- CHRYSOPHAENTIN ANALOGS AND USE THEREOF
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Provided are 9-dechlorochrysophaentin analog compounds and the synthesis process thereof. The disclosed compound have remarkable antimicrobial activitivies that are comparable to, or even more potent than, the natural product chrysophaentin A. Also provided are method of inhibiting bacterial growth or treating bacterial infection by administering an effective amount of the disclosed compounds.
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Paragraph 00138
(2020/10/21)
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- A synthetic approach to chrysophaentin F
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The chrysophaentins are a newly discovered natural product family displaying promising anti-infective activity. Herein we describe an approach to chrysophaentin F that uses an array of metal catalysed coupling reactions (Cu, Ni, Pd, W, Mo) to form key bonds.
- Vendeville, Jean-Baptiste,Matters, Rebecca F.,Chen, Anqi,Light, Mark E.,Tizzard, Graham J.,Chai, Christina L. L.,Harrowven, David C.
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supporting information
p. 4837 - 4840
(2019/05/02)
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- Antifungal activity of cinnamic acid and benzoic acid esters against Candida albicans strains
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Candida albicans is an important opportunistic fungal pathogen capable of provoking infection in humans. In the present study, we evaluated the antifungal effect of 23 ester derivatives of the cinnamic and benzoic acids against 3 C. albicans strains (ATCC-76645, LM-106 and LM-23), as well as discuss their Structure–Activity Relationship (SAR). The antifungal assay results revealed that the screened compounds exhibited different levels of activity depending on structural variation. Among the ester analogues, methyl caffeate (5) and methyl 2-nitrocinnamate (10) were the analogues that presented the best antifungal effect against all C. albicans strains, presenting the same MIC values (MIC?=?128?μg/mL), followed by methyl biphenyl-2-carboxylate (21) (MIC?=?128, 128 and 256?μg/mL for C. albicans LM-106, LM-23, and ATCC-76645, respectively). Our results suggest that certain molecular characteristics are important for the antifungal action.
- Lima, Tamires C.,Ferreira, Alana R.,Silva, Daniele F.,Lima, Edeltrudes O.,de Sousa, Dami?o P.
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p. 572 - 575
(2017/09/30)
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- Partially bio-based poly(amide imide)s by polycondensation of aromatic diacylhydrazides based on lignin-derived phenolic acids and aromatic dianhydrides: Synthesis, characterization, and computational studies
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Two new bio-based diacylhydrazide monomers, namely, 4,4′-(propane-1,3-diylbis(oxy))bis(3-methoxybenzohydrazide) and 4,4′-(propane-1,3-diylbis(oxy))bis(3,5-dimethoxybenzohydrazide) were synthesized starting from lignin-derived phenolic acids, namely, vanillic acid and syringic acid. A series of poly(amide imide)s was synthesized by polycondensation of these diacylhydrazide monomers with commercially available aromatic dianhydrides. Poly(amide imide)s showed inherent viscosity in the range 0.44–0.56 dL?g?1 and exhibited good solubility in organic solvents. Poly(amide imide)s could be cast into transparent, flexible, and tough films from their N,N-dimethylacetamide solutions. Poly(amide imide)s showed 10% weight loss in the temperature range 340–364?°C indicating their good thermal stability. Glass transition temperature (Tg) of poly(amide imides)s were measured by DSC and DMA which were in the range 201–223?°C and 214–248?°C, respectively. The Tg values of poly(amide imide)s were dependent on the number methoxy substituents on aromatic rings of diacylhydrazide monomers. Molecular dynamics simulation studies revealed that chain rigidity is the dominant factor for observed trends in Tg.
- Kuhire, Sachin S.,Sharma, Pragati,Chakrabarty, Suman,Wadgaonkar, Prakash P.
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p. 3636 - 3645
(2017/10/31)
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- Composition FOR PREVENTING ALOPECIA AND ACTIVATING HAIR GROWTH
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The present invention provides a hair growth promoter comprising as an active ingredient, a compound having a chemical structure of general formula (1) or a pharmacologically acceptable salt thereof. In the general formula (1): R_1 is a saturated or unsaturated straight chain or branched C1-C10 alkyl group or hydroxy alkyl group; R_2 is hydrogen or a saturated or unsaturated straight chain or branched C1-C10 alkoxy or hydroxy alkoxy; X is hydrogen, hydroxy, or a saturated or unsaturated straight chain or branched C1-C10 alkyl group, alkoxy or hydroxyl alkoxy; R_3 and R_4 are each independently selected from R_5, hydrogen, aldehyde, and a saturated or unsaturated straight chain or branched alkyl, alkoxy, or hydroxy alkoxy; R_5 has a structure of # AAA #; R_6 is selected from hydrogen, and a saturated or unsaturated straight chain or branched C1-C10 alkyl, alkoxy, or hydroxy alkoxy; and one of R_3 and R_4 is hydrogen.COPYRIGHT KIPO 2017
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Paragraph 0203; 0204
(2018/02/16)
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- Method for selective demethylation of ortho-trimethoxybenzene compounds
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The invention relates to a method for selective demethylation of ortho-trimethoxybenzene compounds and provides a method for preparation of 2,6-dimethoxyphenol derivatives by selective demethylation of ortho-trimethoxybenzene in different substitution types. By taking substitutional or non-substitutional ortho-trimethoxybenzene as a raw material, taking ZrCl4 as a catalyst and taking anisole as an additive, a ratio of the raw material to the catalyst to the additive is optimized in a reaction process to realize selective demethylation at a low reaction temperature ranging from the room temperature to 60 DEG C. The method has the advantages of mild reaction conditions, safety, reliability, low cost and easiness in operation and acquisition of the additive and the catalyst for reaction, simplicity and easiness in separation of reaction products, wide substrate application range and the like. The method effectively improves reaction safety and controllability and has an extensive application prospect in preparation of medicines, material intermediates and fine chemicals.
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- Synthesis and Antileukemic Activities of Piperlongumine and HDAC Inhibitor Hybrids against Acute Myeloid Leukemia Cells
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Synergistic-to-additive antileukemic interactions of piperlongumine (PL) and HDAC inhibitor (HDACi) SAHA (Vorinostat) provide a compelling rationale to construct PL-HDACi hybrids, such as 1-58, which recapitulated the synergism between the parental compounds in high-risk and chemoresistant AML cells. Both PL and HDACi components, either in combination or in hybrid molecules, are essential for inducing significant DNA damage and apoptosis. Introducing C2-chloro substituent to 1-58 yielded 3-35 with increased cytotoxicity but decreased selectivity in noncancerous MCF-10A cells; eliminating C7-C8 olefin of PL obtained 3-31/3-98 scaffolds which were still more active than PL or SAHA in AML and were well-tolerated by MCF-10A cells. The HDACi function was crucial for modulating expression of DNA repair and apoptosis-related proteins. Collectively, PL and SAHA hybrids are potent, multifunctional anti-AML agents, acting in part, by interfering cellular GSH defense, suppressing expression of DNA repair and pro-survival proteins, and inducing expression of pro-apoptotic proteins.
- Liao, Yi,Niu, Xiaojia,Chen, Bailing,Edwards, Holly,Xu, Liping,Xie, Chengzhi,Lin, Hai,Polin, Lisa,Taub, Jeffrey W.,Ge, Yubin,Qin, Zhihui
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p. 7974 - 7990
(2016/09/23)
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- NOVEL BENZAMIDE DERIVATIVE AND USE THEREOF
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Disclosed are a novel benzamide derivative and pharmaceutical use thereof, and more particularly, a novel benzamide derivative having a structure of Formula 1 or pharmaceutically acceptable salts thereof, and a composition for prevention or treatment of pain or itching including the above material. The novel benzamide derivative and pharmaceutically acceptable salt thereof according to the present invention exhibit excellent pain-suppressive effect and, in particular, pain-suppressive effect in not only a neuropathic animal model but also other models such as a formalin model, and therefore, may be used in suppression of different pains such as nociceptive pain, chronic pain, etc. Further, since it was demonstrated that the present invention displays anti-pruritic efficacy even in an itching model, to which a mechanism and treatment concept established with respect to pain is applied, the present invention may also be effectively used in radical treatment of atopic dermatitis by applying the inventive product to an anti-pruritic composition in order to suppress an initial itching stage and treat symptoms thereof, thus preventing skin damage or inflammation after the scratching stage.
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Paragraph 0063-0064
(2014/10/16)
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- NOVEL BENZAMIDE DERIVATIVE AND USE THEREOF
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Disclosed are a novel benzamide derivative and pharmaceutical use thereof, and more particularly, a novel benzamide derivative having a structure of Formula 1 or pharmaceutically acceptable salts thereof, and a composition for prevention or treatment of pain or itching including the above material. The novel benzamide derivative and pharmaceutically acceptable salt thereof according to the present invention exhibit excellent pain-suppressive effect and, in particular, pain-suppressive effect in not only a neuropathic animal model but also other models such as a formalin model, and therefore, may be used in suppression of different pains such as nociceptive pain, chronic pain, etc. Further, since it was demonstrated that the present invention displays anti-pruritic efficacy even in an itching model, to which a mechanism and treatment concept established with respect to pain is applied, the present invention may also be effectively used in radical treatment of atopic dermatitis by applying the inventive product to an anti-pruritic composition in order to suppress an initial itching stage and treat symptoms thereof, thus preventing skin damage or inflammation after the scratching stage.
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Paragraph 0095 - 0098; 0116 - 0119
(2014/11/27)
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- NiCl2·6H2O/NaBH4 in methanol: A mild and efficient strategy for chemoselective deallylation/debenzylation of aryl ethers
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Deprotection of allyl/benzyl aryl ethers was achieved chemoselectively. The mild and inexpensive reagent combination of NiCl2·6H 2O/NaBH4 in methanol afforded the products in high yields, within a reaction time of 5-10 min.
- Chouhan, Mangilal,Kumar, Kapil,Sharma, Ratnesh,Grover, Vikas,Nair, Vipin A.
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supporting information
p. 4540 - 4543
(2013/08/23)
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- Synthesis of leptosin, a glycoside isolated from mānuka honey
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The first synthesis of leptosin, a novel glycoside isolated from mānuka honey is described. Utilising an acetyl protecting group strategy the glycoside was obtained with excellent anomeric selectivity by deploying a Schmidt glycosylation as a key step.
- Aitken, Harry R.M.,Johannes, Manuel,Loomes, Kerry M.,Brimble, Margaret A.
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supporting information
p. 6916 - 6919
(2019/04/10)
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- Chemical interaction between polyphenols and a cysteinyl thiol under radical oxidation conditions
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Chemical interaction between polyphenols and thiols was investigated under radical oxidation conditions using a model cysteinyl thiol derivative, N-benzoylcysteine methyl ester. The radical oxidation was carried out with a stoichiometric amount of 2,2-diphenyl-1-picrylhydrazyl (DPPH), and the decreases in the amounts of polyphenols and the thiol were measured by HPLC analysis. Cross-coupling products between various polyphenols and the thiol were examined by LC-MS in reactions that showed decreases in both the polyphenols and the thiol. The LC-MS results indicated that three phenolic acid esters (methyl caffeate, methyl dihydrocaffeate, and methyl protocatechuate) and six flavonoids (kaempferol, myricetin, luteolin, morin, taxifolin, and catechin) gave corresponding thiol adducts, whereas three polyphenols (methyl ferulate, methyl sinapate, and quercetin) gave only dimers or simple oxidation products without thiol substituents. Thiol adducts of the structurally related compounds methyl caffeate and methyl dihydrocaffeate were isolated, and their chemical structures were determined by NMR analysis. The mechanism for the thiol addition was discussed on the basis of the structures of the products.
- Fujimoto, Aya,Masuda, Toshiya
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experimental part
p. 5142 - 5151
(2012/10/07)
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- Stereoregulations of pyrimidinone based chiral auxiliary in aldol and alkylation reactions: A convenient route to oxyneolignans
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(S)-4-Isopropyl-1-phenyltetrahydropyrimidin-2(1H)-one was synthesized and evaluated as a chiral auxiliary for asymmetric acetate and propionate aldol reactions, by generation of titanium and lithium enolates, affording excellent yields and stereoselectivities for syn and anti aldol diastereomers, respectively. High stereoselectivities were also obtained in lithium mediated alkylation reactions. The application of the auxiliary was exemplified in the asymmetric synthesis of a natural oxyneolignan, (+)-(7S,8S)-4-hydroxy-3, 3′,5′-trimethoxy-8′,9′-dinor-8,4′-oxyneoligna-7, 9-diol-7′-oic acid.
- Chouhan, Mangilal,Sharma, Ratnesh,Nair, Vipin A.
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supporting information
p. 5672 - 5675
(2013/01/15)
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- METHOD FOR THE BREAKDOWN OF LIGNIN
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The invention describes a method for the direct production of molecules with a minimum molecular weight of 78 g/mol by the breakdown of lignin, lignin derivatives, lignin fragments, and/or lignin-containing substances or mixtures in the presence of at least one polyoxometallate and preferably in the presence of a radical scavenger in a liquid medium.
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Page/Page column 5-8
(2010/06/11)
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- Reactions of 2,2-diphenyl-1-picrylhydrazyl (DPPH) with two syringylic phenols or one aroxide derivative
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The reactions between excess 2,2-diphenyl-1-picrylhydrazyl (DPPH) and either 4-hydroxy-3,5-dimethoxybenzaldehyde (syringaldehyde, 1) or methyl 4-hydroxy-3,5-dimethoxyben-zoate (methyl syringate, 2) afford different products from those obtained with the corresponding aroxide (3)of l.In the former case (with the free phenols) the aryloxy (syringyl) group substitutes the 4-nitro group of DPPH, yielding dinitro products 7 and 8 (new stable free radicals) and 9 and 10 (corresponding hydrazines), whereas in the latter case (with the sodium aroxide 3) the aryloxy (syringyl) group substitutes one of the phenyl groups of DPPH in the para position, forming trinitro products 14 (new stable free radical) and 15 (corresponding hydrazine). Accompanying products were isolated by TLC and identified by their 1H NMR, 13C NMR, UV/Vis, and EPR spectra. The reaction mechanisms involving hy-drazyl and aroxyl free radicals are discussed.
- Hristea, Elena N.,Covaci-C?mpeanu, Irina C.,Ioni?ǎ, Gabriela,Ioni?ǎ, Petre,Draghici, Constantin,Cǎproiu, Miron T.,Hillebrand, Mihaela,Constantinescu, Titus,Balaban, Alexandru T.
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experimental part
p. 626 - 634
(2009/07/17)
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- Synthesis and antioxidant activities of 3,5-dialkoxy-4-hydroxycinnamamides
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A series of 3,5-dialkoxy-4-hydroxycinnamamides 6 and 7 was synthesized, and their antioxidant activity was assessed using the thiobarbituric acid reactive substance (TBARS) assay. Interestingly, cinnamamides with longer alkoxy groups on the C-3 and C-5 positions display enhanced inhibition, and most of the compounds in the series tested exhibit excellent lipid peroxidation inhibitory activities. Some cinamamides bearing hexyloxy or 2,6-di-tert-butyl-4-methyl phenol groups have submicromolar inhibitory activities.
- Kang, Tae-Souk,Jo, Hyang-Ok,Park, Woo-Kyu,Kim, Jong-Pyung,Konishi, Yasuo,Kong, Jae-Yang,Park, No-Sang,Jung, Young-Sik
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p. 1663 - 1667
(2008/12/21)
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- Synthesis of diverse analogues of Oenostacin and their antibacterial activities
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Several diverse analogues of Oenostacin, a naturally occurring potent antibacterial phenolic acid derivative, have been synthesized. A small library with more than forty analogues having different aromatic rings and varied side chains has been achieved through solution phase synthesis. Some of these analogues, that is, 22, 23 and 42, possessed potent antibacterial activities against Staphylococcus epidermidis and Staphylococcus aureus having EC50 ranging from 0.49 to 0.67 μM as compared to Oenostacin (EC50 = 0.12 μM).
- Srivastava, Vandana,Darokar, Mahendra P.,Fatima, Atiya,Kumar,Chowdhury, Chinmay,Saxena, Hari Om,Dwivedi, Gaurav R.,Shrivastava, Kunal,Gupta, Vivek,Chattopadhyay,Luqman, Suaib,Gupta,Negi, Arvind S.,Khanuja, Suman P.S.
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p. 518 - 525
(2008/03/12)
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- Simple deprotection of acetal type protecting groups under neutral conditions
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Heating acetals with ethylene glycol causes the deprotection of acetal type protecting groups. When acetals such as MOM ethers, MEM ethers, and THP ethers were heated in ethylene glycol or propylene glycol, solvolysis proceeded smoothly to produce alcohols in excellent yield. This reaction is a very promising method for chemoselective deprotection of acetal type protecting groups.
- Miyake, Hideyoshi,Tsumura, Takatsugu,Sasaki, Mitsuru
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p. 7213 - 7215
(2007/10/03)
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- Depigmenting activity and low cytotoxicity of alkoxy benzoates or alkoxy cinnamte in cultured melanocytes
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To obtain effective and safe topical depigmenting agents, we synthesized hydroxybenzoates, alkoxybenzoates, and 3,4,5-trimethoxycinnamate containing a thymol moiety and screened then for high-level inhibitory activity against melanin synthesis in cultured melanocytes. Eight compounds were tested for their depigmenting effect and cytotoxicity using a murine melanocyte cell line. We found that 3,4,5-trialkoxybenzoates and 3,4,5-trimethoxycinnamate, synthesized by conjugating 3,4,5-trialkoxybenzoic acids and 3,4,5-trimethoxycinnmic acid with thymol, showed a potent depigmenting effect and low cytotoxicity. Compound 4h, 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate, showed the most potent depigmenting effect (IC50=10 μM) with low cytotoxicity (IC50=200 μM).
- Kang, Hak Hee,Rho, Ho Sik,Hwang, Jae Sung,Oh, Seong-Geon
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p. 1085 - 1088
(2007/10/03)
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- Pyrrolobenzodiazepines
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Compounds of the formulae Ia and Ib: wherein: A is CH2, or a single bond; R2 is selected from: R, OH, OR, CO2H, CO2R, COH, COR, SO2R, CN; R6, R7 and R9 are independently selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn; and R8 is selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn, where R is as defined above, or the compound is a dimer with each monomer being the same or different and being of formula Ia or Ib, where the R8 groups of the monomers form together a bridge having the formula —X—R′—X— linking the monomers, where R′ is an alkylene chain containing from 3 to 12 carbon atoms, which chain may be interrupted by one or more hetero-atoms and/or aromatic rings and may contain one or more carbon-carbon double or triple bonds, and each X is independently selected from O, S, or N; except that in a compound of formula Ia when A is a single bond, then R2 is not CH═CH(CONH2) or CH═CH(CONMe2). Other related compounds are also disclosed.
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- Pyrrolobenzodiazepines
-
Compounds of the formulae Ia and Ib: wherein:A is CH2, or a single bond;R2 is selected from: R, OH, OR, CO2H, CO2R, COH, COR, SO2R, CN;R6, R7 and R9 are independently selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn;and R8 is selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn, where R is as defined above, or the compound is a dimer with each monomer being the same or different and being of formula Ia or Ib, where the R8 groups of the monomers form together a bridge having the formula -X-R'-X- linking the monomers, where R' is an alkylene chain containing from 3 to 12 carbon atoms, which chain may be interrupted by one or more hetero-atoms and/or aromatic rings and may contain one or more carbon-carbon double or triple bonds, and each X is independently selected from O, S, or N; except that in a compound of formula Ia when A is a single bond, then R2 is not CH=CH(CONH2) or CH=CH(CONMe2). Other related compounds are also disclosed.
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- Selective hydroxy group protection of gallic acid
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An efficient procedure allowing selective differentiation of the 4-hydroxy group of methyl gallate was reported.
- Zhu, Jieping,Chastanet, Jacqueline,Beugelmans, Rene
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p. 2479 - 2486
(2007/10/03)
-
- Studies on the constituents of the bark of Kalopanax pictus Nakai
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Five new compounds, kalopanaxsaponin G (2) and kalopanaxins A (6), B (8), C (11) and D (13), were isolated from the bark of Kalopanax pictus together with nine known compounds, kalopanaxsaponins A (1) and B (5), pericarpsaponin P(J3) (3), hederasaponin B (4), syringin (7), protocatechuic acid (9), coniferin (10), liriodendrin (=dl-syringaresinol di-O-glucopyranoside) (12), glucosyringic acid (14) and chlorogenic acid (15). The structures of the new compounds were characterized as hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D- glucopyranoside (2), ferulylaldehyde (=coniferylaldehyde) 4-O-β-D-glucopyranoside (6), coniferin 6'-O-(4-O-α-L-rhamnopyranosyl)-syringate (8), 2-methoxyhydroquinone 4-O-[6-O[(4-O-α-L-rhamnopyranosyl)-syringyl]-β-D-glucopyranoside (11) and coniferyl alcohol 4-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside (=coniferin 2'-O-β-D-apiofuranoside) (13).
- Sano,Sanada,Ida,Shoji
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p. 865 - 870
(2007/10/02)
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- Boron Trichloride as a Selective Demethylating Agent for Hindered Ethers: a Synthesis of the Phytoalexins α- and β-Pyrufuran, a Synthesis of Tri-O-methylleprolomin and its Demethylation
-
Boron trichloride has been found to be an efficient reagent for the selective cleavage of sterically hindered methoxy groups in methoxyarenes.The scope and utility of this reaction are explored with examples drawn from derivatives of benzene, naphtalene, 9,10-dihydrophenanthrene and dibenzofuran.The method is applied to the synthesis of the phytoalexins α- (56) and β-pyrofuran (58) (1,3,4-trimethoxydibenzofuran-2-ol and 1,2,4-trimethoxydibenzofuran-3-ol).A synthesis of tri-O-methylleprolomin (61), a derivative of the unusual lichen metabolite leprolomin (60), is described and its demethylation with boron trichloride is studied.
- Carvalho, Christopher F.,Russo, Albert V.,Sargent, Melvyn V.
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p. 777 - 792
(2007/10/02)
-
- Boron Trichloride as a Selective Demethylating Agent for Hindered Ethers
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Boron trichloride has been found to be an efficient reagent for the selective cleavage of sterically hindered methoxy groups in methoxyarenes; the scope and utility of this reaction are explored.
- Carvalho, Christopher F.,Sargent, Melvyn V.
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p. 227 - 229
(2007/10/02)
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