ライフサイエンスコーパス: carbinol

1 n (FLIP) were all down-regulated by indole-3-carbinol.

2 n demonstrated in the case of methyl mesityl carbinol.

3 composed by reaction with the medium to give carbinol.

4 ield, and in the presence of the unprotected carbinol.

5 tiated rearrangement of protected thiazolium carbinols.

6 nyl-ene reaction) to functionalized tertiary carbinols.

7 mall number of methods can generate tertiary carbinols.

8 chiral diaryl carbinols and a few arylalkyl carbinols.

9 chirality transfer from the optically active carbinols.

10 use in the petrocortyne family of dialkynyl carbinols.

11 .995), ethyl isovalerate (-0.994) and benzyl carbinol (0.993) are the key variables that most contrib

12 ved through derivatization with deuterated 3-carbinol-1-methyl-d3-pyridinium iodide.

13 with 2-bromo-1-methylpyridinium iodide and 3-carbinol-1-methylpyridinium iodide, forming 3-acyloxymet

14 e-induced desilylation-cyclization to afford carbinol 12.

15 ,7-disubstituted fluoren-9-one to afford the carbinol 16.

16 re for the asymmetric epoxidation of divinyl carbinol (3) was described, and the product was used in

17 bly more advantageous for the acquisition of carbinol 37e than in the absence of the additive (exo/en

18 6 has the S,S and (-)-(methylenecyclopropyl)carbinol (4) the R configuration.

19 scorbigen (13.0 mumol/100 g FW) and indole-3-carbinol (4.52 mumol/100g FW) with their higher concentr

20 periments show that the reaction of indole-3-carbinol, a breakdown product of indol-3-ylmethylglucosi

21 Based on the structure of indole-3-carbinol, a chemopreventive phytochemical, we developed

22 IM) is a major digestive product of indole-3-carbinol, a potential anticancer component of cruciferou

23 her supporting the possibility that indole-3-carbinol acts as an auxin antagonist.

24 of otherwise unknown stereogenic, secondary carbinol (alcohol) centers (R1R2CHOH (or the analogous a

25 (TBAF) yielded polyfunctionalized (2E,4E)-4-carbinol alkadienoate-a valuable building block-in highl

26 idly added to silylallenes, leading to gamma-carbinol allenoates at low temperatures.

27 rotocol used involves the reaction of cyclic carbinol amides with triflic anhydride.

28 logue was oxidized to the syn spiromethylene carbinol analogue of the major spirosulfonamide product.

29 dipyrromethane and a 9-bromodipyrromethane-1-carbinol and (ii) intramolecular cyclization of the 1-br

30 ity including the reactive cyclopropylmethyl carbinol and alpha,beta-unsaturated ketone.

31 tency with the absolute configuration of the carbinol and amine moieties, whose observed DeltadeltaL(

32 d that oviposition was increased by indole-3-carbinol and decreased by indole-3-acetonitrile (IAN).

33 group are nonessential since both pyridine-3-carbinol and pyridine-4-carboxylate support the base exc

34 A direct interaction between indole-3-carbinol and the auxin perception machinery was suggeste

35 positioning of the substituents on both the carbinol and the cyclopropane determine both chemo- and

36 Benzofuranyl carbinols and 1,3-dicarbonyls in the presence of a catal

37 (2), with aldehydes to produce chiral diaryl carbinols and a few arylalkyl carbinols.

38 ocess is tolerant of a variety of thiazolium carbinols and nitroalkene substrates and can be rendered

39 Compounds containing acid, ester, amide, carbinol, and aldehyde groups at the 3-position of the q

40 rolide bearing an esterified trichloromethyl carbinol, and may be produced by a cyanobacterium that a

41 ercetin, flavone, chlorogenic acid, indole-3-carbinol, and rutin) and three insecticides (diazinon, c

42 monoacyl dipyrromethane to the corresponding carbinol, and self-condensation of the carbinol to form

43 es and of alpha-alkoxyallenyl vinyl tertiary carbinols are covered (Section 3).

44 These tertiary carbinols are formed in high diastereoselectivities, wit

45 The 8'-methyl carbinols are the only metabolites formed by CYP1A2, and

46 ides trisubstituted alpha-hydroxycyclopropyl carbinols as single diastereomers in good to excellent y

47 wn products (indole-3-acetonitrile, indole-3-carbinol, ascorbigen and 3,3'-diindolylmethane released

48 the absolute configuration of the lipid tail carbinols at pH 4.0 and 8.0.

49 group at the 5-position, a dipyrromethane-1-carbinol bearing an acetal group at the 5-position or ca

50 ecreasing the rotation rate of the quinoline-carbinol bond, the relatively bulky CF(3) group enables

51 ts for the kinetic resolutions of aryl alkyl carbinols by benzoylation (16, 21, 22) or iso-butyroylat

52 ation) is superseded by a pathway leading to carbinol C-alkylation under the conditions of rhodium-ca

53 ary alcohol reactant releases the product of carbinol C-alkylation with regeneration of the ketone.

54 ng studies, we determined that (i) it is the carbinol C-H and adjacent O-H hydrogen atoms that are tr

55 t the diene C4-position, resulting in direct carbinol C-H prenylation and geranylation, respectively.

56 ary alcohol reactant releases the product of carbinol C-H vinylation and regenerates ketone and zero-

57 Versatile trichloromethyl carbinols can be prepared in one pot from primary alcoho

58 uents at the carbons adjacent to the allylic carbinol carbon (i.e., C-2 or C-6 in cyclohexenone-deriv

59 ations involves hydride abstraction from the carbinol carbon of the alcohol substrate.

60 he unpaired electron is localized on C1 (the carbinol carbon) of the substrate.

61 methylmalate, involving the migration of the carbinol carbon.

62 experimental effects of substituents on the carbinol carbon.

63 stereochemistry is controlled from a single carbinol center installed through catalytic enantioselec

64 The configuration at the new carbinol center was deduced by proton NMR analysis of (R

65 The dramatic effect of the carbinol configuration on cytotoxicity was confirmed wit

66 id, diastereoselective synthesis of tertiary carbinol containing fragments with relevance to polyketi

67 ing enantioselective diboration of a divinyl carbinol derivative and high-yielding late-stage cross-m

68 r bromonium ion-induced rearrangement of the carbinol derived by addition of 2-lithio-4,5-dihydrofura

69 Vinyl carbinols derived from 2-methyl-2-phenylpropanal react w

70 romethane and a 9-protected dipyrromethane-1-carbinol (derived from a 9-protected 1-acyldipyrromethan

71 An alternative approach to the alpha-carbinol diastereomer proceeds by initial alpha-oxygenat

72 A bromodipyrromethane carbinol (Eastern half) was prepared by sequential acyla

73 Allenyl carbinol ester 3 isomerizes to an E,Z mixture of the cor

74 Although the carbinol esters yield stereo- and regiochemically hetero

75 tives (carboxylate esters, carboxamides, and carbinol esters) were investigated as substrates for rin

76 Carbinol formation is further characterized by high intr

77 Indole-3-carbinol, found in Brassica species vegetables (such as

78 on is induced by herbivory, such as indole-3-carbinol, function not only to repel herbivores, but als

79 The glucosinolate breakdown product indole-3-carbinol functions in cruciferous vegetables as a protec

80 oxidation of the resultant diastereoisomeric carbinols, gave the acetylenic ketone 24.

81 ns that focused on modifications to the aryl carbinol group of this series.

82 ons of steroids in the presence of secondary carbinol groups and carbon-carbon double bonds, as in en

83 Among them, sulforaphane and indole-3-carbinol have attracted a lot of attention, since their

84 posed reaction pathway, silylated thiazolium carbinols have been identified to provide good yields of

85 eaction is found to be general even on furyl carbinols; however, it generates the rearranged polysubs

86 Indole-3-carbinol (I3C) and 3,3'-diindolylmethane (DIM) are two b

87 chemical and biological interest in indole-3-carbinol (I3C) and its metabolites has resulted in the d

88 -231 human breast cancer cells with indole-3-carbinol (I3C) directly inhibited the extracellular elas

89 The indole-3-carbinol (I3C) metabolite 3,3'-diindolylmethane (DIM) is

90 Indole-3-carbinol (I3C), a component of Brassica vegetables, is u

91 Indole-3-carbinol (I3C), a compound naturally occurring in Brassi

92 ted the chemopreventive efficacy of indole-3-carbinol (I3C), a constituent of Brassica vegetables, an

93 Indole-3-carbinol (I3C), a dietary compound found in cruciferous

94 We investigated the efficacy of indole-3-carbinol (I3C), a dietary supplement, and AHR precursor

95 The effect of indole-3-carbinol (I3C), a major indolic metabolite in cruciferou

96 Dietary indole-3-carbinol (I3C), a natural compound present in vegetables

97 Indole-3-carbinol (I3C), a naturally occurring component of Brass

98 Indole-3-carbinol (I3C), a naturally occurring component of Brass

99 hed the cellular mechanism by which indole-3-carbinol (I3C), a promising anticancer phytochemical fro

100 ypothesized that the phytochemical, indole-3-carbinol (I3C), and some of its acid-condensation deriva

101 er the antiestrogenic phytochemical indole-3-carbinol (I3C), found in cruciferous vegetables, adminis

102 The phytochemical indole-3-carbinol (I3C), found in cruciferous vegetables, and its

103 The naturally occurring chemical indole-3-carbinol (I3C), found in vegetables of the Brassica genu

104 ral classes of compounds, including Indole-3-carbinol (I3C), may have chemopreventive activity agains

105 ovides phytochemicals, particularly indole-3-carbinol (I3C), which may be responsible for the prevent

106 The Tg is driven by the indole-3-carbinol (I3C)-inducible rat cytochrome P450 1A1 promote

107 treatment with the AHR pro-agonist indole-3-carbinol (I3C).

108 the ability of dietary AhR ligands (indole-3-carbinol [I3C] and 3,3'-diindolylmethane [DIM]) and an e

109 s determination of sulforaphane and indole-3-carbinol in broccoli using UPLC-HRMS/MS is described.

110 U-A9 was 100 times more potent than indole-3-carbinol in suppressing the viability of Hep3B, Huh7, an

111 onyl substrates to provide the corresponding carbinols in yields up to 99%.

112 t inhibit carcinogenesis, including indole-3-carbinol, indole-3-carboxaldehyde, ferulic acid, vanilli

113 ndole-containing chemicals, such as indole-3-carbinol, indolo[3, 2-b]carbazole, and UV photoproducts

114 administration of low-dose dietary indole-3-carbinol induces moderate hypertension.

115 Overall, our results indicated that indole-3-carbinol inhibits NF-kappaB and NF-kappaB-regulated gene

116 is responsible for the observed formation of carbinols instead of the desired haloketones.

117 Alternative protocols for carbinol inversion at C(11), one early and one late in t

118 rporation of oxygen from the medium into the carbinols is observed.

119 1) for the formation of a syn spiromethylene carbinol, K(m) 7 microM).

120 urants included ethyl acetate, acetyl methyl carbinol, methylhexanoate, sabinene, p-cymene, methylben

121 he parent ketone afforded the diastereomeric carbinol mixture which showed reduced inhibitory potency

122 paB (NF-kappaB), we postulated that indole-3-carbinol must mediate its activity through NF-kappaB mod

123 n to other metabolic products, the 8'-methyl carbinols of these N7-methyl-8-methylxanthines are forme

124 (NA) moiety in NAADP to either an uncharged carbinol or from the 3-position to the 4-position of the

125 , the absolute configuration of the original carbinol (or amino) stereocenter can be reliably deduced

126 intramolecular isotope effects; however, the carbinol oxygen is derived exclusively from molecular ox

127 ein interaction studies showed that indole-3-carbinol perturbs the auxin-dependent interaction of Tra

128 ere we examined the hypothesis that indole-3-carbinol plays a role in influencing plant growth and de

129 bearing an acetal group at the 5-position or carbinol position, or a dipyrromethane-1,9-dicarbinol be

130 -1,9-dicarbinol bearing an acetal group at a carbinol position.

131 ed a large coupling constant between vicinal carbinol protons.

132 earrangement of the alpha-hydroxycyclopropyl carbinols provides access to both cis- and trans-2,3-dis

133 We show that indole-3-carbinol rapidly and reversibly inhibits root elongation

134 a diverse set of functionalities in the aryl carbinol region.

135 es that are induced in the plant by indole-3-carbinol remain relatively uninvestigated.

136 ddition of the plant-derived ligand indole-3-carbinol rescued the barrier deficiency even in aged mic

137 ry was suggested, as application of indole-3-carbinol rescues auxin-induced root phenotypes.

138 e and 0.997, 0.42mg/L, 1.29mg/L for indole-3-carbinol, respectively.

139 xa-1,3-dienes upon acid-promoted cyclopropyl carbinol ring opening.

140 uced 99% pure S-(-)-1-isoquinolyl tert-butyl carbinol [(S)-16].

141 tage that the alpha- and beta-stereoisomeric carbinol series can be obtained on demand.

142 However, during storage indole-3-carbinol slowly degraded to 0.68 mumol/100 g FW, while a

143 Carbinol substituents determine the extent of cyclopropy

144 in the case of the less hindered aryl alkyl carbinol substrates.

145 Because of the ubiquity of the secondary carbinol subunit, the development of new methods for its

146 We demonstrated that indole-3-carbinol suppressed constitutive NF-kappaB activation an

147 Indole-3-carbinol suppressed constitutive NF-kappaB activation in

148 y enriched and functionally complex tertiary carbinols that may be easily accessed.

149 rise to degradation products (e.g., indole-3-carbinol) that can enhance tumorigenesis.

150 enerated ketone group into the corresponding carbinol, the effect of a number of different acidic con

151 With o-substituted aryl alkyl carbinols, the enantioselectivities exceed 100, and s =

152 secondary alcohols (specifically, aryl alkyl carbinols) through enantioselective acylation, and we su

153 n (1b) was selectively alkylated at the C-32 carbinol, thus providing esters and amides of 32-ascomyc

154 nding carbinol, and self-condensation of the carbinol to form the porphyrin.

155 dition of the natural phytochemical indole-3-carbinol to the purified diet.

156 ning cyclization of (hetero)aryl cyclopropyl carbinols to form alpha-alkylidene-gamma-butyrolactones

157 (i.e., those derived from conjugation of the carbinol under interrogation with MTPA) display differen

158 However, the introduction of carbinol units required the development of new building

159 The content of sulforaphane and indole-3-carbinol varied between 72+/-9-304+/-2mg and 77+/-1-117+

160 Indole-3-carbinol was an exceptionally potent AHR agonist (EC50 a

161 Several aryl pyridyl carbinols were obtained in high yields.

162 ethanol to the corresponding trichloromethyl carbinol with complete stereochemical fidelity, despite

163 cyclopropanation to afford aminocyclopropyl carbinols with three continuous stereocenters in a one-p