- Method for preparing 2-chlorobenzoxazole and 2,6-dichlorobenzoxazole from o-aminophenol by taking solid triphosgene as chlorinating agent
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The invention provides a method for preparing 2-chlorobenzoxazole and 2,6-dichlorobenzoxazole from o-aminophenol by taking solid triphosgene as a chlorinating agent. The method comprises the followingsteps: step 1, respectively preparing 2-benzoxazolone and 2-mercapto benzoxazole by taking the o-aminophenol as a raw material; step 2, preparing the 2-chlorobenzoxazole by taking the 2-mercapto benzoxazole as a raw material and the solid triphosgene as the chlorinating agent; step 3, preparing 6-chlorobenzoxazolone by taking TCCA and the 2-benzoxazolone as raw materials; step 4, preparing 2-mercapto-6-chlorobenzoxazole; step 5, preparing the 2,6-dichlorobenzoxazole by taking the 2-mercapto-6-chlorobenzoxazole as a raw material and the solid triphosgene as the chlorinating agent. The method provided by the invention is a brand-new preparation method, which has the advantages of less corrosion to equipment, high yield, less reaction time, mild reaction conditions, less by-products and reduced environmental pollution.
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Paragraph 0028-0030
(2018/12/05)
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- Novel benzoxazole derivatives featuring rhodanine and analogs as antihypergycemic agents: synthesis, molecular docking, and biological studies
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A novel series of benzoxazolyl linked benzylidene based rhodanine and their cyclic analogs were synthesized, characterized and evaluated for their α-amyloglucosidase inhibitory activity. Out of eight target compounds, two compounds (4b and 5b) displayed potent inhibitory activity against α-amyloglucosidase with IC50 values in the range of 0.24 ± 0.01–0.94 ± 0.01 μM as compared to standard drug acarbose. Among all the tested compounds, compound 5b containing rhodanine at 3-position of phenyl was found to be the most active inhibitor of α-amyloglucosidase. Docking studies showed the existence of potential H-bonding interactions between synthesized compounds and α-glucosidase which might be responsible for good biological activity.
- Singh, Varinder,Singh, Amanjot,Singh, Gagandeep,Verma, Raman K.,Mall, Rajiv
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p. 735 - 743
(2017/10/25)
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- Method for preparing halogenated (hetero) aromatic hydrocarbons
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The invention relates to a method for preparing halogenated (hetero) aromatic hydrocarbons. The halogenated (hetero) aromatic hydrocarbons are prepared from cheap and easily available perfluorobutyl iodide, carbon tetrabromide and carbon tetrachloride as iodinated, brominated and chlorinated reagents respectively under the action of alkali catalysis (promotion). The method comprises the following steps: firstly, (hetero) aromatic hydrocarbons, a halogenated reagent and an inorganic base are placed in an organic solvent, stirred at room temperature and monitored with TLC until a substrate disappears, and the reaction is stopped; then, a reaction mixed solution is poured into water and extracted, an organic phase is dried, and the organic solvent is removed under reduced pressure; finally, silica-gel column chromatography is performed on a crude product, and a product is obtained. Purification can also be performed by recrystallization. The method has the advantages that the synthetic route is wide in substrate range, raw materials and reagents are cheap and easily available, operation is simple, conditions are mild, yield is high, energy consumption is reduced, the reaction route is safe, gram-grade preparation can be performed and the like.
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Paragraph 0065; 0066
(2018/03/24)
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- OCTAHYDROPYRROLO [3, 4-c] PYRROLE DERIVATIVES AND USES THEREOF
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The invention relates to octahydropyrrolo [3, 4-c] pyrrole derivatives and uses thereof. Compounds and pharmaceutical compositions comprising the compounds provided herein are used for antagonizing orexin receptors. The invention also relates to processes for preparing the compounds and pharmaceutical compositions, and uses thereof in treating or preventing a disease related to orexin receptors.
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Paragraph 00210
(2017/07/04)
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- Efficient transposition of the sandmeyer reaction from batch to continuous process
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The transposition of Sandmeyer chlorination from a batch to a safe continuous-flow process was investigated. Our initial approach was to develop a cascade method using flow chemistry which involved the generation of a diazonium salt and its quenching with copper chloride. To achieve this safe continuous process diazotation, a chemometric approach (Simplex method) was used and extrapolated to establish a fully continuous-flow method. The reaction scope was also examined via the synthesis of several (het)aryl chlorides. Validation and scale-up of the process were also performed. A higher productivity was obtained with increased safety.
- D'Attoma, Joseph,Camara, Titi,Brun, Pierre Louis,Robin, Yves,Bostyn, Stéphane,Buron, Frédéric,Routier, Sylvain
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- Synthesis, biological evaluation and molecular docking study of N-arylbenzo[d]oxazol-2-amines as potential α-glucosidase inhibitors
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A novel series of N-arylbenzo[d]oxazol-2-amines (4a–4m) were synthesized and evaluated for their α-glucosidase inhibitory activity. Compounds 4f–4i, 4k and 4m displayed potent inhibitory activity against α-glucosidase with IC50values in the range of 32.49?±?0.17–120.24?±?0.51?μM as compared to the standard drug acarbose. Among all tested compounds, compound 4g having 4-phenoxy substitution at the phenyl ring was found to be the most active inhibitor of α-glucosidase with an IC50value of 32.49?±?0.17?μM. Analysis of the kinetics of enzyme inhibition indicated that compound 4g is a noncompetitive inhibitor of α-glucosidase with a Kivalue of 31.33?μM. Binding interaction of compound 4g with α-glucosidase was explored by molecular docking simulation.
- Wang, Guangcheng,Peng, Zhiyun,Wang, Jing,Li, Juan,Li, Xin
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p. 5374 - 5379
(2016/10/22)
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- A convenient one-pot synthesis of N-substituted 2-aminoazole derivatives
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A practical protocol for the one-pot synthesis of N-substituted 2-aminoazole derivatives is described, employing simple azole substrates, nitrogen nucleophiles, lithium tert-butoxide as the base, and iodine to mediate carbon-nitrogen bond formation. This method proceeds at room temperature under an air atmosphere using a normal benchtop set-up, or can be performed conveniently using microwave irradiation. Georg Thieme Verlag Stuttgart - New York.
- Yotphan, Sirilata,Beukeaw, Danupat,Reutrakul, Vichai
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supporting information
p. 936 - 942
(2013/05/09)
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- Synthesis and insecticidal activity of novel dihalopropene derivatives containing benzoxazole moiety: A structure-activity relationship study
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Ten dichloropropene derivatives containing benzoxazole moiety were synthesized and bioassayed in order to determine their in vivo insecticidal activity. The structures of obtained compounds were identified by 1H NMR, MS and elemental analyses. The bioassay results indicated that compound 2-(3-(2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy)propoxy)-5-(trifluoromethyl) benzo[d]oxazole (5i, R1 is trifluoromethyl, R2 is H and n is 3) had the optimal structure with best insecticidal activity against Spodoptera exigua (100%) at 1 mg/L concentration, highlighting the importance of trifluoromethyl group. The structure-activity relationship of the synthesized compounds was discussed as well.
- Guan, Aiying,Qin, Yukun,Wang, Junfeng,Li, Bin
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p. 120 - 123
(2013/11/06)
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- Synthesis of new chiral ferrocenyl P,N-ligands with a benzoxazole ring and their application in Ag-catalyzed asymmetric [3+2] cycloaddition
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New chiral ferrocenyl P,N-ligands with a benzoxazole ring as the N-donor group have been synthesized from 2-aminophenol through a three-step transformation and successfully employed in the Ag-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with electron-deficient alkenes. High diastereoselectivities, excellent enantioselectivities, and good yields have been achieved for a variety of substrates, demonstrating the potential of these new P,N-ligands in asymmetric catalysis.
- Yan, Sheng,Zhang, Cheng,Wang, Ya-Hui,Cao, Zhong,Zheng, Zhuo,Hu, Xiang-Ping
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p. 3669 - 3672
(2013/07/11)
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- Preparation, antibacterial evaluation and preliminary structure-activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives
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In this study, a novel benzothiazol- and benzooxazol-2-amine scaffold with antibacterial activity was designed and synthesized. Preliminary structure-activity relationship analysis displayed that compound 8t with a 5,6-difluorosubstituted benzothiazole was found to be a potent inhibitor of Gram-positive pathogens, and exhibited some potential against drug-resistant bacteria and without cytotoxicity in therapeutic concentrations. In addition, molecular docking studies indicated that Staphylococcus aureus methionyl-tRNA synthetase might be the possible target of these compounds. Taken together, the present study provides an effective entry to the synthesis of a good lead for subsequent optimization and a new small molecule candidate drug for antibacterial therapeutics.
- Ouyang, Liang,Huang, Yuhui,Zhao, Yuwei,He, Gu,Xie, Yongmei,Liu, Jie,He, Jun,Liu, Bo,Wei, Yuquan
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supporting information; experimental part
p. 3044 - 3049
(2012/06/04)
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- CsF-Celite catalyzed facile N-alkylation of 2(3H)-benzoxazolones and antimicrobial properties of 2-substituted benzoxazole and 3-substituted-2(3H)- benzoxazolone derivatives
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The synthesis and antimicrobial activity studies of a new series of cyclic amine containing benzoxazoles and benzoxazolone-2(3H)-ones derivatives were described. The alkylation of benzoxazolone was carried out using cesium fluoride-Celite. The newly synthesized compounds with the influence of the induction of the cyclic amine moiety in the benzoxazole scaffold have been evaluated with respect to the antibacterial and antifungal activity. The 2-cyclic amine-1,3-benzoxazoles (5a-l), 5-chloro-3-alkyl substituted-1,3- benzoxazol-2(3H)-ones (8a-f), and 3-[3- (cyclic amine)propyl]-1,3-benzoxazol- 2(3H)-ones (9a-f) were synthesized. These derivatives were tested for antibacterial and antifungal activity. Among the compounds tested, 8c and 9f showed moderate to good antibacterial and antifungal activity. Compound 8a showed good antifungal activity. Springer Science+Business Media, LLC 2010.
- Murty,Ram, Kesur R.,Rao, Rayudu Venkateswara,Yadav,Murty,Kumar, K. Pranay
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scheme or table
p. 626 - 636
(2012/04/04)
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- Synthesis and preliminary evaluation of 2-substituted-1,3-benzoxazole and 3-[(3-substituted)propyl]-1,3-benzoxazol-2(3H)-one derivatives as potent anticancer agents
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The synthesis and cytotoxic activity studies of a new series of cyclic amine containing benzoxazole and benzoxazolone derivatives are described. The 2-cyclic amine-1,3-benzoxazoles 5a-k, 5-chloro-3-(3-chloropropyl)- 1,3-benzoxazol-2(3H)-one 8 and 3-[3-(cyclic amino)- propyl]-1,3-benzoxazol-2(3H) -ones 9a-f were synthesized. The newly synthesized compounds with the influence of the presence of cyclic amine moiety in the benzoxazole scaffold have been evaluated with respect to their cytotoxic effect toward four human cancer cell lines. The new compounds were evaluated to see whether substitution at the second and third position of the benzoxazole motif influence their cytotoxic effect toward cancer cells. Springer Science+Business Media, LLC 2011.
- Murty,Ram, Kesur R.,Rao, Rayudu Venkateswara,Yadav,Rao, Janapala Venkateswara,Cheriyan, Vino T.,Anto, Ruby John
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scheme or table
p. 576 - 586
(2012/04/04)
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- NOVEL MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS REPLICATION
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The embodiments provide compounds of the general Formulae I, II, III, IV, V, VI, VII, and X, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.
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- Design and synthesis of highly potent and selective human peroxisome proliferator-activated receptor α agonists
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A combination of benzoxazole, phenoxyalkyl side chain, and phenoxybutyric acids was identified as a highly potent and selective human peroxisome proliferator-activated receptor α (PPARα) agonist. The synthesis, structure-activity relationship (SAR) studies, and in vivo activities of the representative compounds are described.
- Yamazaki, Yukiyoshi,Abe, Kazutoyo,Toma, Tsutomu,Nishikawa, Masahiro,Ozawa, Hidefumi,Okuda, Ayumu,Araki, Takaaki,Oda, Soichi,Inoue, Keisuke,Shibuya, Kimiyuki,Staels, Bart,Fruchart, Jean-Charles
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p. 4689 - 4693
(2008/02/11)
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- A convenient preparation of heteroaryl sulfonamides and sulfonyl fluorides from heteroaryl thiols
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Heteroaromatic thiols may be oxidized to the sulfonyl chloride at low temperature (-25 °C) by using 3.3 equiv of aqueous sodium hypochlorite. The reaction is rapid, avoids the use of chlorine gas, and succeeds with substrates that have previously been found to afford little or none of the sulfonamide product with other procedures. The method allows the preparation of the sulfonyl fluorides, which are stable enough to be purified and stored, making them potentially useful monomers in parallel chemistry efforts.
- Wright, Stephen W.,Hallstrom, Kelly N.
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p. 1080 - 1084
(2007/10/03)
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- Synthesis and evaluation of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 3: Heterocyclic P3
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A series of Nα-2-benzoxazolyl-α-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure-activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound 3 bound to the active site of cathepsin S is also reported.
- Tully, David C.,Liu, Hong,Alper, Phil B.,Chatterjee, Arnab K.,Epple, Robert,Roberts, Michael J.,Williams, Jennifer A.,Nguyen, Khanhlinh T.,Woodmansee, David H.,Tumanut, Christine,Li, Jun,Spraggon, Glen,Chang, Jonathan,Tuntland, Tove,Harris, Jennifer L.,Karanewsky, Donald S.
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p. 1975 - 1980
(2007/10/03)
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- Method for producing chlorobenzoxazolene
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The invention relates to a process for preparing chlorobenzoxazoles of the formula (I), in which R1, R2 and R4 are as defined in claim 1 andin case (a) R3=H, halogen, CN, NO2, C1-C5-alkyl, C1-C5-alkoxy, aryl or aryloxy, where each of the 4 lastmentioned radicals is unsubstituted or substituted, orin case (b) R3=chlorine,which comprises reacting benzoxazoles of the formula (II), in which R1, R2 and R4 are as defined in formula (I) and R3 in case (a) is as defined in formula (I) and R3 in case (b) is hydrogen,in the presence of an acidic catalyst with a chlorinating agent to give the monochlorination product (I) or in case (b) with an excess of the chlorinating agent to give the dichlorination product (I) in which R3=chlorine.
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- Synthesis of N-(thio)phosphoryl-N′-2-benzoxazolyl semicarbazides
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We prepared the benzoxazole derivatives bearing the (thio) phosphoryl moiety by addition reactions of 2-hydrazionbenzoxazole with isothiocyanato (thio) phosphates and characterized their structures by elementary analysis and 1H NMR and IR spectral data. From the results of biological activity screening, we found that these compounds possess some herbicidal, and plant growth regulator activities, and especially good fungicidal activity against Puccinia recondita.
- Chen, Wen-Bin,Jin, Gui-Yu
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p. 151 - 155
(2007/10/03)
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- Substituted 3-(2-Benzoxazyl)-benzimidazol-2-(1H)-ones: A new class of GABA(A) brain receptor ligands
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A novel class of potent benzodiazepine receptor (BZR) ligands has been designed and synthesized aided by molecular modeling of known benzodiazepine ligands such as CGS-8216 and the use of known pharmacophore models. (C) 2000 Elsevier Science Ltd.
- DeSimone, Robert W.,Blum, Charles A.
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p. 2723 - 2726
(2007/10/03)
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- A new synthesis of chloroheterocycles via metal-halogen exchange between trichloroacetyl derivatives and heteroaromatic lithium and Grignard reagents
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The reaction between 2-lithio derivatives of aromatic azaheterocycles and trichlorocetyl derivatives rapidly produces the corresponding 2-chloro derivatives in high yields through a metal-halogen exchange mechanism. The use of ethyl trichloroacetate can give better results with respect to those obtained with trichloroacetyl chloride, which probably involves dichloroketene formation. The reaction with Grignard reagents is more complex: in fact, 2-benzothiazolylmagnesium chloride with ethyl trichloroacetate or trichloroacetyl chloride gives 2-chlorobenzothiazole together with considerable amounts of ethyl 1,3-benzothiazole-2-carboxylate or 2-benzothiazolyl dichloromethyl ketone, respectively.
- Boga, Carla,Del Vecchio, Erminia,Forlani, Luciano,Milanesi, Lilia,Edgardo Todesco, Paolo
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p. 155 - 159
(2007/10/03)
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- Benzoxazolamines and Benzothiazolamines: Potent, Enantioselective Inhibitors of Leukotriene Biosynthesis with a Novel Mechanism of Action
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A series of benzoxazolamine and benzothiazolamine analogs that inhibit leukotriene (LT) biosynthesis are described.The initial lead, (S)-N-(benzothiazol-2-yl)phenylalanine ethyl ester (5a), was discovered in a screening program for inhibition of Ca-ionophore-A23187-induced LTB4 release in human polymorphonuclear leukocytes (IC50 0.23 μM).Through structural modification, it was determined that hydrophobic substituents in the 5-position and replacement of the phenyl ring of phenylalanine with a cyclohexyl group greatly enhance potency.Several ester bioisosteres that retain potency and enantiomeric selectivity are described.Lead optimization culminated in (S)-N--5-methyl-2-benzoxazolamine (43b), IC50 0.001 μM.The compounds described are not inhibitors of 5-lipoxygenase but, rather, act at the level of arachidonic acid release.
- Lazer, Edward S.,Miao, Clara K.,Wong, Hin-Chor,Sorcek, Ronald,Spero, Denice M.,et al.
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p. 913 - 923
(2007/10/02)
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- 3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives: Inhibitors of immune complex induced inflammation
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3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives were evaluated in the dermal and pleural reverse passive Arthus reactions in the rat. In the pleural test these compounds were effective in reducing exudate volume and accumulation of white blood cells. This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin. The structural requirements for inhibiting the Arthus reactions were studied by systematic chemical modification of 1. These structure-activity relationship studies revealed that nitrogen 1' of the hydrazino group is essential for activity and must be electron rich, whereas chemical modifications of other sites of 1 had only a modest effect on activity.
- Haviv,Ratajczyk,DeNet,Kerdesky,Walters,Schmidt,Holms,Young,Carter
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p. 1719 - 1728
(2007/10/02)
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- Substituted phenoxyalkanecarboxylic acid esters used to combat weeds in rice fields
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Novel substituted phenoxyalkanecarboxylic acid esters of the formula STR1 in which R1 and R2, independently of one another, are a hydrogen atom, a halogen atom, a lower alkyl group or a nitro group, or R1 and R2, together with the benzene ring to which they are bonded, are a naphthalene ring, R3 and R4, independently of one another, are a hydrogen atom or a methyl group, n is 1 or 2, m is 0 or 1, X is an oxygen atom, a sulfur atom, a sulfonyl group or a group of the formula STR2 in which R6 is a lower alkyl group, R5 is a hydrogen atom or a halogen atom, and Y is an oxygen atom or a sulfur atom, and the use of the new compounds as herbicides.
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- CROSS-COUPLING OF 2-CHLOROBENZOXAZOLE WITH β,γ-UNSATURATED GRIGNARD REAGENTS: REGIOSELECTIVE SYNTHESIS OF 2-ALLYL-, 2-ALLENYL-, AND 2-PROPARGYL-BENZOXAZOLES.
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β,γ-unsaturated Grignard reagents react regioselectively with 2-chlorobenzoxazole to give high to excellent yields of 2-allyl-, 2-allenyl-, and 2-propargyl-bezoxazoles.Reduction of allylbenzoxazoles leads to quantitative yields of branched 2-alkylbenzoxazoles.
- Babudri, Francesco,Florio, Saverio,Ronzini, Ludovico
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p. 3905 - 3912
(2007/10/02)
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- Process for preparing 2-chlorobenzoxazoles
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In the process for preparing 2-chlorobenzoxazoles of the formula STR1 wherein each of R1, R2, R3 and R4 is independently of one another, H, chloro or alkyl having 1 to 4 carbon atoms, which comprises reacting chlorine with 2-mercaptobenzoxazoles of the formula STR2 wherein the improvement comprises providing a melt of previously prepared 2-chloro-benzoxazole, adding the 2-mercaptobenzoxazole reactant to the 2-chlorobenzoxazole melt and simultaneously or subsequently passing chlorine into the melt, with the proviso that substituents R1 to R4 are identical in both the 2-chlorobenzoxazole melt and the 2-mercaptobenzoxazole reactant.
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