ライフサイエンスコーパス: cyclopentenone

1 isoteucladiol (five steps and 21% yield from cyclopentenone).

2 teps from commercially available 4-hydroxy-2-cyclopentenone.

3 ar way starting with (S)-5-chloro-5-methyl-2-cyclopentenone.

4 nation by H(2)O to produce the indanone or 2-cyclopentenone.

5 the thermal cheletropic decarbonylation of 3-cyclopentenone.

6 an alpha-alkylidene and an alpha-silylidene cyclopentenone.

7 then oxidatively rearranged to generate the cyclopentenone.

8 ntrolled, and high-yielding synthesis from 2-cyclopentenone.

9 Dieckmann sequence furnishes the spirocyclic cyclopentenone.

10 ing a Johnson-Corey-Chaykovsky reaction on a cyclopentenone.

11 nexpectedly produces an allene oxide-derived cyclopentenone.

12 lkylidene cyclobutanones or beta-substituted cyclopentenones.

13 tramolecular HWE reaction to give nonracemic cyclopentenones.

14 ion that allows the synthesis of substituted cyclopentenones.

15 novel structural type from these spirocyclic cyclopentenones.

16 extended to the synthesis of tetralones and cyclopentenones.

17 the other via an electrophile effect of the cyclopentenones.

18 neutral method of synthesizing alpha-acyloxy cyclopentenones.

19 synthetic strategy for the construction of 2-cyclopentenones.

20 to classical Pauson-Khand-type syntheses of cyclopentenones.

21 cyclobutenamides instead rearrange to vinyl cyclopentenones.

22 e-alkyne cycloaddition affords the analogous cyclopentenones.

23 Cyclopentenone (+)-12 was prepared in 78% yield and 86%

24 ld) from D-glyceraldehyde acetonide, and the cyclopentenone (+)-14, prepared in one step (75-85% yiel

25 The cyclopentenone 15-deoxy-Delta(12,14)-prostaglandin J(2)

26 ted quiescent MCF-7 breast cancer cells with cyclopentenone (2-cyclopenten-1-one) blocked progression

27 selective [2+2] cycloaddition of 3-methyl-2-cyclopentenone, 2-cyclohexenone, and 2-methyl-2-cyclopen

28 ained derivative (trans,trans-2,5-dimethyl-3-cyclopentenone, 4) has been determined for the first tim

29 ves allows the preparation of polyoxygenated cyclopentenones (8) in a "one-pot" procedure.

30 ioxol-4-one ((4R, 5R)-4,5-O-isopropylidene-2-cyclopentenone) (8), which was achieved by modifying rep

31 syntheses of D- and l-4,5-O-isopropylidene-2-cyclopentenone (9 and 22), versatile intermediates for t

32 dehydration to afford stereoselectively the cyclopentenone alkylidene structural motif of the molecu

33 bstituted aryls, to some extent, favored the cyclopentenone alpha-regioisomer, while the EWG-substitu

34 Cyclopentenone also decreased the abundance of cyclin D1

35 short syntheses of the enantiomerically pure cyclopentenone and cyclohexene building blocks 5 and 6,

36 of (+/-)-teucladiol required five steps from cyclopentenone and proceeded in 28% overall yield; adapt

37 The stereochemistry of the cyclopentenone and the ratio of HWE to aldol products we

38 for the preparation of the 2,3-disubstituted cyclopentenones and cyclohexenones, which are key achira

39 oxides, highly reactive epoxides leading to cyclopentenones and other products.

40 Six- and seven-membered ring-fused cyclopentenones and piperidine- and tetrahydropyran-fuse

41 reaction for glucose, while the formation of cyclopentenones and small molecules was predominant for

42 , nonracemic alpha-acyloxy and alpha-hydroxy cyclopentenones and their corresponding redox derivative

43 containing unsymmetrical (cyclohexenone and cyclopentenone) and symmetrical (cyclohexene and cyclope

44 a Stetter cyclization to access the pendant cyclopentenone, and a highly chemoselective lactam reduc

45 o be precursors to alpha-hydroxy ketones and cyclopentenones, and as coupling partners in Suzuki-type

46 + 2]-cycloaddition of chalcones, conjugated cyclopentenones, and cyclohexenones with electron-rich a

47 We report a synthetic route to cyclopentenone-annulated [18]- and [24]dehydroannulenes

48 The corresponding monocyclic cyclopentenones are formed in good yields and excellent

49 ienone-butenolides, and spirocyclohexadenone-cyclopentenones are formed in yields up to 99 % and with

50 In particular, chiral cyclopentenones are important precursors in the asymmetr

51 ] ring system possessing an alpha-alkylidene cyclopentenone as a result of a selective reaction with

52 The reaction leads to the formation of cyclopentenones as single diastereoisomers that incorpor

53 e-pot elimination provides the corresponding cyclopentenones as well.

54 procedure for tandem reductive allylation of cyclopentenones, as well as the minimization of redox ma

55 novel 10Z isomer spontaneously formed a cis-cyclopentenone at room temperature in hexane.

56 Six- and seven-membered ring-fused cyclopentenones bearing a pendant alpha-hydrazineyl moie

57 es and piperidine- and tetrahydropyran-fused cyclopentenones bearing a pendant hydrazino functionalit

58 Highly functionalized cyclopentenones can be generated by a chemoselective cop

59 arrangement of oxiranylpropargylic esters to cyclopentenones catalyzed by PtCl(2) is proposed based o

60 eptenone (COMC-7), and 2-crotonyloxymethyl-2-cyclopentenone (COMC-5) to 2-glutathionylmethyl-2-cycloh

61 olenic acid to alpha-ketol, gamma-ketol, and cyclopentenone compounds that arise from spontaneous hyd

62 e method for the synthesis of trisubstituted cyclopentenones containing a 1,4-diketone moiety was dev

63 Cyclopentenones containing a 4-(methylsulfonyl)phenyl gr

64 Four cyclopentenone-containing ansamycin polyketides (mccrear

65 prostane rings are unstable and dehydrate to cyclopentenone-containing compounds possessing A-type an

66 dized EPA demonstrated the presence of novel cyclopentenone-containing molecules termed J3-isoprostan

67 4]dehydroannulenes are designed so that each cyclopentenone corner bears a dimethylacetal group on th

68 Replacing cyclopentenone corners with more electron-withdrawing cy

69 ly known to be JA-dependent, suggesting that cyclopentenones could fulfill some JA roles in vivo.

70 the efficient synthesis of trans-4,5-diamino cyclopentenones (DCP) using a high-pressure promoted Naz

71 15-deoxy-Delta(12,14)-PGJ(2), a cyclopentenone derivative of PGD(2), was recently report

72 ne-pot synthesis of ring-fused 5-hydrazino-2-cyclopentenone derivatives is achieved by a gold(I)-cata

73 synthesis of ring-fused, alpha-hydrazineyl-2-cyclopentenone derivatives is achieved by a gold(I)-cata

74 of fully substituted dienones that provides cyclopentenone derivatives with vicinal quaternary stere

75 s and Gdm D confirmed that the mccrearamycin cyclopentenone derives from benzilic acid rearrangement

76 Postfunctionalization transformations on the cyclopentenones (e.g., demethylation and saponification)

77 Thus, it is suggested that cyclopentenones feed back to inhibit continued nuclear a

78 [2 + 2 + 1] carbocyclization yields a novel cyclopentenone for elaboration to 1.

79 -bearing substrates) or unexpected 2-amino-2-cyclopentenones (for aminoenals) are described.

80 yne-dependent electronic regioselectivity of cyclopentenone formation in PKR with norbornene and ster

81 of the enynyl acetate dictates regioisomeric cyclopentenone formation.

82 otential unique biocatalyst in mccrearamycin cyclopentenone formation.

83 lopentenone, 2-cyclohexenone, and 2-methyl-2-cyclopentenone, forming their respective exo head-to-tai

84 allow rapid access to oxidatively transposed cyclopentenones from simple PKR products.

85 provided a facile access to various bicyclic cyclopentenones fused with either a carbocyclic or a het

86 stereocontrolled condensations led to a key cyclopentenone harboring a spirocyclic oxazoline.

87 A new approach to 2,3-disubstituted cyclopentenones has been developed.

88 A range of 2,3-disubstituted cyclopentenones has been generated, including short synt

89 gement reactions of allenylcyclopropanols to cyclopentenones have been achieved by means of Et2Zn/CuC

90 Indanones and 2-cyclopentenones have been successfully prepared in good

91 f asymmetry from the chiral auxiliary to the cyclopentenone in the allene ether version of the Nazaro

92 enantioselective and asymmetric syntheses of cyclopentenones, including chemical and enzymatic resolu

93 The overall results suggest that cyclopentenone interferes with the transcription initiat

94 e utility of D- and l-4,5-O-isopropylidene-2-cyclopentenone is demonstrated by their application for

95 chemical utility of the obtained enantiopure cyclopentenones is demonstrated.

96 e transformation of vinyl allene oxides into cyclopentenones is key to the biosynthesis of a number o

97 e preparation of nonracemic alpha-alkylidene cyclopentenones is necessary in order to obtain syntheti

98 intermolecular synthesis of polysubstituted cyclopentenones is reported.

99 on these observations, we questioned whether cyclopentenone-IsoP compounds are formed from the oxidat

100 Herein, we report the formation of cyclopentenone-IsoP molecules, termed A(3)/J(3)-IsoPs, f

101 increased generation of A(2)-isoprostane, a cyclopentenone isoprostane that blunts inflammation.

102 The cyclopentenone isoprostanes (A(2)/J(2)-IsoPs) are formed

103 Cyclopentenone isoprostanes (IsoPs), highly reactive str

104 and cyclooxygenase-2 were also inhibited by cyclopentenone IsoPs as was nitrite and prostaglandin pr

105 These findings suggest that cyclopentenone IsoPs may serve as negative feedback regu

106 Cyclopentenone IsoPs potently inhibited lipopolysacchari

107 2- and 15-J2-IsoPs, two groups of endogenous cyclopentenone IsoPs, on the inflammatory response in RA

108 ple starting materials, structurally complex cyclopentenones may be rapidly assembled.

109 Oxidative transpositions of bicyclic cyclopentenones mediated by selenium dioxide (SeO(2)) ar

110 s, such as the prostaglandin (PG) D2-derived cyclopentenone metabolite, 15d-PGJ2, produced by the cyc

111 Prostaglandin D(2) and its cyclopentenone metabolites [cyclopentenone prostaglandin

112 dition was developed for the assembly of its cyclopentenone moiety, and the challenging trans-diol mo

113 ly modifies ERalpha protein via its reactive cyclopentenone moiety, evidenced by incorporation of bio

114 ral structural element of our synthesis is a cyclopentenone motif that allows the assembly of the nat

115 between simple pyridines, Michael acceptors (cyclopentenone, N-methylmaleimide), and monoalkyl-3,3-di

116 We thus explored whether cyclopentenone neuroprostanes (A(4)/J(4)-neuroprostanes)

117 One class of compounds are cyclopentenone neuroprostanes (A(4)/J(4)-NPs), which are

118 ylidene cyclopentenone to the (Z)-silylidene cyclopentenone occurs upon purification of these product

119 We conclude that the jasmonate family cyclopentenone OPDA (most likely together with dinor OPD

120 eophiles to dienyl diketones produces either cyclopentenone or 2H-pyran products with high selectivit

121 yclobutenone to be more reactive than either cyclopentenone or cyclohexenone.

122 In this study we examined the role of the cyclopentenone PG 15-deoxy-Delta(12,14)-PGJ(2) (15d-PGJ(

123 ndin J(2) (15d-PGJ(2) ), collectively called cyclopentenone PGs (CyPGs).

124 ogether, these findings implicate a role for cyclopentenone PGs in CRC cell proliferation.

125 oxy-Delta(12,14)-PGJ2 (15d-PGJ2) and related cyclopentenone PGs inhibit caspase-1 activation by the N

126 for the anti-inflammatory properties of the cyclopentenone PGs through inhibition of caspase-1 and t

127 Na+-salicylate and cyclopentenone PGs, direct inhibitors of IKK beta, inter

128 We report that J-series cyclopentenone PGs, particularly PGJ2 and 15-deoxy-delta

129 le 3R,7S-JA as well as altered levels of its cyclopentenone precursors OPDA and dinor OPDA.

130 conversion of racemic allene to enantiopure cyclopentenone product in a dynamic kinetic asymmetric t

131 e-Rh(I) catalyst that provided alpha-acyloxy cyclopentenone product in up to 14:86 er.

132 ded to generate a single diastereomer of the cyclopentenone product obtained experimentally.

133 y chiral, very high enantiomeric excesses of cyclopentenone products are observed in the matched case

134 ituted diazomethane reagents, which provided cyclopentenone products in excellent yields and essentia

135 ly available alkynes can be used to generate cyclopentenone products via formation of the vinyl iodid

136 eoisomer of the 5-substituted 2-alkylidene-3-cyclopentenone products was obtained with Pt(0), but the

137 norbornene, mediated by Co(2)(CO)(8) to give cyclopentenone products, were examined in this study.

138 ensable in the efficient synthesis of the PK cyclopentenone products.

139 The former leads to increased levels of the cyclopentenone prostaglandin 15-deoxy- (12,14)-prostagla

140 The former leads to increased levels of the cyclopentenone prostaglandin 15-deoxy-Delta(12,14)-prost

141 Treatment with the PPARgamma ligand, the cyclopentenone prostaglandin 15-deoxy-Delta-prostaglandi

142 The cyclopentenone prostaglandin 15-deoxydelta-prostaglandin

143 4-Hydroxy-2-nonenal, 4-oxo-2-nonenal, and cyclopentenone prostaglandin A and J, which all contain

144 mechanisms of the protective effect of this cyclopentenone prostaglandin are--at least in part--PPAR

145 Cyclopentenone prostaglandin derivatives of arachidonic

146 notype, where cyclooxygenase (COX)-dependent cyclopentenone prostaglandin J2 (15d-PGJ2) plays a key r

147 This cyclopentenone prostaglandin triggered endoplasmic retic

148 oM, 4-hydroxyhexenal 38.9 microM) and by the cyclopentenone prostaglandin, 15-deoxy-delta(12,14)-pros

149 Thiol reactive cyclopentenone prostaglandin, 15-deoxy-Delta(12,14)-pros

150 eta-unsaturated carbonyl compounds, e.g. the cyclopentenone prostaglandin, 15-deoxy-Delta12,14-PGJ(2)

151 Previous studies have demonstrated that cyclopentenone prostaglandins (cyPG) inhibit human immun

152 Cyclopentenone prostaglandins (CyPG), such as 15-deoxy-D

153 Cyclopentenone prostaglandins (cyPGs) are reactive lipid

154 n datasets identified cyclooxygenase-derived cyclopentenone prostaglandins (CyPGs) as likely agents t

155 as dependent on the production of endogenous cyclopentenone prostaglandins (CyPGs), Delta-12 prostagl

156 din D(2) and its cyclopentenone metabolites [cyclopentenone prostaglandins (CyPGs)], Delta(12)prostag

157 f NF-kappa B activity, sodium salicylate and cyclopentenone prostaglandins (prostaglandin A(1) and 15

158 Cyclopentenone prostaglandins A2 and J2 are reactive com

159 hanistic link between UCH-L1 modification by cyclopentenone prostaglandins and the etiology of neurod

160 We examined the influence of cyclopentenone prostaglandins and their precursors on ac

161 NF-kappaB failed to translocate because the cyclopentenone prostaglandins attenuated degradation of

162 trol transcription of this gene and that the cyclopentenone prostaglandins can inhibit NF-kappaB acti

163 Here we show that modification of UCH-L1 by cyclopentenone prostaglandins causes unfolding and aggre

164 are highly functional cyclopentadienone and cyclopentenone prostaglandins chlorinated at the endocyc

165 We report that electrophilic cyclopentenone prostaglandins covalently modify and inhi

166 Cyclopentenone prostaglandins exhibit unique antineoplas

167 cation of NF-kappaB, and we confirm that the cyclopentenone prostaglandins inhibit NF-kappaB.

168 phenotype in cells exposed to electrophilic, cyclopentenone prostaglandins of the A and J series.

169 y, the effects of anti-inflammatory J series cyclopentenone prostaglandins on chemokine production by

170 reactive structural isomers of the bioactive cyclopentenone prostaglandins PGA2 and PGJ2, are formed

171 Cyclopentenone prostaglandins were potent inhibitors of

172 One of the most potent cyclopentenone prostaglandins, 15-deoxy-Delta(12,14)pros

173 Chemically reactive lipids, e.g. cyclopentenone prostaglandins, formed a covalent adduct

174 cal effects of 15-d-PGJ(2), and likely other cyclopentenone prostaglandins, in a glutathione-dependen

175 J(2)), a terminal metabolite of the J-series cyclopentenone prostaglandins, influences a variety of c

176 the existence of a novel pathway mediated by cyclopentenone prostaglandins, which may represent part

177 protein, and aggregates upon conjugation by cyclopentenone prostaglandins.

178 nd similar in structure to anti-inflammatory cyclopentenone prostaglandins.

179 or the first time, the in vivo production of cyclopentenone prostanoids.

180 These results explain the origin of the cyclopentenone, provide insights into the mechanisms of

181 oxiranylpropargylic ester 13, a racemate of cyclopentenone (R*,S*)-16 was obtained.

182 l or CuCN.2LiCl to afford 5-alkyl or 4-alkyl cyclopentenone regioisomers: the former conditions affor

183 ituted alkynes are known to guide alpha/beta-cyclopentenone regioselectivity in the cobalt-mediated P

184 2-cycloheptenone, and 2-glutathionylmethyl-2-cyclopentenone, respectively.

185 sence of water furnishes di- and trioxidized cyclopentenones, respectively.

186 resulting in the alpha- or beta-substituted cyclopentenones, respectively.

187 The cyclopentenone response element did not correspond to th

188 Deletion analysis indicated that the cyclopentenone response element was located in the cycli

189 eactive alpha,beta-unsaturated ketone in the cyclopentenone ring of 15d-PGJ(2) covalently modifies ke

190 lpha,beta-unsaturated carbonyl center in the cyclopentenone ring of prostaglandins, resulting in a co

191 /J(4)-neuroprostanes contain highly reactive cyclopentenone ring structures, it would be predicted th

192 opentenone bearing at second position of the cyclopentenone ring the thiophene unit displays high the

193 of the endocyclic carbon double bond in the cyclopentenone ring was key, generating a new stereogeni

194 cks the electrophilic carbon of the 15d-PGJ2 cyclopentenone ring, activated PPARgamma but did not kil

195 amma and are dependent on an intact reactive cyclopentenone ring.

196 voring the beta-position in the newly formed cyclopentenone ring.

197 adjacent quaternary centers arrayed around a cyclopentenone ring.

198 favor the beta-position in the newly formed cyclopentenone ring.

199 acetate led to efficient construction of the cyclopentenone scaffold.

200 Cyclopentenone selectively inhibited the activity of the

201 eta-isopropoxy group in a 2,3-diisopropoxy-2-cyclopentenone setting; and (c) conventional conversion

202 e rapid preparation of highly functionalized cyclopentenones, several of which are new chemical entit

203 for the construction of novel bicyclic fused cyclopentenones starting from Morita-Baylis-Hillman (MBH

204 se it cannot be reproduced by other PGs with cyclopentenone structure.

205 ng for the dynamic kinetic resolution of the cyclopentenone substrates.

206 11,14-eicosatetraenoic acid from which arise cyclopentenones such as the prostanoid-related clavulone

207 is complementary to conventional methods for cyclopentenone synthesis.

208 es have a structural determinant (endocyclic cyclopentenone) that confers the ability to impair the c

209 work, the formation of synthetically useful cyclopentenones through a formal C-H functionalization s

210 tion is a powerful tool for the synthesis of cyclopentenones through the efficient [2 + 2 + 1] cycloa

211 dergo an isomerization of the (Z)-alkylidene cyclopentenone to the (E)-alkylidene cyclopentenone when

212 ies, but isomerization of the (E)-silylidene cyclopentenone to the (Z)-silylidene cyclopentenone occu

213 by cycloaddition of (R)-5-chloro-5-methyl-2-cyclopentenone to the 1,3-dipolar intermediate from 1-ac

214 Growth arrest of the cyclopentenone-treated cells in G1 was associated with c

215 The cyclopentenone unit is a very powerful synthon for the s

216 asymmetric functionalization of the existing cyclopentenone unit, and functionalization of chiral bui

217 mation from an allene to the 5-position of a cyclopentenone using a cyclocarbonylation reaction.

218 intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis.

219 lylic silane 3a was prepared from 2-methyl-2-cyclopentenone via a copper-catalyzed 1,4-addition follo

220 ed 2,3,4-triarylcyclopent-2-en-1-ones from 2-cyclopentenone via sequential functionalization of a nov

221 The generation of dibrominated cyclopentenones via an interrupted Nazarov cyclization i

222 former conditions afford 5-alkyl substituted cyclopentenones via beta-carbon elimination, whereas the

223 c or easily deprotonated exclusively produce cyclopentenones via Nazarov cyclization, whereas the neu

224 of the diastereomers of the alpha-alkylidene cyclopentenones was encountered, leading to eventual dec

225 As a result, a number of chiral cyclopentenones were easily synthesized in good to excel

226 Bicyclic cyclopentenones were obtained in up to 75% enantiomeric

227 Functionalized cyclopentenones were synthesized by the diazomethane rin

228 ylidene cyclopentenone to the (E)-alkylidene cyclopentenone when exposed to acidic conditions.

229 dergo cyclization to yield 3-chloro-5-aryl-2-cyclopentenones when treated with AlCl(3).

230 Reduction of (+/-)-5-chloro-5-methyl-2-cyclopentenone with BH(3).THF and catalytic (R)-2-methyl

231 alkynes to form the carbon framework of the cyclopentenone with Cr(CO)(6) serving as an easy to hand

232 i-catalyzed pentannulation of functionalized cyclopentenone with methylenecyclopropane and subsequent

233 ment of sulfonium leads after cyclization to cyclopentenones with a C4-quaternary stereocenter.

234 ess to synthetically versatile alpha'-chiral cyclopentenones with excellent enantiomeric excesses fro

235 4-aryloxy-, 4-amino-, or 4-thio-substituted cyclopentenones with high enantioselectivity by palladiu

236 aromatic side chains afford alpha-alkylidene cyclopentenones with the opposite diastereoselectivity c

237 ereospecific Nazarov cyclization that led to cyclopentenones with vicinal all-carbon-atom quaternary