- Enantioselective hydroarylation or hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes
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An efficient protocol for the asymmetric hydroarylation and hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes has been developed. The combination of a rhodium(I) precatalyst and a chiral diene ligand constitutes the catalytic system, which enables the facile synthesis of 2,3-dihydrobenzo[b]thiophene 1,1-dioxides in good yields with high enantioselectivities. The merging of this asymmetric hydroarylation with the downstream alkylations delivers 2,3-dihydrobenzo[b]thiophene 1,1-dioxides that contain two continuous quaternary stereocenters with high enantioselectivities in a diastereodivergent manner.
- Hu, Fangdong,Jia, Jie,Li, Ximing,Xia, Ying
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supporting information
p. 896 - 901
(2021/02/01)
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- Dioxazolones as masked ester surrogates in the Pd(ii)-catalyzed direct C-H arylation of 6,5-fused heterocycles
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A simple and effective Pd(ii)-catalyzed regioselective C(2)-H arylation of 6,5-fused heterocycles with dioxazolones as a masked ester surrogate under mild conditions is reported. The significance of the arylation is highlighted by the new reactivity demonstrated in dioxazolones via proximal C-H activation of the cyclic carbonate of the hydroxamic acid functionality under protic conditions.
- Saxena, Paridhi,Maida, Neha,Kapur, Manmohan
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supporting information
p. 11187 - 11190
(2019/09/30)
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- Nickel-Catalyzed C?S Bond Formation via Decarbonylative Thioetherification of Esters, Amides and Intramolecular Recombination Fragment Coupling of Thioesters
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A nickel catalyzed cross-coupling protocol for the straightforward C?S bond formation has been developed. Various mercaptans and a wide range of ester and amide substrates bearing various substituents were tolerated in this process which afforded products in good to excellent yields. Furthermore, an intramolecular protocol for the synthesis of thioethers starting from thioesters has been developed. The utility of this protocol has been demonstrated in a new synthetic protocol of benzothiophene.
- Lee, Shao-Chi,Liao, Hsuan-Hung,Chatupheeraphat, Adisak,Rueping, Magnus
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supporting information
p. 3608 - 3612
(2018/03/13)
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- C-benzo five-membered heteroaromatic aryl glucoside derivative as well as preparation method and application thereof
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The invention discloses a C-benzo five-membered heteroaromatic aryl glucoside derivative shown in the general formula (I) (in the description), a preparation method of the derivative or an intermediate of the derivative, as well as application of the derivative. In the general formula (I), R, R1, R2, R3, R4, X and Y are defined in the description. The C-benzo five-membered heteroaromatic aryl glucoside derivative is novel in structure, has quite strong inhibitory activity on SGLT-2, has high selection ratio for SGLT-1 and SGLT-2, and can be used for preparing drugs for treating and preventing diseases relevant to SGLT-2.
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Paragraph 0077; 0078
(2016/10/08)
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- METHOD FOR PROMOTING PLANT GROWTH
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The present invention provides a method for promoting plant growth, which comprises treating a plant with a compound represented by the following Formula (1): provided that a method for promoting plant growth which comprises treating plants with a compound corresponding to any one of the following (1) to (8) is excluded: (1) Methyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (2) Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (3) Methyl 6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (4) Methyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (5) Ethyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (6) Ethyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (7) Ethyl 6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, and (8) Ethyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate.
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Paragraph 2116; 2117
(2015/10/28)
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- Construction of polyaromatics via photocyclization of 2-(fur-3-yl) ethenylarenes, using a 3-furyl group as an isopropenyl equivalent synthon
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The construction of different types of substituted arenes was demonstrated through the photocyclization of 2-(fur-3-yl)ethenylarenes using a 3-furyl group as an isopropenyl equivalent synthon in the photocyclization reaction. The furan portion of the photocyclization intermediate could be fragmented via a base-induced elimination reaction to yield a series of substituted polyaromatics, including naphthalene, benzofuran, benzothiophene, phenanthrene, phenalene, acenaphthene, and triphenylene. Using different reagents, this method made it possible to introduce methyl or 2-hydroxyethyl groups as substituents at specific positions in these arenes.
- Chen, Ying-Zhe,Ni, Ching-Wen,Teng, Fu-Lin,Ding, Yi-Shun,Lee, Tunng-Hsien,Ho, Jinn-Hsuan
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p. 1748 - 1762
(2014/03/21)
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- Antitumor agents. 284. new desmosdumotin B analogues with bicyclic B-ring as cytotoxic and antitubulin agents
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We previously reported that the biological acti-vity of analogues of desmosdumotin B (1) was dramatically changed depending on the B-ring system. A naphthalene B-ring analogue 3 exerted potent in vitro activity against a diverse panel of human tumor cell lines with GI50 values of 0.8-2.1 μM. In contrast, 1 analogues with a phenyl B-ring showed unique selective activity against P-glycoprotein (P-gp) overexpressing multidrug resistant cell line. We have now prepared and evaluated 1 analogues with bicyclic or tricyclic aromatic B-ring systems as in vitro inhibitors of human cancer cell line proliferation. Among all synthesized derivatives, 21 with a benzo[b]thiophenyl B-ring was highly active, with GI50 values of 0.06-0.16 μM, and this activity was not influenced by overexpression of P-gp. Furthermore, 21 inhibited tubulin assembly in vitro with an IC50 value of 2.0 μM and colchicine binding by 78% as well as cellular microtubule polymerization and spindle formation.
- Nakagawa-Goto, Kyoko,Wu, Pei-Chi,Lai, Chin-Yu,Hamel, Ernest,Zhu, Hao,Zhang, Liying,Kozaka, Takashi,Ohkoshi, Emika,Goto, Masuo,Bastow, Kenneth F.,Lee, Kuo-Hsiung
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scheme or table
p. 1244 - 1255
(2011/05/07)
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- NOVEL INHIBITORS OF BETA-LACTAMASE
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This invention provides novel β-lactamase inhibitors of the aryl- and heteroarylsulfonamidomethylphosphonate monoester class having nitrogen-based cations or quarternary ammonium groups. The compounds inhibit three classes of β-lactamases and synergize the antibacterial effects of β-lactam antibiotics (e.g., imipenem and ceftazidime) against those micro-organisms normally resistant to the β-lactam antibiotics as a result of the presence of the β-lactamases. Formula (I) or pharmaceutically acceptable salt thereof.
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Page/Page column 22
(2010/12/29)
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- Benzimidazole derivative
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The present invention is a thiobenzimidazole derivative represented by the following formula (1) or a medically acceptable salt thereof wherein said thiobenzimidazole derivative and a medically acceptable salt thereof have a potent activity of inhibiting human chymase. Thus, they are potential preventive and/or therapeutic agents clinically applicable to various diseases in which human chymase is involved.
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- Benzimidazole derivatives
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A benzimidazole derivative or its medically acceptable salt, represented by the following formula (1), that is a human chymase activity inhibitor capable of being applied clinically: 1wherein, R1 and R2 represent a hydrogen atom, an alkyl group or an alkoxy group, etc., A represents an alkylene group or an alkenylene group, E represents —COOR3, —SO3R3, —CONHR3 or —SO2NHR3, etc., G represents an alkylene group, M represents a single bond or —S(O)m. J represents a heterocyclic group, and X represents —CH= or a nitrogen atom.
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- BENZIMIDAZOLE DERIVATIVES
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A benzimidazole derivative or its medically acceptable salt, represented by the following formula (1), that is a human chymase activity inhibitor capable of being applied clinically: wherein, R1 and R2 represent a hydrogen atom, an alkyl group or an alkoxy group, etc., A represents an alkylene group or an alkenylene group, E represents -COOR3, -SO3R3, -CONHR3 or -SO2NHR3, etc., G represents an alkylene group, M represents a single bond or -S(O)m-, J represents a heterocyclic group, and X represents -CH= or a nitrogen atom.
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- Substituted sulfonic acid N-[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds
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The compounds of formula I exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, which are for treating a patient suffering from, or subject to, physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.
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- SUBSTITUTED SULFONIC ACID N-[(AMINOIMINOMETHYL)PHENYLALKYL]-AZAHETEROCYCLAMIDE COMPOUNDS
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The compounds of formula I exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, which are for treating a patient suffering from, or subject to, physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.
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- An improved synthesis of benzo[b]thiophene and its derivatives using modified montmorillonite clay catalysts
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Methods for the preparation of benzothiophene (3) and its derivatives by cyclization of phenylthioacetals (1) over ZnCl2-promoted montmorillonite clay are described. Reactions in solution resulted in only moderate (ca. 50%) yields of 3 and the formation of diphenyl disulfide (4) and uncharacterized products. The production of 4 was explained by coordination of 1 via its oxygen atom to active sites of the catalyst and subsequent bimolecular processes. Good to excellent yields (67-98%) of 3 and its derivatives were obtained using vapor phase techniques at 200-300°C to promote the desired intramolecular cyclizations.
- Clark,Kirk,Yee
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p. 1936 - 1938
(2007/10/02)
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- Substituted imidazoles, pharmaceutical compositions containing these, and the use thereof as antagonists of angiotensin II receptors for the treatment of high blood pressure
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The invention relates to compounds of the formula I STR1 in which X, Y and Z are identical or different and are N or CR 2, R 1 and R 2 are as defined in the description, L is an alkylene radical, q is 0 or 1, and A is the radical of a fused heterobicyclic compound. The invention furthermore relates to a process for preparing the said compounds, agents containing these, and the use thereof in the treatment of high blood pressure.
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- ALKYLATION OF THIOPHENES AND PREPARATION OF BENZOTHIOPHENES USING MODIFIED MONTMORILLONITE CLAY CATALYSTS
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Regioselective benzylation of thiophene and benzothiophene using benzyl chloride and a ZnCl2-promoted montmorillonite catalysts is described.An improved process for the cyclization of (arylthio)acetaldehyde dialkyl acetals to benzothiophenes using the same catalyst is also documented.
- Clark, Peter D.,Kirk, Andrew,Mesher, Shaun T.,Yee, James G.K.
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p. 441 - 444
(2007/10/02)
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- HIGH-TEMPERATURE ORGANIC SYNTHESIS. XLII. REACTION OF HALOGENOARENES AND 2-CHLOROTHIOPHENE WITH HYDROGEN SULFIDE IN THE PRESENCE OF ACETYLENE
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Benzothiophenes are formed with yields of more than 77percent in a single preparative stage during the gas-phase reaction of halogenoarenes with hydrogen sulfide and acetylene (600-700 deg C).It is suggested that arylthiyl radicals (ArS-radical), which are effectively captured by the acetylene, participate in the process.The effect of the structure of the halogenoarene on the selectivity of the process is discussed.The gas-phase reaction of 2-chlorothiophene with hydrogen sulfide in the presence of acetylene leads to the formation of thienothiophene.
- Deryagina, E. N.,Korchevin, N. A.,Sukhomazova, E. N.,Russavskaya, N. V.,Voronkov, M. G.
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p. 1863 - 1867
(2007/10/02)
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- Synthesis of Substituted Benzothiophenes by Acid-Catalyzed Cyclization of Thiophenylacetals and Ketones
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Benzothiophenes substituted at the 3 position with methyl or carboxymethyl and at the 5 position with methyl, methoxy, chloro, bromo and nitro were prepared by cyclization of thiophenyl-acetals and ketones using a suspension of polyphosphoric acid in refluxing chlorobenzene.The overall efficiency of this method is superior to literature procedures because of the lower temperature and the limited amount of PPA used.
- Ple, Patrick A.,Marnett, Lawrence J.
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p. 1271 - 1272
(2007/10/02)
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- Pyridyl-substituted benzothiophenes
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The present invention provides novel pyridinyl-benzothiophenes and derivatives thereof which are useful as thromboxane A2 (TXA2) synthetase inhibitors and as such represent potent pharmacological agents.
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- Thermolysis of Thiophenedicarboxylic Acid Anhydrides as a Route to Five-Membered Hetarynes
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Flow vacuum thermolysis (FVT) of the anhydrides of thiophene-2,3- (5) and -3,4-dicarboxylic acid (6) and of thianaphthene-2,3-dicarboxylic acid (7) in the presence of thiophene, 1,3-cyclohexadiene, or benzene gave thianthrene (15a), presumably by aromatization of an intermadiate Diels-Alder adduct of the diene traps and the aryne 2,3-didehydrothiophene (8).A similar rationale explains the formation of dibenzothiophene from 7 and thiophene, the four monomethylthianaphthenes 22-25 from 5 and cyclopentadiene, 5,6-dimethylthianaphthene (15f) from 5 and 2,3-dimethylbutadiene, and a mixture of hydroxythianaphthenes (15d) from 5 and furan.The latter reaction also produces a mixture of isomeric cyclopentanothiophenes (19) which probably arise by decarbonylation of 15d.An FVT reaction of 5 with propyne as the trap gave a mixture of allenyl-(28) and propynylthiophenes 29 which probably arise by an ene reaction of the trap and the aryne 8.Decomposition of the anhydrides 5 and 6 in molten anthracene led only to Friedel-Crafts products such as thienylanthracenes 33 and quinones 34 from 5 and 39 and 40 from 6.The diene reactivity of thiophene 13a in the gas phase was demonstrated by the formation of naphthalene from its reaction with benzyne generated from the thermolysis of indanetrione and by the formation of indene from 13a plus cyclopentadiene.Possible, but improbable, interpretations of the FVT results without invoking a five-membered hetaryne intermediate are considered.
- Reinecke, Manfred G.,Newsom, James G.,Chen, Lao-Jer
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p. 2760 - 2769
(2007/10/02)
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