ライフサイエンスコーパス: hydantoin

1 mide, urea, guanidine, 2-aminoimidazole, and hydantoin.

2 ighly substituted, pharmaceutically relevant hydantoins.

3 the ongoing optimization of antischistosomal hydantoins.

4 followed by a base-catalyzed cyclization to hydantoins.

5 ructural context affects OG oxidation to the hydantoins.

6 rther proof of DprE1 being the target of the hydantoins.

7 ffords a straightforward entry to diarylated hydantoins.

8 erted to regiosiomeric mixtures of tricyclic hydantoins.

9 The aryl hydantoin 1 (Ro 13-3978) was identified in the early 198

10 dium channel binding activity (log IC50) for hydantoins 1-12 and diphenylhydantoin (DPH) (r2 = 0.638)

11 Hydantoin 13 had excellent selectivity over other zinc m

12 through structure-based drug design to give hydantoin 13.

13 ict literature sodium channel activities for hydantoins 14-20, which were not included in the trainin

14 -1,3,4-oxadiazole (24) and a phenylmethylene hydantoin (28), both exhibited nanomolar affinity and se

15 d-catalyzed enantioselective allylation of a hydantoin, achieved on gram scale in high yield and enan

16 addition of a second functional group at the hydantoin amide position (R(2)) converts the proline rin

17 esence of amines, G or OG oxidation produces hydantoin amine adducts.

18 n of 5-(3,4-dichlorophenyl) methylhydantoin (hydantoin), an antiviral drug that inhibits the replicat

19 aldol reaction between a suitably protected hydantoin and an optically enriched alpha-chloroaldehyde

20 two prebiotically plausible building blocks, hydantoin and glyoxylate, generates both the nucleobase

21 ional theory calculations revealed that both hydantoin and MeOH are crucial for the generation of cat

22 bypass lesions found in ancient DNA, such as hydantoins and abasic sites.

23 from two chemical classes, spirosuccinamide/hydantoins and carboxylic acids.

24 rolyzed and oxidatively deprotected to yield hydantoins and unsaturated alpha-quaternary amino acids.

25 including ureas, carbamates, thiocarbamates, hydantoins, and oxazolidinones.

26 tion is inhibited by primary amides, imides, hydantoins, and secondary cyclic amides, which are bypro

27 neration series of highly potent spirocyclic hydantoin antagonists of LFA-1.

28 scovered through structural modifications of hydantoin antiandrogens.

29 milar extent as sorbinil, a poorly selective hydantoin ARI previously shown to prevent retinopathy in

30 iomerically pure, systematically substituted hydantoins as structural privileged universal mimetic sc

31 HQD)(2)PHAL, employing various N-chlorinated hydantoins as the terminal chlorenium source.

32 n-associated antigen-1 (LFA-1) of a class of hydantoin-based antagonists of leukocyte cell adhesion h

33 The long half-lives of early hydantoin-based EBP inhibitors in rodents prompted an un

34 e previously discovered and profiled a novel hydantoin-based family that demonstrated highly promisin

35 BIRT377 (1, Figure 1), a previously reported hydantoin-based LFA-1 inhibitor, these compounds are cha

36 and X-ray analysis showed that the resulting hydantoin-based loops I (in particular) and II (to a les

37 12 years and includes the description of the hydantoin-based marketed drugs and clinical candidates.

38 olid state (X-ray) showed that the presented hydantoin-based peptidomimetics are able to project thei

39 erature compound 1 led to the discovery of a hydantoin-based scaffold, which provided balanced physic

40 opment of applications of N,N'-disubstituted hydantoin bearing alpha-amino acids by improving yields,

41 otein by the hydantoins, indicating that the hydantoin-binding site resides on the I-domain.

42 Furthermore, these quaternary hydantoins can be chemically manipulated to yield the co

43 A variety of hydantoins can be formed effectively under mild reaction

44 Hydantoins can be synthesized from the corresponding ami

45 e of a given chiral imidazolidine-2,4-dione (hydantoin) can be converted almost quantitatively into t

46 cause phenytoin and dantrolene belong to the hydantoin class of compounds, we test the hypothesis tha

47 Finally the hydantoin CoMFA model was used to design the structurall

48 Hydantoins containing trienes and tetraenes undergo sele

49 inct from the previously described series of hydantoin-containing indole derivatives (Nec-1), the Nec

50 A short synthesis of the hydantoin-containing marine sponge metabolites axinohyda

51 Three hydantoin-containing natural products including macahyda

52 The principal SAR insight was that the hydantoin core of 1 is required for high antischistosoma

53 no acid-based core structure, derived from a hydantoin core, with unique heterocycles on the side cha

54 own hydantoinases for D-5-(2-methylthioethyl)hydantoin (D-MTEH) over the L-enantiomer leads to the ac

55 r rearrangement pathway to the corresponding hydantoin derivative competes with HNO formation, partic

56 Dantrolene sodium is a medically important hydantoin derivative that interferes with release of Ca2

57 Phenytoin is a hydantoin derivative that is used clinically for the tre

58 metathesis to produce a functionalized fused hydantoin derivative.

59 elop an informative mathematical model using hydantoin derivatives as a training set of substrates by

60 A series of hydantoin derivatives have been prepared as single isome

61 e resulting urea to give bicyclic alpha-aryl hydantoin derivatives of substituted prolines.

62 5-Substituted-3-(alkoxycarbonyl)alkyl-hydantoin derivatives were prepared by mechanochemistry

63 s resulted in the first reported examples of hydantoin derivatives with good PK in preclinical specie

64 ation of this strategy to the development of hydantoin-derived aggrecanase inhibitors (eg, 3) for the

65 d with a hydantoin triene to give a bicyclic hydantoin dimer in high yield.

66 o occur from only one but not from the other hydantoin enantiomer.

67 Subsequent tautomerization leads to both hydantoin enantiomers, but only one of them returns to t

68 Overall, the hydantoin family of DprE1 inhibitors represents a promis

69 nificant barriers (10 kcal/mol), while fused hydantoins (five-membered fusion) have barriers that are

70 rds quaternary 5,5-(aryl, allyl)-substituted hydantoins found in many biologically significant compou

71 e approach to the synthesis of 5-(indol-3-yl)hydantoin framework has been developed by the reaction o

72 brane protein for sodium-linked transport of hydantoins from Microbacterium liquefaciens.

73 for the preparation of enantiomerically pure hydantoins from optically pure alpha-amino amides utiliz

74 However, NEIL1, NEIL2 and NEIL3 remove hydantoins from telomeric quadruplexes formed by five TT

75 ndly preparation of 5- and 5,5-disubstituted hydantoins from various amino ester hydrochlorides and p

76 The tolerance of the hydantoin group to the selenoxide elimination reaction c

77 inoalkyl group could be added to the central hydantoin group without significantly affecting binding.

78 OG), and its further oxidation products, the hydantoins guanidinohydantoin (Gh) and spiroiminodihydan

79 These aryl hydantoins had good in vitro ADME profiles, with calcula

80 protocol is general, and various N-arylated hydantoins have been prepared in excellent yields with e

81 g an aspartic acid motif embedded in a rigid hydantoin heterocycle are synthesized through a sequenti

82 The biologically relevant hydantoin (imidazolidinedione) heterocycle functions as

83 Secondary amides afford the hydantoins in good to excellent yields, which decrease a

84 ino esters, in smooth conditions, leading to hydantoins in good yields and with no need of purificati

85 microwave irradiation in aqueous media gives hydantoins in high yields, further demonstrating the abi

86 ey can be converted to unsymmetric ureas and hydantoins in high yields.

87 from binding to the purified protein by the hydantoins, indicating that the hydantoin-binding site r

88 e, potent, and safe non-carboxylic acid, non-hydantoin inhibitor of aldose reductase (AR) capable of

89 A series of hydantoin inhibitors of ADAMTS-4 and ADAMTS-5 were ident

90 nd highly selective non-carboxylic acid, non-hydantoin inhibitors of AR yet described (IC50, 1 nM; ED

91 is involved in virus encapsidation and that hydantoin inhibits this stage of replication.

92 m indicated that selective N(3)-arylation of hydantoin is favorable in MeOH, which helps initiate the

93 on of imidazolones to alpha,beta-unsaturated hydantoins is outlined and represents a new approach to

94 applicable procedures for the N-arylation of hydantoins is reported.

95 ubstituted 3-phenylimidazolidine-2,4-diones (hydantoins) is reported (27 examples, 69%-quant., 80-99%

96 ther sodium ions or the substrate 5-benzyl-l-hydantoin (L-BH) does not shift this conformational equi

97 Interestingly, a hydantoin lesion at the site most prone to oxidation in

98 te specificity with hNEIL1 revealed that the hydantoin lesions are excised much more efficiently (>10

99 These results indicate that the hydantoin lesions are the best substrates identified thu

100 NEIL1 and NEIL3 DNA glycosylases can remove hydantoin lesions but none of the glycosylases, includin

101 pathways mediate repair of a diverse set of hydantoin lesions in cells.

102 However, removal of hydantoin lesions in the absence of an opposite base may

103 Hydantoin lesions produced from further oxidation of 8-o

104 , the excision efficiency by hNEIL1 of these hydantoin lesions relative to other known substrates was

105 y and efficient activity of EcFpg toward the hydantoin lesions suggest that EcFpg mediates repair of

106 nce of the helix-destabilizing nature of the hydantoin lesions that facilitates their recognition wit

107 ) with a wide variety of oxidants yields the hydantoin lesions, guanidinohydantoin (Gh) and spiroimin

108 Of these, the hydantoin lesions, guanidinohydantoin (Gh) and the two d

109 quire a base opposite to identify and remove hydantoin lesions.

110 was successful in designing an effective non-hydantoin ligand.

111 are recognised through hydrogen bonds to the hydantoin moiety and the complementarity of the 5-substi

112 f the hydrazine allowed the preparation of a hydantoin motif bearing an aminopropyl side chain, which

113 tures of the dimetal TnDhp in complexes with hydantoin, N-carbamyl-beta-alanine, and N-carbamyl-beta-

114 ally accessible, the corresponding N(1)-aryl-hydantoin-N(3)-oxyl radical showed significantly higher

115 that led to a structurally unprecedented non-hydantoin, non-carboxylic acid aldose reductase inhibito

116 not sufficient to account for the effects of hydantoins on the NVSC.

117 guanine (5-HO-OG) partitioning along the two hydantoin pathways, allowing us to propose a mechanism f

118 l member of the NCS1 family, the Mhp1 benzyl-hydantoin permease from Microbacterium liquefaciens, all

119 However, this series of aryl hydantoins produced antiandrogenic side effects in the h

120 The hydrolysis of the hydantoin products provides derivatives of quaternary am

121 to further oxidation to the highly mutagenic hydantoin products spiroiminodihydantoin (Sp) and 5-guan

122 Derivatives of 4-hydantoin-proline have been synthesized via a direct two

123 a double Mitsunobu reaction using a pyrrole hydantoin provided the putative structure of nagelamide

124 to prepare enantioenriched 5,5-disubstituted hydantoins (quaternary hydantoins), which are medicinall

125 d L-hydantoinase, an L-N-carbamoylase, and a hydantoin racemase produced 91 mM L-met from 100 mM D,L-

126 HAT does not occur to the carbon atom of the hydantoin radical but to its oxygen atom.

127 Replacement of the phenol ring with a hydantoin resulted in weak antagonists.

128 In order to understand the importance of the hydantoin ring for good sodium channel binding, related

129 Two major conclusions were drawn: (1) The hydantoin ring is not critical for compounds with long a

130 Next, we noted the hydantoin ring of dGh mimics thymine, while the iminohyd

131 The perpendicular hydantoin ring of Gh is stabilized by noncanonical lone

132 econfiguration of the Gh lesion in which the hydantoin ring rotates ~90 degrees and is perpendicular

133 the four possible points of diversity in the hydantoin ring.

134 and serves to control the orientation of the hydantoin ring.

135 itor obtained by optimization of a promising hydantoin series following an HTS.

136 n performed on a 4-methyl-4-(4-hydroxyphenyl)hydantoin series is described which resulted in the deve

137 ed volume as key contributing factors in the hydantoin series while correctly predicting the experime

138 ntional five-step solid-phase synthesis of a hydantoin, similar results were obtained for both the H-

139 xidation of 8-oxoG leads to the formation of hydantoins, specifically guanidinohydantoin (Gh) and spi

140 nctional groups (67-84% yields from a common hydantoin starting material) as well as a spiroligomer t

141 Novel synthetic routes to various hydantoin structures, the advances brought to the classi

142 mploying 5-membered heteroaromatic groups as hydantoin substituents to become more potent on ADAMTS7.

143 We show precisely where 5-substituted hydantoin substrates bind in an extended configuration a

144 for good sodium channel binding, related non-hydantoins such as hydroxy amides, oxazolidinediones, hy

145 enantio- and diastereoselective addition of hydantoin surrogates II to "rigidified" vinylidene bis(s

146 he conformational cycle of the Na(+)-coupled hydantoin symporter Mhp1 from Microbacterium liquefacien

147 latter specifically in the setting of foetal hydantoin syndrome.

148 The review highlights the hydantoin syntheses presented from the point of view of

149 lar N-to-C aryl migration, yielding bicyclic hydantoins that can be further hydrolysed to afford quat

150 An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were

151 sformed in enantioenriched 5,5-disubstituted hydantoins through hydrolysis and reductive desulfonylat

152 iminary 3-D QSAR model for the binding of 14 hydantoins to the neuronal voltage-gated sodium channel;

153 The hydantoin transporter Mhp1 is a sodium-coupled secondary

154 e substrate-bound structures of CodB and the hydantoin transporter Mhp1, the only other NCS1 family m

155 trom resolution structure of the NCS1 benzyl-hydantoin transporter, Mhp1, from Microbacterium liquefa

156 els of full-length plus-strand virion RNA in hydantoin-treated cultures.

157 to match side-chain orientations of a novel hydantoin triazole chemotype (1) to protein-protein inte

158 oss metathesis (RC-RO-RC-CM) occurred with a hydantoin triene to give a bicyclic hydantoin dimer in h

159 The hydrolysis of the bicyclic hydantoins under basic conditions gave a range of enanti

160 nder optimized conditions, an array of (thio)hydantoins was readily prepared, and an enantioselective

161 As exemplified by Ro 13-3978 (1), aryl hydantoins were identified in the early 1980s as a promi

162 hed 5,5-disubstituted hydantoins (quaternary hydantoins), which are medicinally important compounds b

163 open by an inhibitor, 5-(2-naphthylmethyl)-L-hydantoin, which becomes a substrate when leucine 363 is

164 roteins that together catabolize substituted hydantoins, whose chemical structure resembles that of a

165 he amino acid, followed by ring closure to a hydantoin with concomitant explulsion of the recyclable

166 An efficient and practical N-arylation of hydantoins with substituted aryl/heteroaryl boronic acid

167 Comparisons among different hydantoins with the same log P but different low-energy