ライフサイエンスコーパス: oxindole

1 in formation of an alpha,alpha-disubstituted oxindole.

2 ucial and highly congested 3,3-disubstituted oxindole.

3 dation undergoes further rearrangement to an oxindole.

4 eady access to N-carbamoyl-3-monosubstituted oxindoles.

5 aternary carbon in alpha,alpha-disubstituted oxindoles.

6 hods for the synthesis of 3,3'-disubstituted oxindoles.

7 d carbonate derivatives of the antirheumatic oxindole 1 were prepared and screened as potential prodr

8 The series of 3-monofunctionalized 2-oxindoles 2 were conveniently synthesized from reactions

9 benzenesulfonyl chloride 2, the N-protected oxindole 3, and protected dibromide 4.

10 In this article, we have demonstrated that 2-oxindole-3-acetic acid (oxIAA) is a major primary IAA ca

11 oxidation of IAA to its primary catabolite 2-oxindole-3-acetic acid (oxIAA) remains uncharacterized.

12 d in Zea seedlings: Indole-3-acetic acid --> Oxindole-3-acetic acid --> 7-Hydroxyoxindole-3-acetic ac

13 t is present at levels comparable to that of oxindole-3-acetic acid and indole-3-acetic acid (62 pico

14 Indole-3-acetic acid is oxidized to oxindole-3-acetic acid by Zea mays tissue extracts.

15 enzymic oxidation of indole-3-acetic acid to oxindole-3-acetic acid in higher plants.

16 ific showing no glucose ester formation with oxindole-3-acetic acid or 7-hydroxy-oxindole-3-acetic ac

17 Radiolabeled oxindole-3-acetic acid was metabolized by roots, shoots,

18 ion with oxindole-3-acetic acid or 7-hydroxy-oxindole-3-acetic acid, and low activity with phenylprop

19 the kernel, more than 10 times the amount of oxindole-3-acetic acid.

20 2-oxindole-3-alkylcarboxylates, this direct alkynylations

21 owth factor receptor 1 kinase inhibitor) and oxindole (a vascular endothelial growth factor receptor

22 It was found that 5-Br-3-oxindole, a precursor of the product 5-Br-3-oxindolenine

23 rm 3,3-disubstituted pyrrolidines, including oxindole alkaloids.

24 between the E and Z isomers of the starting oxindoles allowed a site-specific diastereoselective and

25 ooxygenated products were found to be 5-Br-2-oxindole and 5-Br-3-oxindolenine.

26 s forges two bonds en route to spirocyclized oxindole and indolenine products.

27 are broad in scope with respect to both the oxindole and nitroolefin substrates and provide the desi

28 tolerate a range of substitution on both the oxindole and the aryl/vinyl coupling partners.

29 ion that simultaneously constructs the spiro-oxindole and vinyl isonitrile moieties.

30 loped by employing 3-(2-oxo-2-arylethylidene)oxindoles and 1,4-benzoxazinone as starting materials.

31 atile route to enantiopure 3,3-disubstituted oxindoles and 3a-substituted pyrrolidinoindolines is des

32 By the application of 3-olefinic oxindoles and benzofuranone, biologically relevant spiro

33 ectivity for a variety of unprotected 3-aryl oxindoles and benzylic methyl carbonates using chiral bi

34 construction of a C-C bond between 3-ylidene oxindoles and electron-rich arenes has been successfully

35 ect construction of a range of spirocyclized oxindoles and indolenines in good to excellent yields.

36 report the palladium-catalyzed reactions of oxindoles and indoles, both functioning as bis-nucleophi

37 Michael-aldol reaction between 3-substituted oxindoles and methyleneindolinones that affords complex

38 Starting from simple alkylidene oxindoles and nitroketones, a highly stereoselective met

39 s been utilized in solid-phase approaches to oxindoles and tetrahydroquinolones.

40 This method provides alternative access to oxindoles and their biologically active derivatives.

41 Oxindoles and their indoline derivatives are common stru

42 d indazole, benzimidazole, pyrazole, indole, oxindole, and azaindole halides under mild conditions in

43 ore was accomplished in 13 steps using a new oxindole annulation and late-stage enamine oxidation.

44 ric syntheses of diversely 3,3-disubstituted oxindoles are currently developed, this isomerization pr

45 icle describes our work regarding the use of oxindoles as carbon-based nucleophiles in a Pd-catalyzed

46 d asymmetric benzylic alkylation with 3-aryl oxindoles as prochiral nucleophiles.

47 ed catalyst system chemoselectively arylated oxindole at the 3 position, while arylation occurred exc

48 Phe(B27)RLF (21%), D-Trp(B27) (26%), and the oxindole(B27)RLF (41%).

49 Walter Reed chemical database, we identified oxindole-based compounds as effective inhibitors of Pfmr

50 Two closely related classes of oxindole-based compounds, 1H-indole-2,3-dione 3-phenylhy

51 proparyloxy-substituted indoles to generate oxindoles bearing allyl- or allenyl-substituted quaterna

52 The gamma-functionalization of oxindoles bearing nonsymmetric 3-alkylidene groups via v

53 The novel fluoro-oxindoles BMS-204352 and racemic compound 1 are potent,

54 rates for a palladium-catalyzed synthesis of oxindoles by amide alpha-arylation.

55 ion-metal-free method to construct N-hydroxy oxindoles by an aza-Nazarov-type reaction involving azao

56 atalyst system, the corresponding 3-arylated oxindoles can be obtained in good to excellent yields (<

57 al benzylic ether serves as an auxiliary for oxindole carboxylation (dr 5.2:1.0) that sets C10 config

58 tive alpha-arylation and alpha-vinylation of oxindoles catalyzed by Pd and a biarylmonophosphine liga

59 bitors led to novel, chemically stable spiro-oxindole compounds bearing a spiro[3H-indole-3,2'-pyrrol

60 s, whereas the moieties that extend from the oxindole contact residues in the hinge region between th

61 atalyst derived from Pd(OAc)(2) to construct oxindoles containing a diaryl-substituted all-carbon qua

62 nhibitors was identified that is based on an oxindole core (indolinones).

63 tiated the adenine mimetic properties of its oxindole core.

64 can be used to access biologically relevant oxindole cores.

65 ry carbon center are derived from alkylidene oxindole, coumarin, and malonate substrates with high st

66 rated challenging (i.e., alpha-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azl

67 a model of precursors for Hartwig asymmetric oxindole cyclizations.

68 Oxidation of the spirocyclic oxindole derivative, isamic acid 1, led to decarboxylati

69 bstrates led to the formation of spirocyclic oxindole derivatives in good yields with complete regios

70 We have investigated several oxindole derivatives in the pursuit of a 5-HT7 receptor

71 iourea-catalyzed asymmetric 1,4-additions of oxindole derivatives to nitroolefins as a key step.

72 were used under mild conditions to construct oxindole derivatives with high enantiopurity and structu

73 ally relevant carbazoles, delta-lactams, and oxindole derivatives).

74 cient direct alkynylations of 3-alkyl/aryl 2-oxindoles employing ethynyl-1,2-benziodoxol-3(1H)-one (E

75 The route to oxindoles employs the first Pummerer cyclizations on sol

76 such as an intriguing propellane hexacyclic oxindole encountered in the communesin F sequence, are d

77 alkylation of enantiopure ditriflate 10 with oxindole enolates is the central step.

78 ridged indole 35, and rearrangement of 35 to oxindole ent-6.

79 onalities and the formation of 3-fluorinated oxindoles exhibiting an array of four adjacent centers o

80 igh-throughput crystallography identified an oxindole fragment bound to the S1 pocket of the protein

81 thod for the synthesis of 3-(chloromethylene)oxindoles from alkyne-tethered carbamoyl chlorides using

82 ulation of sulfonylphthalide with 3-olefinic oxindole has been performed.

83 The synthesis of dihydrobenzofuran-appended oxindoles has been accomplished taking advantage of an u

84 w anticancer therapeutic strategy, and spiro-oxindoles have been designed as a class of potent and ef

85 linear and cross-conjugated trienamines with oxindoles have been studied with density functional theo

86 In particular, 3,3'-disubstituted oxindoles have one or more asymmetric quaternary carbon

87 The reaction affords a variety of 2-oxindoles having quaternary center at the pseudobenzylic

88 affold resulted in a potent arylsulfoanilide-oxindole hybrid, 27.

89 The cocrystal structure of the related oxindole hydrazide c-MET inhibitor 10 with a nonphosphor

90 An oxindole hydrazide hit 6 was identified during a c-MET H

91 The chemically labile oxindole hydrazide scaffold was replaced with a chemical

92 Treatment with the oxindole/imidazole derivative C16 rescued oHSV-1 replica

93 Reactivity with 5-Br-3-oxindole in the absence of H2O2 also yielded 5,5'-Br2-in

94 nacol rearrangement for the formation of the oxindole in the final step.

95 aternary stereocenter or trifluoromethylated oxindoles in a regioselective manner.

96 access to novel spiro-dihydronaphthoquinone-oxindoles in excellent yields with complete selectivity

97 complex by azoles afforded 3,3-disubstituted oxindoles in good yields with excellent enantioselectivi

98 ide rapid access to a variety of spirocyclic oxindoles in one operation.

99 able steric bulk, can be introduced at C3 of oxindoles in this way (Table 4).

100 own to provide direct access to an important oxindole intermediate, could be applied to the total syn

101 The conversion of the beta-nitro oxindole into the corresponding beta-amino derivative di

102 Access to N-unsubstituted oxindoles is demonstrated by DPA cleavage with Et(2)NH.

103 ichael addition of nitroalkanes to 3-ylidene oxindoles is described, mediated by thiourea-based bifun

104 o quaternary C-acetylated and C-carboxylated oxindoles is observed, even for substrates containing br

105 ive cyclization of an N-Boc aniline onto the oxindole moiety to form a pentacyclic framework containi

106 The oxindole occupies the site in which the adenine of adeno

107 s wherein the first nucleophilic unit on the oxindole or indole reacts with an allenyl-palladium spec

108 ith the second nucleophilic component of the oxindole or indole.

109 the resulting palladium enolate to form the oxindole product.

110 xazoline catalysts were employed to generate oxindole products with 100% conversion and up to 92% ee.

111 olyheterocycles are skillfully embraced with oxindole, pyrrole, and coumarin scaffolds, which are wel

112 An initial subdeck screen revealed that the oxindole-pyrrolo[2,1- f][1,2,4]triazine lead 2a displaye

113 ylides of 1,3-dicarbonyls and 3-alkylidene-2-oxindoles results in 3H-spiro[furan-2,3'-indolin]-2'-one

114 Heck cyclization for the installation of the oxindole ring system as well as a directed hydrosilylati

115 it has been developed for the synthesis of 2-oxindoles sharing vicinal all-carbon quaternary stereoce

116 xperiments using enantioenriched 3-hydroxy-2-oxindole show that the reaction proceeds through in situ

117 cycloadditions with isatins 2a-2f to form 2-oxindole spirolactones 3a-3l.

118 Oxindoles substituted at N-1 by electron-withdrawing gro

119 C-H functionalization event involving a keto oxindole substrate to introduce the tetrahydrofuran ring

120 The synthesis of 3,3-difluoro-2-oxindoles through a robust and efficient palladium-catal

121 the preparation of functionalized 3-alkenyl-oxindoles through a Suzuki-Miyaura reaction.

122 Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or rev

123 les in a Pd-catalyzed asymmetric addition of oxindoles to allenes (Pd-catalyzed hydrocarbonation of a

124 d a wide variety of 3-alkynyl-3-alkyl/aryl 2-oxindole under transition-metal free condition.

125 owed that some of our first-generation spiro-oxindoles undergo a reversible ring-opening-cyclization

126 selective azidations of beta-keto esters and oxindoles using a readily available N3-transfer reagent

127 or the union of amides, imides, ketones, and oxindoles using soluble copper(II) or iron(III) salts as

128 ure for the synthesis of 3,3-disubstituted 2-oxindoles via cross-dehydrogenative coupling (CDC) is re

129 he cascade transformation of 3-(2-azidoethyl)oxindoles via Staudinger/aza-Wittig/Mannich reactions.

130 Regioselective N-carbamoylation of oxindoles was achieved through the use of imidazole carb

131 A series of 3-substituted 3-amino-2-oxindoles was obtained with excellent results (up to 99%

132 biologically relevant spiro[pyrrolidine-3,3'-oxindoles] was developed on the basis of the cascade tra

133 to a stereogenic carbon and an N-coordinated oxindole were synthesized by the reaction of alkenyl ary

134 zine]- and 3-spiro[3-azabicyclo[3.1.0]hexane]oxindoles were prepared in moderate to high yields via o

135 Oxadiazole substituted oxindoles were subsequently converted to pyrroloindoline

136 trated in the synthesis of 3,3-disubstituted oxindoles, which are prevalent motifs seen in numerous b

137 Replacement of the C4 oxindole with 2-methyl-5- N-methoxybenzamide aniline 9 g

138 for the allylation reactions of 3-hydroxy-2-oxindoles with allyltrimethylsilane has been developed.

139 the cross-coupling reactions of unprotected oxindoles with aryl halides, Pd- and Cu-based catalyst s

140 um-catalyzed monoselective C3 arylation of 2-oxindoles with aryl tosylates is described.

141 rnish synthetically viable enantioenriched 2-oxindoles with C-3 quaternary stereocenters.

142 allenols to efficiently afford 3-halodienyl-oxindoles with good yield and total selectivity.

143 rein we disclose a novel aminooxygenation of oxindoles with nitrosobenzene catalyzed by a newly desig

144 A cascade reaction of 3-ylidene oxindoles with phenols and beta-naphthol resulted in 2,3

145 thesized a series of second-generation spiro-oxindoles with symmetrical pyrrolidine C2 substitution.

146 construct a C-O bond at the C(3) position of oxindoles with the creation of an oxygen-containing tetr

147 reoselective synthesis of spiro(cyclopentene)oxindoles with trisubstituted cyclopentene units.

148 ilic ring opening of spiro[cyclopropane-1,3'-oxindoles] with the azide ion.

149 A series of new spiro[pyrrolidine-3,3'-oxindoles] with various (het)aryl substituents at the C2