkyl chains attached to the 1,3,5-trihydroxybenzene moiety.Among the compounds tested, 2,4,6-trihydroxy-3-nonylacetophenone (V-7) showed the highest activity against Trichophyton spp., with MICs being 1.57 μg/ml, and was more active than amphotericin B.
- Mizobuchi, Shigeyuki,Sato, Yuko
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p. 719 - 724
(2007/10/02)
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- Structure/Activity relationships of Grandinol: a Germination Inhibitor in Eucalyptus
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Structure/activity relationships of grandinol (1), which shows potent inhibition to cress germination, were examined by an activity comparison of many synthetic analogues.The result clearly indicates that a combination of two carbonyl functionalities on a
- Bolte, Matthew L.,Crow, Wilfrid D.,Takahashi, Nobutaka,Sakurai, Akira,Uji-Ie, Masami,Yoshida, Shigeo
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p. 761 - 768
(2007/10/02)
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