ライフサイエンスコーパス: sulfamate

1 lfatase inhibitors, most notably estrone-3-O-sulfamate.

2 ide, LNA-carbamate, LNA-alkoxyamide, and LNA-sulfamate.

3 ers of magnitude, from 1.3 to 600 microM for sulfamate.

4 inhibitors of CA-II than their corresponding sulfamates.

5 nosine 5'-monophosphate-mimicking nucleoside sulfamates.

6 ar aziridination of substituted alkenes with sulfamates.

7 , 1,3-enynes, and imines to give homoallylic sulfamates.

8 exchange method to access organosulfates and sulfamates.

9 me-catalyzed hydrolysis of aryl sulfates and sulfamates.

10 method is also amenable to access N-thioacyl sulfamates.

11 The hydrolysis of N-methyl O-phenyl sulfamate (1) has been studied as a model for steroid su

12 onditions are presented for detection of the sulfamate (1)H NMR resonances in aqueous solution.

13 Boc anhydride provided the activated cyclic sulfamates 13 and 14.

14 The most promising sulfamates 13, 16, 18-20, 22-24, 36, and 37 showed nanom

15 l (2-MeOE2), 2-methoxyestradiol-3,17-O,O-bis-sulfamate (2-MeOE2bisMATE), has shown potent antiprolife

16 ated estrone derivative 2-methoxyestrone-3-O-sulfamate (2-MeOEMATE) induced G2-M cell cycle arrest an

17 X-ray analysis of the major diastereomer of sulfamate 21a.

18 gents, 2-ethylestrone and 2-ethylestrone-3-O-sulfamate (2EtEMATE).

19 r as an STS inhibitor compared to parent bis-sulfamate 3.

20 2-ethylestradiol-3,17-O,O-bis-sulfamate 4 GI(50) = 0.21 microM).

21 , comparable to letrozole), whereas the ( S)-sulfamate, ( 40b) inhibited STS most potently (IC 50 = 5

22 d 2-ethyl derivative 7, and the related 3- O-sulfamates 8 and 15 display potent antiproliferative eff

23 reaction can be performed with two different sulfamates, a process that offers the opportunity to dif

24 lective allylic C-H oxidation of unsaturated sulfamates, a property not observed with other dirhodium

25 ide Pin1 inhibitor to a potent and selective sulfamate acetamide with improved buffer stability.

26 These findings introduce sulfamate acetamides as a new class of covalent nsP2 pro

27 Finally, we show that sulfamate acetamides can be used for covalent ligand-dir

28 chanism-based pan-E1 inhibitor, adenosine 5'-sulfamate (ADS), reacted with the Uba5 approximately Ufm

29 MLN4924 is an adenosine sulfamate analogue that was identified as a selective, m

30 ion of human UAE (Ube1) by another adenosine sulfamate analogue, 5'-O-sulfamoyl-N(6)-[(1S)-2,3-dihydr

31 e substrate-assisted inhibition by adenosine sulfamate analogues represents a promising strategy to d

32 the context of the BTK inhibitor ibrutinib, sulfamate analogues showed low reactivity with comparabl

33 oids corrected herein each contain an indole sulfamate and are all carbon-bridged dibrominated bis-in

34 s the relative effectiveness of bioisosteric sulfamate and sulfamide derivatives for inhibition of hu

35 paper examines the relative effectiveness of sulfamate and sulfamide groups for the inhibition of car

36 e, an indolo[3,2-a]carbazole also possessing sulfamate and sulfate groups, was isolated from two sepa

37 es A-C and bis-ancorinolate B, which contain sulfamate and sulfate groups, were isolated from the aqu

38 e identifying potential interactions for the sulfamate and the peptide backbone with Arg2849 and Asn2

39 talyzed Suzuki-Miyaura-type coupling of aryl sulfamates and boronic acid derivatives enabled by tempe

40 ki-Miyaura coupling reactions involving aryl sulfamates and boronic acids, which operates at a signif

41 A IX-mimic in complex with selected glucosyl sulfamates and structurally rationalize mechanisms for h

42 f intramolecular aza-Michael cyclizations of sulfamates and sulfamides onto pendant alpha,beta-unsatu

43 a sizable difference in potency between the sulfamates and sulfamides, with the sulfamides being muc

44 reaction and was inhibited by sulfonamides, sulfamates, and sulfamides with K(I) in the nanomolar to

45 pileptic drug topiramate (1), a unique sugar sulfamate anticonvulsant that was discovered in our labo

46 (ii) the catalytic intermediate (dppf)Ni(Ar)(sulfamate) (Ar = aryl) undergoes comproportionation with

47 Organosulfates and sulfamates are important classes of bioactive molecules

48 xide, sulfone, oxazolidinone, carbamate, and sulfamate--are found to engage in this reaction to give

49 We identified adenosine 5'-sulfamate as a broad-specificity compound that hijacks a

50 ew class of CA IX inhibitors that comprise a sulfamate as the zinc binding group, a variable linker,

51 r diamination of acrylates is reported using sulfamates as nitrogen sources.

52 accessible phenolic derivatives such as aryl sulfamates, as the sulfamate moiety can act as a directi

53 sts, we examined the reaction of N-neopentyl sulfamate at elevated temperatures and found it to under

54 erocyclic strained cyclooctynes containing a sulfamate backbone (SNO-OCTs) were prepared under mild c

55 general method of stabilizing and delivering sulfamate-based drugs in vivo.

56 We report sulfamate-based electrophiles that maintain chloroacetam

57 e pyrophosphate and the terminal ribose by a sulfamate-based group leads to a weak antagonist, a lead

58 Simple sulfonamides and sulfamates can be used directly in the reaction without

59 le aryl chlorides, mesylates, tosylates, and sulfamates can be used to yield the same branched produc

60 amides, ester, sulfoxides, unactivated aryl sulfamates, carbamates, pivalates, as well as novel elec

61 l of compounds belonging to the underexposed sulfamate class of carbonic anhydrase (CA, EC 4.2.1.1) i

62 CA inhibitors of the sulfamate class specifically targeting the tumor-associa

63 r these bioisosteric pairs, 1/4 and 6/5, the sulfamate compound was markedly more potent than its sul

64 es the formation of an inhibitory amino acid-sulfamate conjugate through a reaction-hijacking mechani

65 nates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electro

66 fferent types of binding particularly in the sulfamate-containing aromatic ring and the opposite geom

67 recently been implicated in the delivery of sulfamate-containing drugs.

68 Both biphenyls share a para-sulfamate-containing ring B and a ring A, which contains

69 h nucleophilic ring-opening reactions of the sulfamate core.

70 of electrophiles, were used to construct the sulfamate core.

71 ethoxyestra-1,3,5(10)-triene (STX140), a bis-sulfamate derivative of the endogenous steroid 2-methoxy

72 es of a series of steroidal and nonsteroidal sulfamate derivatives against CA IX in comparison to the

73 Inhibitory activity of the sulfamate derivatives against steroid sulfatase and carb

74 figured 2,3-diamino carboxylates as bicyclic sulfamate derivatives.

75 gues of 2-substituted estradiol-3,17-O,O-bis-sulfamates (E2bisMATEs) are discussed.

76 iridines; unsubstituted, N-alkyl, and N-aryl sulfamates engage effectively.

77 rocycles are prepared through intramolecular sulfamate ester C-H insertion with a Rh(2+)-carboxylate

78 The interaction of a sulfamate ester derived metallonitrene with an allene ge

79 Specifically, we determine that sulfamate ester derived nitrogen-centered radicals media

80 The reaction of a sulfamate ester derived rhodium nitrenoid species with a

81 Herein, an alcohol-derived sulfamate ester guides the light-initiated xanthylation

82 modification to both the nitrogen source, a sulfamate ester, and substrate are shown to impact isome

83 odel has informed the development of a novel sulfamate ester, which affords the highest benzylic-to-t

84 s via masking their phenolic OH group with a sulfamate ester.

85 that is guided by a pendant alcohol-anchored sulfamate ester.

86 lyzed C-H insertion of hydroxylamine-derived sulfamate esters makes possible the synthesis of unique

87 sulfatase PaAstA catalyzes the hydrolysis of sulfamate esters with catalytic rate accelerations of ~1

88 es and cycloalkane/linear alkane moieties in sulfamate esters, such as those derived from menthane an

89 ceutical relevance, including sulfamides and sulfamate esters.

90 allylic C-H amination with bis(homoallylic) sulfamate esters.

91 asymmetric, intramolecular C-H amination of sulfamate esters.

92 The efficiency of mesylates, sulfamates, esters, carbonates, carbamates, and methyl e

93 ly simple method for the synthesis of N-acyl sulfamates from fluorosulfonates and potassium trimethyl

94 The sulfamate group (1)H and (15)N chemical shifts of six GA

95 parinux demonstrate the broad utility of the sulfamate group (1)H chemical shifts to reflect differen

96 tance of several molecular features: (1) the sulfamate group (6-8, 22-25, 27, 84), (2) the linker bet

97 ected aniline and telescoped cleavage of the sulfamate group after amination leads directly to ortho-

98 , 22-25, 27, 84), (2) the linker between the sulfamate group and the pyran ring (9, 10, 21a,b), (3) t

99 id sulfatase inhibitors (DASIs) containing a sulfamate group are now being developed.

100 he sulfamide group is less suitable than the sulfamate group for obtaining potent inhibition of CA-II

101 nucleophilic attack of UAE thioester by the sulfamate group of Compound I after completion of step 2

102 t remove two rotatable bonds and the ionized sulfamate group on the basis of computational and struct

103 nthetically versatile aryl O-carbamate and O-sulfamate groups are described.

104 s with a combination of 2,2,2-trichloroethyl sulfamate (H(2)NTces), (diacetoxyiodo)benzene (PIDA), an

105 ons (CHB) of tetraalkylammonium sulfates and sulfamates have been achieved using bipyridine-ligated I

106 oylated 2-alkylestradiol-17-O-carbamates and sulfamates have considerable potential as anticancer age

107 n the liberation of the phenolic compound by sulfamate hydrolysis and 17beta-HSD1 inactivation.

108 Type I sulfatases are inactivated by aryl sulfamates in a time-dependent, irreversible, and active

109 lyzed amination of two C(sp(3))-H bonds with sulfamates in the presence of a potent iodine(III) oxida

110 ereby illustrating the higher versatility of sulfamates in these cycloadditions.

111 nates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature.

112 bilities of various proposed end-products of sulfamate-induced sulfatase inactivation highlights that

113 Estradiol-3,17-O,O-bis-sulfamates inhibit steroid sulfatase (STS), carbonic anh

114 Recently, the use of glucosyl sulfamate inhibitors has shown promise as selective inhi

115 duction sequence converts simple homoallenic sulfamates into densely functionalized aminated cyclohep

116 laboratory, it was reported that estrone-3-O-sulfamate irreversibly inhibits a new potential hormone-

117 The ring opening of aziridines by pendant sulfamates is a viable strategy for the rapid preparatio

118 oss-couplings of carbamates, carbonates, and sulfamates is described.

119 ind that a library of aryl- and carbohydrate sulfamates is ineffective against carbohydrate sulfatase

120 iridination of silyl-substituted homoallenic sulfamates is readily diverted to the distal double bond

121 nd an inhibition study with sulfonamides and sulfamates led to the detection of a large number of low

122 The LNA-sulfamate linkage is of particular interest, forming ver

123 x (unmetabolized plus the N2-glucuronide and sulfamate metabolites) excreted in the 0-12 h urine was

124 x (unmetabolized plus the N2-glucuronide and sulfamate metabolites) in urine was associated with high

125 loride, sulfate, nitrate, nitrite, chlorate, sulfamate, methanesulfonate, and fluoride, which can be

126 The sulfamate microenvironments characterized in this study

127 idazoles incorporating sulfonamide/sulfamide/sulfamate moieties were designed and synthesized as radi

128 derivatives such as aryl sulfamates, as the sulfamate moiety can act as a directing group for the pr

129 ydrolysis by an S(N)2 mechanism whereas aryl sulfamate monoanions follow an S(N)1 pathway with SO2NH

130 of the (1)H and (15)N chemical shifts of the sulfamate NH groups for the structural characterization

131 Sulfamate (NHSO(3)(-)) groups are critically important s

132 e to the active site zinc(II) atom via their sulfamate nitrogen, while the rest of the molecule is co

133 an inconvenient aryl or amide linker at the sulfamate nitrogen.

134 The oxidative addition with carbamates or sulfamates occurs via a five-centered transition state,

135 rozole derivatives were prepared bearing bis-sulfamates or mono-sulfamates with or without adjacent s

136 Thioxolone lacks sulfonamide, sulfamate, or hydroxamate functional groups that are typ

137 The aryl sulfamate pharmacophore is highly versatile, operating v

138 ts were initiated to develop the core aryl O-sulfamate pharmacophore that, over some 20 years, have l

139 The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of t

140 The sulfamate protons also provide an efficient route for de

141 C-2 Substitution and 17-sulfamate replacement of the estradiol-3,17-O,O-bis-sulf

142 ples with N-ethylmaleinimide and/or ammonium sulfamate, respectively.

143 as well as in the subsequent opening of the sulfamate ring once it has been installed in the polymer

144 4-(3'-(3'',5''-dimethylphenyl)ureido)phenyl sulfamate (S4), was taken forward into the orthotopic MD

145 conversion of the substrates into sulfate or sulfamate salts, wherein the anionic arene component is

146 In the sulfamate series a number of permutations of linker and

147 tegy relies on the use of proximal halide or sulfamate substituents to perturb pyridyne distortion, w

148 ference in potency was also observed for the sulfamate/sulfamide pairs 14/15 and 16/17.

149 Compounds 1-10, which represent five cognate sulfamate/sulfamide pairs, were studied by ThermoFluor t

150 lation, and an efficient cyclotryptamine-C3a-sulfamate synthesis by either a new silver-promoted nucl

151 ined catalytic pocket, with tert-butylphenol sulfamate (TBPhsNH(2)), which leads to a discriminating

152 Our route uses a sulfamate-tethered aza-Wacker cyclization as a key step

153 ey step in the synthesis is our laboratory's sulfamate-tethered aza-Wacker cyclization.

154 gets for a class of AMP-mimicking nucleoside sulfamates that target the enzymes via a novel reaction

155 With the exception of mesylates and sulfamates the efficiency of all other 2-naphthyl C-O el

156 ntified acetamide inhibitors bearing N-alkyl sulfamate warheads with improved biochemical and antivir

157 th the two C-O electrophiles, mesylates, and sulfamates was compared.

158 A novel synthetic strategy toward N-acyl sulfamates was developed.

159 ith amides, a wide and diverse set of N-acyl sulfamates was synthesized, including functionalized bio

160 te replacement of the estradiol-3,17-O,O-bis-sulfamates were explored with efficient and practical sy

161 The sulfamates were intentionally designed as drugs for the

162 by sulfanilamide and (5-methylisoxazol-3-yl)-sulfamate, whereas at pH 3, a photoisomer was the domina

163 = 0.38 microM) as the most active novel bis-sulfamate, while 2-ethyl-17-carbamate derivative 52 (GI(

164 The combination of a tailored sulfamate with a C(4)-symmetrical rhodium(II) tetracarbo

165 were prepared bearing bis-sulfamates or mono-sulfamates with or without adjacent substituents.

166 amination-oxidation sequence or to hydrazine sulfamate zwitterions by an unusual N-amination.