- Synthesis and antioxidant activities of berberine 9-: O -benzoic acid derivatives
-
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.
- 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)
-
- COMPOUNDS AND METHODS OF INHIBITING BACTERIAL CHAPERONIN SYSTEMS
-
The present disclosure relates to novel compounds and methods of killing or inhibiting the growth of bacteria. In some embodiments, a method of killing or inhibiting the growth of bacteria is provided. The method comprises administering a compound of formula I or a pharmaceutically acceptable salt thereof to bacteria. In some embodiments, a method of killing or inhibiting the growth of bacteria is provided. The method comprises administering an anthelmintic to bacteria.
- -
-
Paragraph 0210; 0211
(2020/05/28)
-
- A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide
-
A convenient, rapid H2SO4-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H2SO4 using N-chlorosuccinimide and N-iodosuccinimide, respectively.
- Wu, Yong-Qi,Lu, Hai-Jia,Zhao, Wen-Ting,Zhao, Hong-Yi,Lin, Zi-Yun,Zhang, Dong-Feng,Huang, Hai-Hong
-
supporting information
p. 813 - 822
(2020/02/15)
-
- Divergent Synthesis of Natural Benzyl Salicylate and Benzyl Gentisate Glucosides
-
Herein is reported the first total synthesis of benzyl salicylate and benzyl gentisate glucosides present in various plant species, in particular the Salix genus, such as Populus balsamifera and P. trichocarpa. The method permits the synthesis of several natural phenolic acid derivatives and their glucosides starting from salicylic or gentisic acid. The divergent approach afforded access to three different acetylated glucosides from a common synthetic intermediate. The key step in the total synthesis of naturally occurring glycosides - the selective deacetylation of the sugar moiety - was achieved in the presence of a labile benzyl ester group by employing mild deacetylation conditions. The protocol permitted synthesis of trichocarpine (4 steps, 40% overall yield), isotrichocarpine (3 steps, 51% overall yield), trichoside (6 steps, 40% overall yield), and deoxytrichocarpine (3 steps, 42% overall yield) for the first time (>95% purity). Also, the optimized mild deacetylation conditions allowed synthesis of 2-O-acetylated derivatives of all four glycosides (5-17% overall yield, 90-95% purity), which are rare plant metabolites.
- Fedorova, Dariya D.,Nazarova, Dariya S.,Avetyan, David L.,Shatskiy, Andrey,Belyanin, Maxim L.,K?rk?s, Markus D.,Stepanova, Elena V.
-
p. 3173 - 3180
(2020/11/02)
-
- Design, synthesis, and preliminary biological evaluation of 3′,4′,5′-trimethoxy flavonoid salicylate derivatives as potential anti-tumor agents
-
According to the pharmacophore combination principle, a set of new 3′,4′,5′-trimethoxy flavonoid salicylate derivatives were designed, synthesized, and evaluated for biological activity. The cytotoxicity evaluation revealed that compound 10v exhibited higher potency than 5-Fu against HCT-116 cells. Preliminary biological activity studies showed that compound 10v could inhibit the colony formation and migration of HCT-116 cells. Besides, the Hoechst 33258 staining assay and flow cytometry revealed that treatment with compound 10v induced the apoptosis of HCT-116 cells in a concentration-dependent manner, while it had no effect on their cell cycle. The WB analysis suggested that HIF-1α, tubulin, HK-2, and PFK might be the potential pharmacophore targets of compound 10v. Tubulin was a potential drug target for compound 10v, which was explained by analyzing the crystal structure of compound 10v complexed with tubulin. These results indicated that compound 10v might be a promising anti-tumor agent candidate, deserving further optimization and evaluation.
- Deng, Xiangping,Liu, Renbo,Li, Junjian,Li, Zhongli,Liu, Juan,Xiong, Runde,Lei, Xiaoyong,Zheng, Xing,Xie, Zhizhong,Tang, Guotao
-
p. 1874 - 1884
(2019/01/28)
-
- Hydroxybiphenylamide GroEL/ES Inhibitors Are Potent Antibacterials against Planktonic and Biofilm Forms of Staphylococcus aureus
-
We recently reported the identification of a GroEL/ES inhibitor (1, N-(4-(benzo[d]thiazol-2-ylthio)-3-chlorophenyl)-3,5-dibromo-2-hydroxybenzamide) that exhibited in vitro antibacterial effects against Staphylococcus aureus comparable to vancomycin, an antibiotic of last resort. To follow up, we have synthesized 43 compound 1 analogs to determine the most effective functional groups of the scaffold for inhibiting GroEL/ES and killing bacteria. Our results identified that the benzothiazole and hydroxyl groups are important for inhibiting GroEL/ES-mediated folding functions, with the hydroxyl essential for antibacterial effects. Several analogs exhibited >50-fold selectivity indices between antibacterial efficacy and cytotoxicity to human liver and kidney cells in cell culture. We found that MRSA was not able to easily generate acute resistance to lead inhibitors in a gain-of-resistance assay and that lead inhibitors were able to permeate through established S. aureus biofilms and maintain their bactericidal effects.
- Kunkle, Trent,Abdeen, Sanofar,Salim, Nilshad,Ray, Anne-Marie,Stevens, McKayla,Ambrose, Andrew J.,Victorino, José,Park, Yangshin,Hoang, Quyen Q.,Chapman, Eli,Johnson, Steven M.
-
p. 10651 - 10664
(2019/01/04)
-
- Transition-metal-free decarboxylative bromination of aromatic carboxylic acids
-
Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.
- Quibell, Jacob M.,Perry, Gregory J. P.,Cannas, Diego M.,Larrosa, Igor
-
p. 3860 - 3865
(2018/04/26)
-
- Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings
-
Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.
- Perry, Gregory J. P.,Quibell, Jacob M.,Panigrahi, Adyasha,Larrosa, Igor
-
supporting information
p. 11527 - 11536
(2017/08/30)
-
- C- ARYL GLYCOSID DERIVATIVES, PHARMACEUTICAL COMPOSITION, PREPARATION PROCESS AND USES THEREOF
-
This invention relates to a kind of C-aryl glycoside derivatives, its pharmaceutical compositions, preparation methods, and uses thereof. The preparation method comprises: method 1: in a solvent, deprotecting the acetyl protecting groups of compound 1-f in the presence of a base; method 2: 1) compound 2-g reacts with via Mitsunobu reaction; 2) deprotecting the acetyl protecting groups of compound 2-f obtained from step 1; method 3: 1) compound 2-g reacts with via nucleophilic substitution reaction; 2) deprotecting the acetyl protecting groups of compound 3-f obtained from step 1. The pharmaceutical composition comprises a kind of C-aryl glycoside derivatives; it's pharmaceutically acceptable salts and/or prodrugs thereof and excipient thereof. This invention further relates to a kind of C-aryl glycoside derivatives, it's pharmaceutically acceptable salts or pharmaceutical compositions thereof for the use in preparation of a SGLT inhibitor. The C-aryl glycoside derivatives of this invention provides a new direction for the study of SGLT inhibitors.
- -
-
Paragraph 0121; 0122 0123
(2017/04/19)
-
- A cyclotrimethoxone-substituted salicylate compound and anti-tumor effect thereof
-
The invention relates to the technical field of medicines, and designs and synthesizes a novel A cyclotrimethoxy 4'-hydroxyflavone compound and an A cyclotrimethoxone-substituted salicylate compound. The figure 1 is a general formula of the A cyclotrimethoxone-substituted salicylate compound, wherein in the formula, R1, R2 and R3 are equal to OCH3 or R2, R3 and R4 are equal to OCH3; R5- is equal to OCH3, CH3, F, Cl, Br, I or the like. The novel A cyclotrimethoxy 4'-hydroxyflavone compound and the A cyclotrimethoxone-substituted salicylate compound can have an obvious inhibiting effect on MGC-803 (human gastric carcinoma cells), HepG2 (human hepatoma carcinoma cells), MCF-7 (human breast cancer cells) and hopefully become anti-tumor drugs. The invention discloses a preparation method of the novel A cyclotrimethoxy 4'-hydroxyflavone compound and the A cyclotrimethoxone-substituted salicylate compound.
- -
-
Paragraph 0038-0040
(2017/07/19)
-
- Design, synthesis and biological evaluation of flavonoid salicylate derivatives as potential anti-tumor agents
-
A series of flavonoid salicylate derivatives containing trimethoxybenzene and a series of chrysin salicylate derivatives were synthesized for use as anti-tumor agents, and evaluated for antiproliferative activity using three human tumor cells: MCF-7 (breast carcinoma cells), HepG2 (liver carcinoma cells), MGC-803 (gastric carcinoma cells) and the mice tumor cells MFC (forestomach carcinoma cells). A substituent group of a suitable size and the trimethoxybenzene had a certain influence on the bioactivity of the flavonoid salicylate derivatives. Compound 2 and its salicylate derivatives 7a-7g containing the trimethoxybenzene exhibited more antiproliferative activity. Among them, compound 7g displayed the most potent antiproliferative activity against MGC-803 cells and MFC cells with the concentration causing 50% inhibition of cell growth (IC50) values of 11.05 ± 1.58 μM and 13.73 ± 2.04 μM, respectively. The flow cytometry results showed that compound 7g caused the cell cycle to be arrested in the G0/G1 phase and induced apoptosis of MFC cells in a dose-dependent manner. Furthermore, compound 7g showed good anti-tumor activity in vivo. These results suggested that compound 7g could be a new, potent anti-tumor candidate which should be optimized and evaluated further.
- Deng, Xiangping,Wang, Zhe,Liu, Juan,Xiong, Shujuan,Xiong, Runde,Cao, Xuan,Chen, Yanming,Zheng, Xing,Tang, Guotao
-
p. 38171 - 38178
(2017/08/16)
-
- Copper-catalyzed formal c-h carboxylation of aromatic compounds with carbon dioxide through arylaluminum intermediates
-
The C-H bond carboxylation of various aromatic compounds with CO2 was achieved by the deprotonative alumination with a mixed alkyl amido lithium aluminate compound iBu3Al(TMP)Li followed by the NHC-copper-catalyzed carboxylation of the resulting arylaluminum species, which afforded the corresponding carboxylation products in high yield and high selectivity. In addition to benzene derivatives, heteroarenes such as benzofuran, benzothiophene, and indole derivatives are also suitable substrates. Functional groups such as Cl, Br, I, vinyl, amide, and CN could survive the reaction conditions. Some key reaction intermediates such as the copper aryl and isobutyl complexes and their carboxylation products were isolated and structurally characterized by X-ray crystallographic analyses, thus offering important information on the reaction mechanism.
- Ueno, Atsushi,Takimoto, Masanori,Wylie,Nishiura, Masayoshi,Ikariya, Takao,Hou, Zhaomin
-
supporting information
p. 1010 - 1016
(2015/03/31)
-
- Room-temperature ortho-alkoxylation and -halogenation of N-tosylbenzamides by using palladium(II)-catalyzed C-H activation
-
The N-tosylcarboxamide group can direct the room-temperature palladium-catalyzed C-H alkoxylation and halogenation of substituted arenes in a simple and mild procedure. The room-temperature stoichiometric cyclopalladation of N-tosylbenzamide was first studied, and the ability of the palladacycle to react with oxidants to form C-X and C-O bonds under mild conditions was demonstrated. The reaction conditions were then adapted to promote room-temperature ortho-alkoxylations and ortho-halogenations of N-tosylbenzamides using palladium as catalyst. The scope and limitation of both alkoxylations and halogenations was studied and the subsequent functional transformation of the N-tosylcarboxamide group through nucleophilic additions was evaluated. This methodology offers a simple and mild route to diversely functionalized arenes.
- Peron, Florent,Fossey, Christine,Sopkova-Deoliveirasantos, Jana,Cailly, Thomas,Fabis, Frederic
-
p. 7507 - 7513
(2014/06/23)
-
- Exploring the scope of pyridyl- and picolyl-functionalized 1,2,3-triazol-5-ylidenes in bidentate coordination to ruthenium(II) cymene chloride complexes
-
1-(2-Pyridyl)-, 4-(2-pyridyl)-, 1-(2-picolyl)-, and 4-(2-picolyl)- functionalized 1,3,4-trisubstituted 1,2,3-triazolium salts (1A-D, respectively) were investigated as N-heterocyclic carbene (trzNHC) precursors for bidentate coordination to ruthenium(II) through the CNHC and N pyridyl donors. In addition to the pyridyl and picolyl pendant groups, a variety of para-substituted phenyl rings were attached to the 1,2,3-triazolylidene via carbon or nitrogen atoms. The ruthenation was accomplished by metalation with Ag2O to form intermediate silver carbene complexes and subsequent transmetalation with [Ru(η6-p- cymene)Cl2]2. The cationic ruthenium complexes [Ru(η6-p-cymene)(trzNHC)Cl]+ (3A-C) were readily obtained with 1-(2-pyridyl)-, 4-(2-pyridyl)-, and 1-(2-picolyl)-1,2,3-triazolium salts (1A-C) but not with the 4-picolyl analogue (1D). The bidentate coordination of the ligand precursors 1 was followed by multinuclear NMR spectroscopy, revealing significant changes in chemical shifts for triazole C-5, pyridine nitrogen atoms, and the neighboring α-proton (H-6 pyridyl) in 13C, 15N, and 1H NMR spectra. The molecular composition of complexes 3A-C was confirmed by elemental analysis and positive ion electrospray ionization (ESI+) mass spectra, the latter showing ions corresponding to [Ru(η6-p-cymene)(trzNHC)Cl] +. The solid-state structures of the three representative complexes were confirmed by single-crystal X-ray analyses; all complexes displayed a typical piano-stool type configuration. Preliminary catalytic activity screening of 3A-C in the oxidation of selected primary and secondary alcohols with tert-butyl hydroperoxide (TBHP) to give carbonyl compounds is also discussed.
- Bolje, Aljosa,Hohloch, Stephan,Urankar, Damijana,Pevec, Andrej,Gazvoda, Martin,Sarkar, Biprajit,Kosmrlj, Janez
-
p. 2588 - 2598
(2014/06/10)
-
- NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF
-
The present invention relates to compounds of formula (I), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, formula (I). wherein R1, R2, R3, R4, and L1 are defined in the specfication, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions. The present invention also relates to compounds of formula (II), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, formula (II). wherein R1a, R2a, Rx, and n are as defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.
- -
-
Page/Page column 130
(2009/06/27)
-
- Hydroxylated 1,2,4-oxadiazole benzoic acid compounds, composistions thereof and the use for nonsense suppression
-
Novel hydroxylated 1,2,4-oxadiazole benzoic acid compounds, methods of using and pharmaceutical compositions comprising a hydroxylated 1,2,4-oxadiazole benzoic acid derivative are disclosed. The methods include methods of treating or preventing a disease
- -
-
Page/Page column 19
(2008/12/06)
-
- Design, synthesis, and pharmacological evaluation of N-bicyclo-5-chloro-1H-indole-2-carboxamide derivatives as potent glycogen phosphorylase inhibitors
-
As a result of the various N-bicyclo-5-chloro-1H-indole-2-carboxamide derivatives with a hydroxy moiety synthesized in an effort to discover novel glycogen phosphorylase (GP) inhibitors, 5-chloro-N-(5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1H-indole-2
- Onda, Kenichi,Shiraki, Ryota,Ogiyama, Takashi,Yokoyama, Kazuhiro,Momose, Kazuhiro,Katayama, Naoko,Orita, Masaya,Yamaguchi, Tomohiko,Furutani, Masako,Hamada, Noritaka,Takeuchi, Makoto,Okada, Minoru,Ohta, Mitsuaki,Tsukamoto, Shin-ichi
-
experimental part
p. 10001 - 10012
(2009/04/06)
-
- NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF
-
The present invention relates to compounds of formula (I), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, and L1 are defined in the specfication, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions. The present invention also relates to compounds of formula (II), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R1a, R2a and (Rx)n are as defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.
- -
-
Page/Page column 52
(2008/06/13)
-
- Discovery and SAR studies of novel GlyT1 inhibitors
-
Inhibition of the glycine transporter GlyT1 is a potential strategy for the treatment of schizophrenia. A novel series of GlyT1 inhibitors and their structure-activity relationships (SAR) are described. Members of this series are highly potent and selective transport inhibitors which are shown to elevate glycine levels in cerebrospinal fluid.
- Walter, Magnus W.,Hoffman, Beth J.,Gordon, Kimberly,Johnson, Kirk,Love, Patrick,Jones, Matthew,Man, Teresa,Phebus, Lee,Reel, Jon K.,Rudyk, Helene C.,Shannon, Harlan,Svensson, Kjell,Yu, Hong,Valli, Matthew J.,Porter, Warren J.
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p. 5233 - 5238
(2008/03/14)
-
- In vitro affinities of various halogenated benzamide derivatives as potential radioligands for non-invasive quantification of D2-like dopamine receptors
-
Benzamide derivatives as radiotracers have played an important role in diagnosing malfunction in dopaminergic neurotransmission. A variety of halogenated and two unsubstituted benzamide derivatives were synthesised and their in vitro affinities to dopaminergic, serotonergic and adrenergic receptors and their lipophilicities were determined. As references IBZM (3), raclopride (4) and FLB457 (5) were tested as well. The two iodinated compounds NAE (27) and NADE (28) displayed Ki values of 0.68 and 14 nM for the D2 receptor. The well-established radiotracers FP (1) and DMFP (2) showed affinities in the same range as did the brominated compounds NABrE (29) and NABrDE (30). The log D7.4 values of 2.91 for NAE (27) and of 2.81 for NADE (28) are in the range of those found for IBZM (3), FP (1) and DMFP (2). These facts allow to expect good properties for the two iodinated compounds NAE (27) and NADE (28) regarding in vivo imaging with SPECT.
- Stark, Daniela,Piel, Markus,Huebner, Harald,Gmeiner, Peter,Gruender, Gerhard,Roesch, Frank
-
p. 6819 - 6829
(2008/03/27)
-
- Enforcing periodic secondary structures in hybrid peptides: A novel hybrid foldamer containing periodic γ-turn motifs
-
This note describes the design, synthesis, and conformational studies of a novel hybrid foldamer that adopts a definite compact, three-dimensional structure determined by a combined effect of the special conformational properties of the foldamer constituents. The striking feature of this de novo designed foldamer is its ability to display periodic γ-turn conformations stabilized by intramolecular hydrogen bonds. Conformational investigations by single-crystal X-ray studies, solution-state NMR, and ab initio MO theory at the HF/6-31G* level strongly support the prevalence of γ-turn motifs in both the di- and tetrapeptide foldamers, which are presumably stabilized by bifurcated hydrogen bonds in the solid and solution states. The strategy disclosed herein for the construction of hybrid foldamers with periodic γ-turn motifs has the potential to significantly augment the conformational space available for foldamer design with diverse backbone structures and conformations.
- Baruah, Pranjal K.,Sreedevi,Gonnade, Rajesh,Ravindranathan, Sapna,Damodaran, Krishnan,Hofmann, Hans-Joerg,Sanjayan, Gangadhar J.
-
p. 636 - 639
(2007/10/03)
-
- BENZAMIDE DERIVATIVE
-
To provide compounds which have high angiogenesis inhibiting activity, and are useful as agents for effective treatment and prevention of diseases involving pathologic angiogenesis, for example, cancer and cancer metastasis, methods for producing the comp
- -
-
Page/Page column 32
(2010/11/23)
-
- COMPOUNDS FOR THE TREATMENT OF DISEASES ASSOCIATED WITH THE FORMATION OF AMYLOID FIBRILS
-
SUMMARY The present invention provides new amyloidogenesis inhibiting compounds of formula (I): in which R1 is a -NRaRb group, where Ra and Rb, independently, are a hydrogen atom or a C1-C
- -
-
Page/Page column 10-11
(2008/06/13)
-
- 2-ARYLOXYETHYL GLYCINE DERIVATIVES AND THEIR USE AS GLYCINE TRANSPORT INHIBITORS
-
The present invention relates to certain 2-aryloxyethyl glycine derivatives that exhibit activity as inhibitors of the glycine type-1 transporter, to pharmaceutical compositions containing them and to their use in the treatment of neurological and neuropsychiatric disorder.
- -
-
Page/Page column 35-36
(2010/02/14)
-
- Novel polyphenylenes containing phenol-substituted oxadiazole moieties as fluorescent chemosensors for fluoride ion
-
Novel phenyl-based conjugated polymers with different content of 2,5-bis(2-hydroxyphenyl)-1,3,4-oxadiazole (1) or 2-(2-hydroxyphenyl)-5-phenyl-1, 3,4-oxadiazole (2) units in the main chain were synthesized through Suzuki coupling. The measurements of sens
- Zhou, Gang,Cheng, Yanxiang,Wang, Lixiang,Jing, Xiabin,Wang, Fosong
-
p. 2148 - 2153
(2007/10/03)
-
- Acyl derivatives of 2-aminobenzimidazole and their fungicide activity
-
Procedures have been developed for the preparation of methyl 2-benzimidazolylcarbamate, 2-acetylaminobenzimidazole, 2- benzoylaminobenzimidazole, 2-(3,5-dibromo-2-hydroxybenzoylamino)benzimidazole, 1-(3,6-dichloro-2-methoxybenzoyl)-2-aminobenzimidazole, 2-(3,5-dichloro-2- hydroxybenzoylamino)benzimidazole, 2-(3,5-dichloro-2-methoxybenzoylamino) benzimidazole, and 1-(3,5,6-trichloro-2-methoxybenzoyl)-2-aminobenzimidazole. The synthesized compounds have been tested for fungicide activity.
- Pilyugin,Sapozhnikov,Sapozhnikova
-
p. 738 - 743
(2007/10/03)
-
- Proteomimetic compounds and methods
-
The present invention relates to compounds and pharmaceutical compositions which are proteomimetic and to methods for inhibiting the interaction of an alpha-helical protein with another protein or binding site. Methods for treating diseases or conditions which are modulated through interactions between alpha helical proteins and their binding sites are other aspects of the invention.
- -
-
-
- Bromodecarbonylation and bromodecarboxylation of electron-rich benzaldehydes and benzoic acids with oxone and sodium bromide
-
Benzaldehydes and benzoic acids bearing ortho- and paraelectron donating substituents having unshared electron-pair have undergone bromodecarbonylation or bromodecarboxylation on treatment with sodium bromide in the presence of Oxone in aqueous methanol.
- Koo, Bon-Suk,Kim, Eun-Hoo,Lee, Kee-Jung
-
p. 2275 - 2286
(2007/10/03)
-
- An extended β-strand mimic for a larger artificial β-sheet
-
This paper reports the development of β-strand mimic B, which duplicates the hydrogen-bonding functionality of one edge of a tetrapeptide β-strand. When attached to a tripeptide by a suitable linking group, β- strand mimic B forms a hydrogen-bonded antiparallel β-sheet structure, artificial β-sheet 2. β-Strand mimic B is based upon a 5-hydrazino-2- metboxybenzoic acid building block. The first half of the paper describes synthetic, IR and 1H NMR spectroscopic, X-ray crystallographic, and molecular modeling studies of 5-hydrazino-2-methoxybenzoic acid derivatives and related molecules. These studies establish that hydrazide derivatives of 5-hydrazino-2-methoxybenzoic acid adopt a conformation similar to that of a peptide β-strand and are suitable for use as β-strand mimics. The second half of the paper describes synthetic and 1H NMR spectroscopic studies of artificial β-sheet 2 and of controls 20 and 21, which resemble the peptidomimetic and peptide strands of 2. These experiments indicate that 2 adopts a conformation and hydrogen-bonding pattern similar to that of an antiparallel β-sheet and establish that β-strand mimic B can induce β- sheet formation in an attached peptide strand.
- Nowick, James S.,Pairish, Mason,Lee, In Quen,Holmes, Darren L.,Ziller, Joseph W.
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p. 5413 - 5424
(2007/10/03)
-
- Synthesis of a carbon-14 labelled version of benzofuran GR151004B
-
The 5HT1 receptor agonist GR1510048 (2b), labelled with carbon-14 at C-3 of the benzofuran ring, was prepared in 19% overall yield in five steps from 5-bromo-2-methoxybenzoic [14C]acid (3b).
- Wadsworth, Alan H.,Mitchell, Heather A.,Fellows, Lan,Sutherland, Derek R.
-
p. 863 - 871
(2007/10/03)
-
- The Bromination of Phenolic Methyl Ethers with Hydrogen Bromide using Sodium Tungstate and Hydrogen Peroxide as Oxidant
-
Sodium tungstate has been found to be an effective catalyst for the nuclear bromination of some aromatic methyl ethers using hydrogen bromide in glacial acetic acid and hydrogen peroxide as the oxidant.
- Bezodis, Paul,Hanson, James R.,Petit, Philippe
-
p. 334 - 335
(2007/10/03)
-
- N-bromosuccinimide/dibromodimethylhydantoin in aqueous base: A practical method for the bromination of activated benzoic acids
-
A new bromination method employing NBS or dibromodimethylhydantoin in aqueous base is described for the synthesis of 3-bromo-2,6-dimethoxybenzoic acid (1) and other monobrominated alkoxybenzoic acids.
- Auerbach, Joseph,Weissman, Steven A.,Blacklock, Thomas J.,Angeles, Marshall R.,Hoogsteen, Karst
-
p. 931 - 934
(2007/10/02)
-
- Marine Bacteria, I. - Synthesis of Pentabromopseudiline, a Cytotoxic Phenylpyrrole from Alteromonas luteo-violaceus
-
A new synthesis of 2,3,4-tribromo-5-(3,5-dibromo-2-hydroxyphenyl)pyrrole (1a, pentabromopseudiline), an antibiotic, enzymeinhibitory and cytotoxic active constituent of the marine bacterium Alteromonas luteo-violaceus, is described.For investigation of structure-activity relationships further 2-phenylpyrroles are investigated.Key step in their synthesis is the Grignard reaction of 2-(1,3-dioxan-2-yl)ethylmagnesium bromide (9d) with benzoyl chlorides yielding γ-phenyl-γ-ketoaldehydes 24, and the Paal-Knorr cyclisation of the latter. - Key Words: Alteromonas luteo-violaceus / Bromopyrrole / Marine bacteria / Pentabromopseudiline
- Laatsch, Hartmut,Pudleiner, Heinz
-
p. 863 - 882
(2007/10/02)
-
- Metal Alkoxide Modified Organometallic Reagents. Preparation and Stability of Organolithium Reagents in Tetrahydrofuran in the Presence of Magnesium 2-Ethoxyethoxide
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The metalating ability of alkyllithium reagents and their tendency to cleave THF are greatly diminished in the presence of magnesium 2-ethoxyethoxide, 1.Advantage may be taken of this to generate organolithium reagents in THF in the presence of 1 under conditions not normally favorable to their stability.Thus, by reaction with metallic lithium in the presence of 1 in THF, the compounds RX (R = n-Bu, s-Bu, t-Bu, cyclohexyl, menthyl, p-methoxyphenyl, o-(methoxymethyl)phenyl; X = Cl, Br) have been converted to the corresponding organometallic reagents.In the absence of 1 the alkyllithium reagents formed react with the solvent, resulting in reduced yields and often alternative products.In the case of the preparation of the arylmetal reagents the presence of 1 suppresses either subsequent orthometalation (R = p-methoxyphenyl) or Wittig rearrangement (R = o-(methoxymethyl)phenyl) to give a clean replacement of halogen by the metal.The presence of THF is also tolerated in the preparation of these two arylmetal reagents by halogen-metal exchange using n-butyllithium in the presence of 1 whereas if 1 is absent little or none of the desired product is obtained.
- Screttas, Constantinos G.,Steele, Barry R.
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p. 1013 - 1017
(2007/10/02)
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- The Bromination of Salicylate Anions. Evidence for the Participation of the Ortho Carboxylate Group
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Salicylate monoanions show reduced selectivity toward bromine in aqueous solution when compared to similarly substituted phenols.In particular, 5-substituted salicylate ions show ρ+ = -2.69 whereas for para-substituted phenols ρ+ = -5.21.From this and other evidence it is argued that bromine attack on such ions may involve proton transfer from the hydroxyl group to the o-carboxylate to which it is hydrogen bonded. 5-Methylsalicyclic acid (8a) forms, in part, an unstable cyclohexadienone (13) resulting from ipso bromine attack.The breakdown of 13 shows intramolecular catalysis by the o-COOH group, which has an effective molarity of 58 M.The microscopic reverse reaction of bromine on the anion 8a must, therefore, involve the o-CO2- group, as suggested above.Implications with respect to the activating effect of hydroxyl groups on cation-forming reactions are discussed.
- Tee, Oswald S.,Iyengar, N. Rani
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p. 4468 - 4473
(2007/10/02)
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- Dibenz[c,e]azepines
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7-Aryl-5H-dibenz[c,e]azepines, e.g., those of the formula STR1 Ar'=phenyl, furyl, thienyl, pyridyl or phenyl subst. by alkyl, OH, alkoxy, halo or CF3 ; R'=halo or CF3 N-oxides or salts thereof are anxiolytic agents.
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