ライフサイエンスコーパス: cyclopentenone

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

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

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

4 the thermal cheletropic decarbonylation of 3-cyclopentenone.

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

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

7 then oxidatively rearranged to generate the cyclopentenone.

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

9 nexpectedly produces an allene oxide-derived cyclopentenone.

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

11 neutral method of synthesizing alpha-acyloxy cyclopentenones.

12 novel structural type from these spirocyclic cyclopentenones.

13 extended to the synthesis of tetralones and cyclopentenones.

14 the other via an electrophile effect of the cyclopentenones.

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

16 cyclobutenamides instead rearrange to vinyl cyclopentenones.

17 e-alkyne cycloaddition affords the analogous cyclopentenones.

18 lkylidene cyclobutanones or beta-substituted cyclopentenones.

19 tramolecular HWE reaction to give nonracemic cyclopentenones.

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

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

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

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

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

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

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

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

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

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

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

31 Cyclopentenone also decreased the abundance of cyclin D1

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

47 Highly functionalized cyclopentenones can be generated by a chemoselective cop

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

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

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

51 Cyclopentenones containing a 4-(methylsulfonyl)phenyl gr

52 Four cyclopentenone-containing ansamycin polyketides (mccrear

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

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

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

56 15-deoxy-Delta(12,14)-PGJ(2), a cyclopentenone derivative of PGD(2), was recently report

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

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

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

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

61 [2 + 2 + 1] carbocyclization yields a novel cyclopentenone for elaboration to 1.

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

63 otential unique biocatalyst in mccrearamycin cyclopentenone formation.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

81 Cyclopentenone isoprostanes (IsoPs), highly reactive str

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

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

84 Cyclopentenone IsoPs potently inhibited lipopolysacchari

85 2- and 15-J2-IsoPs, two groups of endogenous cyclopentenone IsoPs, on the inflammatory response in RA

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

111 The cyclopentenone prostaglandin 15-deoxydelta-prostaglandin

112 4-Hydroxy-2-nonenal, 4-oxo-2-nonenal, and cyclopentenone prostaglandin A and J, which all contain

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

114 Cyclopentenone prostaglandin derivatives of arachidonic

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

116 This cyclopentenone prostaglandin triggered endoplasmic retic

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

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

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

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

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

122 Cyclopentenone prostaglandins (cyPGs) are reactive lipid

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

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

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

126 Cyclopentenone prostaglandins A2 and J2 are reactive com

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

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

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

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

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

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

133 We report that electrophilic cyclopentenone prostaglandins covalently modify and inhi

134 Cyclopentenone prostaglandins exhibit unique antineoplas

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

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

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

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

139 Cyclopentenone prostaglandins were potent inhibitors of

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

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

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

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

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

145 protein, and aggregates upon conjugation by cyclopentenone prostaglandins.

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

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

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

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

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

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

152 2-cycloheptenone, and 2-glutathionylmethyl-2-cyclopentenone, respectively.

153 The cyclopentenone response element did not correspond to th

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

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

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

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

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

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

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

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

162 adjacent quaternary centers arrayed around a cyclopentenone ring.

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

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

165 Cyclopentenone selectively inhibited the activity of the

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

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

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

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

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

171 11,14-eicosatetraenoic acid from which arise cyclopentenones such as the prostanoid-related clavulone

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

187 Bicyclic cyclopentenones were obtained in up to 75% enantiomeric

188 Functionalized cyclopentenones were synthesized by the diazomethane rin

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

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

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

192 4-aryloxy-, 4-amino-, or 4-thio-substituted cyclopentenones with high enantioselectivity by palladiu

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

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