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Vishnu K Tandon - One of the best experts on this subject based on the ideXlab platform.
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Strategy to Construct Stair‐Shaped Partially Reduced Naphtho[1,2‐b]pyrano[2,3‐d]Oxepines and Dinaphtho[1,2‐b,d]Oxepines
Journal of Heterocyclic Chemistry, 2016Co-Authors: Sanjay K Gautam, Hardesh K Maurya, Ramendra Pratap, Abhinav Kumar, Vishnu K TandonAbstract:A concise and efficient base-induced synthesis of stair-shaped, 4-methylthio-2-oxo-5,6-dihydro-2H-naphtho[1,2-b]pyran[2,3-d]Oxepine-3-carbonitriles () has been delineated by the reaction of 3,4-dihydronaphtho[1,2-b]Oxepin-5(2H)-one () and methyl 2-cyano-3,3-dimethylthioacrylate in DMSO using powdered KOH as a base at room temperature. Amination of has been achieved by reaction with secondary amine in ethanol at reflux temperature to yield 4-sec-amino-2-oxo-5,6-dihydro-2H-naphtho[1,2-b]pyran[2,3-d]Oxepine-3-carbonitriles (). Reaction of with aryl methyl ketone () in DMSO at room temperature using powdered KOH as a base produced stair-shaped 5-aryl-7,8-dihydro-1,4-dioxa-2,3-dioxodinaphtho[1,2-b,d]Oxepine () in good yields. However, reaction of 6-aryl-2H-pyran-2-one-3-carbonitrile () with 3,4-dihydronaphtho[1,2-b]Oxepin-5(2H)-one () did not give similar product, but in lieu 4-aryl-5,6-dihydronaphtho[1,2-b]Oxepino[4,5-b]pyran-2-ylidene)acetonitrile () was isolated and characterized.
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strategy to construct stair shaped partially reduced naphtho 1 2 b pyrano 2 3 d Oxepines and dinaphtho 1 2 b d Oxepines
Journal of Heterocyclic Chemistry, 2016Co-Authors: Sanjay K Gautam, Hardesh K Maurya, Ramendra Pratap, Abhinav Kumar, Vishnu K TandonAbstract:A concise and efficient base-induced synthesis of stair-shaped, 4-methylthio-2-oxo-5,6-dihydro-2H-naphtho[1,2-b]pyran[2,3-d]Oxepine-3-carbonitriles () has been delineated by the reaction of 3,4-dihydronaphtho[1,2-b]Oxepin-5(2H)-one () and methyl 2-cyano-3,3-dimethylthioacrylate in DMSO using powdered KOH as a base at room temperature. Amination of has been achieved by reaction with secondary amine in ethanol at reflux temperature to yield 4-sec-amino-2-oxo-5,6-dihydro-2H-naphtho[1,2-b]pyran[2,3-d]Oxepine-3-carbonitriles (). Reaction of with aryl methyl ketone () in DMSO at room temperature using powdered KOH as a base produced stair-shaped 5-aryl-7,8-dihydro-1,4-dioxa-2,3-dioxodinaphtho[1,2-b,d]Oxepine () in good yields. However, reaction of 6-aryl-2H-pyran-2-one-3-carbonitrile () with 3,4-dihydronaphtho[1,2-b]Oxepin-5(2H)-one () did not give similar product, but in lieu 4-aryl-5,6-dihydronaphtho[1,2-b]Oxepino[4,5-b]pyran-2-ylidene)acetonitrile () was isolated and characterized.
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an expeditious concise synthesisof benzo b pyrano 2 3 d Oxepines and dibenzo b d Oxepines
Synlett, 2009Co-Authors: Vishnu K Tandon, Hardesh K Maurya, Balendu KumarAbstract:An efficient concise synthesis of 4-methylthio-2-oxo-5,6-dihydro-2 H-benzo[ B]pyrano[2,3- D]Oxepine-3-carbonitriles has beendelineated through condensation-cyclization of 3,4-dihydro-2 H-benzo[ B]Oxepin-5(2 H)-ones and methyl 2-cyano-3,3-dimethylthioacrylatein DMF using powdered KOH as a base. A base--induced reactionof 3,4-dihydro-2 H-benzo[ B]Oxepin-5(2 H)-ones and6-aryl-4-methylthio-2 H-pyran-2-one-3-carbonitrilein the presence of powdered KOH in DMF gave an isomeric mixtureof ( E)- and ( Z)-2-(4-phenyl-5,6-dihydro-2 H-benzo[ B]pyrano[2,3- D]Oxepin-2-ylidene)acetonitriles.However, the ring transformation of 6-aryl-4-(s EC-amino)-2 H-pyran-2-one-3-carbonitriles from 3,4-dihydro-2 H-benzo[ B]Oxepin-5(2 H)-ones under analogous reaction conditionsexclusively gave 8-phenyl-10-( SEC-amino)-6,7-dihydrodibenzo[ B, D]Oxepine-11-carbonitriles.
Hardesh K Maurya - One of the best experts on this subject based on the ideXlab platform.
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Strategy to Construct Stair‐Shaped Partially Reduced Naphtho[1,2‐b]pyrano[2,3‐d]Oxepines and Dinaphtho[1,2‐b,d]Oxepines
Journal of Heterocyclic Chemistry, 2016Co-Authors: Sanjay K Gautam, Hardesh K Maurya, Ramendra Pratap, Abhinav Kumar, Vishnu K TandonAbstract:A concise and efficient base-induced synthesis of stair-shaped, 4-methylthio-2-oxo-5,6-dihydro-2H-naphtho[1,2-b]pyran[2,3-d]Oxepine-3-carbonitriles () has been delineated by the reaction of 3,4-dihydronaphtho[1,2-b]Oxepin-5(2H)-one () and methyl 2-cyano-3,3-dimethylthioacrylate in DMSO using powdered KOH as a base at room temperature. Amination of has been achieved by reaction with secondary amine in ethanol at reflux temperature to yield 4-sec-amino-2-oxo-5,6-dihydro-2H-naphtho[1,2-b]pyran[2,3-d]Oxepine-3-carbonitriles (). Reaction of with aryl methyl ketone () in DMSO at room temperature using powdered KOH as a base produced stair-shaped 5-aryl-7,8-dihydro-1,4-dioxa-2,3-dioxodinaphtho[1,2-b,d]Oxepine () in good yields. However, reaction of 6-aryl-2H-pyran-2-one-3-carbonitrile () with 3,4-dihydronaphtho[1,2-b]Oxepin-5(2H)-one () did not give similar product, but in lieu 4-aryl-5,6-dihydronaphtho[1,2-b]Oxepino[4,5-b]pyran-2-ylidene)acetonitrile () was isolated and characterized.
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strategy to construct stair shaped partially reduced naphtho 1 2 b pyrano 2 3 d Oxepines and dinaphtho 1 2 b d Oxepines
Journal of Heterocyclic Chemistry, 2016Co-Authors: Sanjay K Gautam, Hardesh K Maurya, Ramendra Pratap, Abhinav Kumar, Vishnu K TandonAbstract:A concise and efficient base-induced synthesis of stair-shaped, 4-methylthio-2-oxo-5,6-dihydro-2H-naphtho[1,2-b]pyran[2,3-d]Oxepine-3-carbonitriles () has been delineated by the reaction of 3,4-dihydronaphtho[1,2-b]Oxepin-5(2H)-one () and methyl 2-cyano-3,3-dimethylthioacrylate in DMSO using powdered KOH as a base at room temperature. Amination of has been achieved by reaction with secondary amine in ethanol at reflux temperature to yield 4-sec-amino-2-oxo-5,6-dihydro-2H-naphtho[1,2-b]pyran[2,3-d]Oxepine-3-carbonitriles (). Reaction of with aryl methyl ketone () in DMSO at room temperature using powdered KOH as a base produced stair-shaped 5-aryl-7,8-dihydro-1,4-dioxa-2,3-dioxodinaphtho[1,2-b,d]Oxepine () in good yields. However, reaction of 6-aryl-2H-pyran-2-one-3-carbonitrile () with 3,4-dihydronaphtho[1,2-b]Oxepin-5(2H)-one () did not give similar product, but in lieu 4-aryl-5,6-dihydronaphtho[1,2-b]Oxepino[4,5-b]pyran-2-ylidene)acetonitrile () was isolated and characterized.
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an expeditious concise synthesisof benzo b pyrano 2 3 d Oxepines and dibenzo b d Oxepines
Synlett, 2009Co-Authors: Vishnu K Tandon, Hardesh K Maurya, Balendu KumarAbstract:An efficient concise synthesis of 4-methylthio-2-oxo-5,6-dihydro-2 H-benzo[ B]pyrano[2,3- D]Oxepine-3-carbonitriles has beendelineated through condensation-cyclization of 3,4-dihydro-2 H-benzo[ B]Oxepin-5(2 H)-ones and methyl 2-cyano-3,3-dimethylthioacrylatein DMF using powdered KOH as a base. A base--induced reactionof 3,4-dihydro-2 H-benzo[ B]Oxepin-5(2 H)-ones and6-aryl-4-methylthio-2 H-pyran-2-one-3-carbonitrilein the presence of powdered KOH in DMF gave an isomeric mixtureof ( E)- and ( Z)-2-(4-phenyl-5,6-dihydro-2 H-benzo[ B]pyrano[2,3- D]Oxepin-2-ylidene)acetonitriles.However, the ring transformation of 6-aryl-4-(s EC-amino)-2 H-pyran-2-one-3-carbonitriles from 3,4-dihydro-2 H-benzo[ B]Oxepin-5(2 H)-ones under analogous reaction conditionsexclusively gave 8-phenyl-10-( SEC-amino)-6,7-dihydrodibenzo[ B, D]Oxepine-11-carbonitriles.
Kazuhiro Kubo - One of the best experts on this subject based on the ideXlab platform.
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Inhibitors of Acyl-CoA:Cholesterol Acyltransferase. 1. Synthesis and Hypocholesterolemic Activity of Dibenz[b,e]Oxepin-11-carboxanilides
Journal of medicinal chemistry, 1994Co-Authors: Toshiaki Kumazawa, Hiroyuki Obase, Shiro Shirakura, Kazuhiro Kubo, Masashi Yanase, Hiroyuki Harakawa, Eiko Ohishi, Shoji Oda, Koji YamadaAbstract:A series of N-phenyl-6,11-dihydrodibenz[b,e]Oxepin-11-carboxamides and related derivatives were prepared on the basis of structures of the reported inhibitors of acyl-CoA:cholesterol acyltransferase (ACAT). These compounds were tested for their ability to inhibit ACAT (liver microsomes from cholesterol-fed rabbits) in vitro and to decrease serum total cholesterol in cholesterol-fed golden hamsters in vivo. The structure-activity relationships in vitro were as follows. Substitution at positions 2 and 6 in the anilide resulted in potent inhibitory activity, and the potency increased with increasing size of the substituents, with maximum potency being obtained with a 2,6-diisopropyl substitution. The position of the substituent on the dibenz[b,e]Oxepin ring system influenced the activity, and substitution at position 2 was critical for potent activity. The electronic effect of the substituent at position 2 does not influence activity, but bulkiness seems to be a significant factor. The lipophilicity of the compounds also plays an important role in determining ACAT inhibitory activity. Among the compounds tested, 2-bromo-N-(2,6-diisopropylphenyl)-6,11-dihydrodibenz-[b,e]++ +Oxepin-11- carboxamide (33, KF17828) showed significant in vitro activity (rabbit liver microsomes IC50 = 23 nM) and the most potent in vivo activity (complete reduction in elevated serum total cholesterol levels at a dose of 10 mg/kg in hamsters).
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DibenzOxepin derivatives: thromboxane A2 synthase inhibition and thromboxane A2 receptor antagonism combined in one molecule.
Journal of medicinal chemistry, 1993Co-Authors: Etsuo Ohshima, Hideyuki Sato, Hiroyuki Obase, Ichiro Miki, Akio Ishii, Michiyo Kawakage, Shiro Shirakura, Akira Karasawa, Kazuhiro KuboAbstract:A new series of 6,11-dihydrodibenz[b,e]Oxepin derivatives exerting both thromboxane synthase inhibitory (TXS-I) and thromboxane receptor antagonist (TXRA) activities is described. (-)-11-[(3-Pyridylmethyl)thio]-6,11-dihydrodibenz[b,e]Oxepin -2- carboxylic acid [(-)-3] and (E)-11-[2-(3-pyridyl)ethylidene]-6,11-dihydrodibenz[b,e]Oxepin+ ++-2- carboxylic acid methanesulfonate (11E) exhibited potent inhibitory effects on bovine platelet thromboxane synthase with IC50 values of 4.0 and 14 nM, respectively, and these derivatives also antagonized guinea pig platelet TXA2/PGH2 receptors with Ki values of 85 and 180 nM, respectively. Compound 11E exhibited the dual inhibitory activity in ex vivo experiments and demonstrated a significant protective effect in a rat acute renal failure model.
Hiroyuki Obase - One of the best experts on this subject based on the ideXlab platform.
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Inhibitors of Acyl-CoA:Cholesterol Acyltransferase. 1. Synthesis and Hypocholesterolemic Activity of Dibenz[b,e]Oxepin-11-carboxanilides
Journal of medicinal chemistry, 1994Co-Authors: Toshiaki Kumazawa, Hiroyuki Obase, Shiro Shirakura, Kazuhiro Kubo, Masashi Yanase, Hiroyuki Harakawa, Eiko Ohishi, Shoji Oda, Koji YamadaAbstract:A series of N-phenyl-6,11-dihydrodibenz[b,e]Oxepin-11-carboxamides and related derivatives were prepared on the basis of structures of the reported inhibitors of acyl-CoA:cholesterol acyltransferase (ACAT). These compounds were tested for their ability to inhibit ACAT (liver microsomes from cholesterol-fed rabbits) in vitro and to decrease serum total cholesterol in cholesterol-fed golden hamsters in vivo. The structure-activity relationships in vitro were as follows. Substitution at positions 2 and 6 in the anilide resulted in potent inhibitory activity, and the potency increased with increasing size of the substituents, with maximum potency being obtained with a 2,6-diisopropyl substitution. The position of the substituent on the dibenz[b,e]Oxepin ring system influenced the activity, and substitution at position 2 was critical for potent activity. The electronic effect of the substituent at position 2 does not influence activity, but bulkiness seems to be a significant factor. The lipophilicity of the compounds also plays an important role in determining ACAT inhibitory activity. Among the compounds tested, 2-bromo-N-(2,6-diisopropylphenyl)-6,11-dihydrodibenz-[b,e]++ +Oxepin-11- carboxamide (33, KF17828) showed significant in vitro activity (rabbit liver microsomes IC50 = 23 nM) and the most potent in vivo activity (complete reduction in elevated serum total cholesterol levels at a dose of 10 mg/kg in hamsters).
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DibenzOxepin derivatives: thromboxane A2 synthase inhibition and thromboxane A2 receptor antagonism combined in one molecule.
Journal of medicinal chemistry, 1993Co-Authors: Etsuo Ohshima, Hideyuki Sato, Hiroyuki Obase, Ichiro Miki, Akio Ishii, Michiyo Kawakage, Shiro Shirakura, Akira Karasawa, Kazuhiro KuboAbstract:A new series of 6,11-dihydrodibenz[b,e]Oxepin derivatives exerting both thromboxane synthase inhibitory (TXS-I) and thromboxane receptor antagonist (TXRA) activities is described. (-)-11-[(3-Pyridylmethyl)thio]-6,11-dihydrodibenz[b,e]Oxepin -2- carboxylic acid [(-)-3] and (E)-11-[2-(3-pyridyl)ethylidene]-6,11-dihydrodibenz[b,e]Oxepin+ ++-2- carboxylic acid methanesulfonate (11E) exhibited potent inhibitory effects on bovine platelet thromboxane synthase with IC50 values of 4.0 and 14 nM, respectively, and these derivatives also antagonized guinea pig platelet TXA2/PGH2 receptors with Ki values of 85 and 180 nM, respectively. Compound 11E exhibited the dual inhibitory activity in ex vivo experiments and demonstrated a significant protective effect in a rat acute renal failure model.
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Synthesis of a Dibenz[b, e]Oxepin-Bovine Serum Albumin Conjugate for Radioimmunoassay of KW-4679 ((Z)-11-[3-(Dimethylamino)propylidene]-6, 11-dihydrodibenz[b, e]Oxepin-2-acetic Acid Hydrochloride)
Chemical & pharmaceutical bulletin, 1992Co-Authors: Etsuo Ohshima, Hideyuki Sato, Hiroyuki Obase, Tatsuo Uchimura, Takashi Kuwabara, Satoshi KobayashiAbstract:(Z)-11-[3-(Dimethlamino)propylidene]-2-(methoxycarbonyl)methyl-6, 11-dihydrodibenz[b, e]Oxepin-9-acrylic acid (5) was prepared for application to the radiommunoassay of KW-4679 (1, (Z)-11-[3-(dimethylamino)propylidene]-6, 11-dihydrodibenz[b, e]Oxepin-2-acetic acid hydrochloride). The acrylic acid moiety in the 9-position of 5 was employed for coupling with an amino group of bovine serum albumin (BSA) to provide 17. Subsequently, the conjugate 17 was treated with aquenus NaOH to hydrolyze the terminal methoxycarbonyl group in the 2-position of the BSA conjugated 5. Antiserum raised against the antigenic BSA-conjugate 4 finally obtained was specific for 1.
Shiro Shirakura - One of the best experts on this subject based on the ideXlab platform.
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Inhibitors of Acyl-CoA:Cholesterol Acyltransferase. 1. Synthesis and Hypocholesterolemic Activity of Dibenz[b,e]Oxepin-11-carboxanilides
Journal of medicinal chemistry, 1994Co-Authors: Toshiaki Kumazawa, Hiroyuki Obase, Shiro Shirakura, Kazuhiro Kubo, Masashi Yanase, Hiroyuki Harakawa, Eiko Ohishi, Shoji Oda, Koji YamadaAbstract:A series of N-phenyl-6,11-dihydrodibenz[b,e]Oxepin-11-carboxamides and related derivatives were prepared on the basis of structures of the reported inhibitors of acyl-CoA:cholesterol acyltransferase (ACAT). These compounds were tested for their ability to inhibit ACAT (liver microsomes from cholesterol-fed rabbits) in vitro and to decrease serum total cholesterol in cholesterol-fed golden hamsters in vivo. The structure-activity relationships in vitro were as follows. Substitution at positions 2 and 6 in the anilide resulted in potent inhibitory activity, and the potency increased with increasing size of the substituents, with maximum potency being obtained with a 2,6-diisopropyl substitution. The position of the substituent on the dibenz[b,e]Oxepin ring system influenced the activity, and substitution at position 2 was critical for potent activity. The electronic effect of the substituent at position 2 does not influence activity, but bulkiness seems to be a significant factor. The lipophilicity of the compounds also plays an important role in determining ACAT inhibitory activity. Among the compounds tested, 2-bromo-N-(2,6-diisopropylphenyl)-6,11-dihydrodibenz-[b,e]++ +Oxepin-11- carboxamide (33, KF17828) showed significant in vitro activity (rabbit liver microsomes IC50 = 23 nM) and the most potent in vivo activity (complete reduction in elevated serum total cholesterol levels at a dose of 10 mg/kg in hamsters).
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DibenzOxepin derivatives: thromboxane A2 synthase inhibition and thromboxane A2 receptor antagonism combined in one molecule.
Journal of medicinal chemistry, 1993Co-Authors: Etsuo Ohshima, Hideyuki Sato, Hiroyuki Obase, Ichiro Miki, Akio Ishii, Michiyo Kawakage, Shiro Shirakura, Akira Karasawa, Kazuhiro KuboAbstract:A new series of 6,11-dihydrodibenz[b,e]Oxepin derivatives exerting both thromboxane synthase inhibitory (TXS-I) and thromboxane receptor antagonist (TXRA) activities is described. (-)-11-[(3-Pyridylmethyl)thio]-6,11-dihydrodibenz[b,e]Oxepin -2- carboxylic acid [(-)-3] and (E)-11-[2-(3-pyridyl)ethylidene]-6,11-dihydrodibenz[b,e]Oxepin+ ++-2- carboxylic acid methanesulfonate (11E) exhibited potent inhibitory effects on bovine platelet thromboxane synthase with IC50 values of 4.0 and 14 nM, respectively, and these derivatives also antagonized guinea pig platelet TXA2/PGH2 receptors with Ki values of 85 and 180 nM, respectively. Compound 11E exhibited the dual inhibitory activity in ex vivo experiments and demonstrated a significant protective effect in a rat acute renal failure model.
