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1 ance stabilized iminoquinone (i.e., extended amidine).
2 cyclization to form the corresponding cyclic amidine.
3 ylamide are good alternatives for the second amidine.
4 f the second generation PAD inhibitor, BB-Cl-amidine.
5 sosteres for the parent pan PAD inhibitor Cl-amidine.
6 oduce five-, six-, and seven-membered cyclic amidines.
7 robic [3+2]-annulation reaction of N-alkenyl amidines.
8 ore the remarkable behavior of the residue 4 amidines.
9 pre-organized for a fit to the heterocyclic amidines.
10 e reduced binding to DNA relative to similar amidines.
11 ial relationship with the groove relative to amidines.
12 azoles in the preparation of polysubstituted amidines.
13 azole-biphenyl isomers with terminal charged amidines.
14 hesize 1,3,5-trizines from acetophenones and amidines.
15 d sulfonamide enables efficient synthesis of amidines.
24 ifluoromethyl-4-iodo-nicotinic acid (2) with amidine 9a catalyzed by Pd(2)(dba)(3) and Xantphos, foll
26 2-chloro-1-iminoethyl)-L-ornithine amide (Cl-amidine), a recently described pan-PAD inhibitor, could
27 that inhibition of PAD enzyme activity by Cl-amidine, a pan-PAD inhibitor, blocks NLRP3 inflammasome
30 rted the synthesis and characterization of F-amidine, a potent and bioavailable irreversible inactiva
33 transformation of the 5-cyano group into an amidine allows synthesis of 2,5-terpyrimidinylenes with
34 potent PAD4 inhibitors, we show here that Cl-amidine also exhibits a strong inhibitory effect against
38 f mechanistic studies of NOS inactivation by amidine analogues of l-arginine and other previous mecha
40 We confirmed survival-improving effect of Cl-amidine and are the first to explore the role of Cl-amid
41 investigation of the activity of a series of amidine and bisamidine compounds against Staphylococcus
42 ir assessment indicates that combined pocket amidine and CBP peripherally modified analogues exhibit
43 novel and diverse compounds based on cyclic amidine and guanidine cores were synthesized with the go
47 zed oxidative cyclization of 2-aminopyridine/amidine and isothiocyanate via N-S bond formation at amb
48 ICs = 0.06-0.005 and 0.5-0.06 mug/mL for the amidine and methylene analogues, respectively) and likel
49 phase behavior and microstructure of diC(14)-amidine and of the lipid/DNA (circular plasmid, 5.4 kb)
51 cin stems from its unprecedented macrocyclic amidine and rare beta-methylated amino acid residues.
54 m exchanges in the binding pocket (residue 4 amidine and thioamide) are disclosed as well as their pe
55 ssover reactivities (1,2,4,5-tetrazines with amidines and 1,2,3,5-tetrazines with strained dienophile
61 to the formation of the corresponding cyclic amidines and guanidines, typically in good to excellent
62 he first time the development of phosphonate amidines and sulfonate amidines as isosteres of pArg and
63 riles (YMs) react with amines to form cyclic amidines and that the starting linear YMs are nonemissiv
65 emonstrated by 33 examples with a variety of amidines and three different 4H-pyrido[1,3]oxazin-4-one
67 ion with substituents between the vinylogous amidine, and hydrolytic properties that can be controlle
68 mall molecules and macromolecules containing amidine, and to a lesser extent, guanidine functional gr
69 vided by a benzimidazole (or indole) -NH and amidines, and (iii) appropriate curvature of the dimer c
72 al proteins observed in mice treated with Cl-amidine are consistent with the notion that Cl-amidine d
79 opment of phosphonate amidines and sulfonate amidines as isosteres of pArg and then use these mimics
81 oxylation step during inactivation of NOS by amidines as well as the HO-catalyzed reaction, the essen
82 interaction of a key compound, which has the amidine at the phenyl shifted from the para position in
83 itively charged group such as an amine or an amidine at this position results in improved affinity fo
84 ensation of 4H-pyrido[1,3]oxazin-4-ones with amidines at room temperature or under microwave irradiat
85 rom PFAA-enamine cycloadditions rearrange to amidines at room temperature, while (3 + 2) cycloadditio
87 col substituted phthalocyanines utilizing an amidine-base-promoted phthalonitrile tetramerization rea
90 : enantioselective acyl transfer promoted by amidine-based catalysts (ABCs) and a racemic chain mecha
94 to the discovery of a novel series of cyclic amidine-based inhibitors of beta-secretase (BACE-1).
103 oroaryl ring, and a phenyl ring linked by an amidine bond, were efficiently synthesized by a straight
104 conformer relative to rotation about the P-C(amidine)() bond; however, DFT calculations indicate a lo
105 a new, practical, and direct route to N-acyl amidines but also represents a new type of C-N bond form
106 containing natural products are converted to amidines by a C-H amination-oxidation sequence or to hyd
107 constitutes a bioorthogonal approach toward amidines by avoiding the use of amines and transition-me
108 o radius of curvature from amidine carbon to amidine carbon but a significant dihedral twist across t
109 ives for targeting the minor groove have the amidine carbon linked to a central heterocyclic system,
110 mpounds have a zero radius of curvature from amidine carbon to amidine carbon but a significant dihed
111 bstrate by hydrogen atom abstraction from an amidine carbon, the 5'-deoxyadenosyl radical abstracts h
115 orin associated to NI are consistent with an amidine-carboxylic acid interface, which is also verifie
117 oton to the carboxylate to form a nonionized amidine-carboxylic acid two-point hydrogen network, wher
119 ne) (14), has been reported to give a cyclic amidine complex when treated with 2 equiv of 2,6-dimethy
120 compounds, biphenyl tetrazole tert-butyl Cl-amidine (compound 13), exhibits enhanced cell killing in
123 ation of peptide sequence dependence of this amidine conjugation reveals a tripeptide tag CIS that al
127 ly observed for iNOS inactivation by another amidine-containing compound, N5-(1-iminoethyl)-L-ornithi
130 d on the basis of the N'-(4-halopyrazol-5-yl)amidine cyclization under the conditions of copper-catal
133 or the preparation of alpha,beta-unsaturated amidine derivatives appears to offer high yield, mild co
136 mechanisms of decomposition of guanidine and amidine derivatives in aqueous solution and the rate enh
137 ic guanidine, N-alkylguanidine, and reversed amidine derivatives of fused ring systems have been synt
138 d provides authentic residue 4 thioamide and amidine derivatives of the vancomycin aglycon that will
139 idine are consistent with the notion that Cl-amidine derives its efficacy from its ability to inhibit
142 ional bonding overlaps in the HOMO, and this amidine effect predicts lower N-inversion barriers in an
143 l-N'-tetradecylamino-propionamidine (diC(14)-amidine), efficiently ports DNA into mammalian cells in
145 h possesses the ethylene tether and extended amidine feature found in the pyrroloiminoquinone natural
146 we show the versatility of these vinylogous amidines for organic synthesis, including the following:
149 yield, presumably via novel Sn (IV)-mediated amidine formation from the initial aniline reduction pro
150 ary carboxamides exhibit different outcomes, amidine formation versus transamidation, depending on th
152 cules exist as zwitterions with a protonated amidine fragment of the eight-membered ring neutralizing
153 diamine tautomer of a variety of substituted amidine free bases reacts with nitric oxide (NO) to prod
154 ecarboxylation cascade synthesis of sulfonyl amidines from sulfonyl azides and substituted amides at
155 vestigation revealed that the in situ formed amidines from the coupling of benzylamines and nitriles
156 ystal, a solution of inhibitor containing an amidine functional group on a naphthalene ring was added
160 lation, which liberates the desired sulfonyl amidines, generating N2 and CO2 as the only reaction byp
161 ion of a hydroxyl group para to the proximal amidine group increases the potency vs fXa by 1-2 orders
163 te that substitution of the thiourea with an amidine group leads to greatly enhanced cytotoxicity in
164 Certain exogenous nucleobases that share the amidine group of adenine restored activity to abasic rib
165 ural and biochemical evidence implicated the amidine group of an active site adenosine, A38, in a pH-
167 f either carboxylic acid ligands through the amidine group or pyridine-type ligands through the Zn(II
168 interaction and a replacement for the distal amidine group that binds in the S3/S4 pocket of fXa.
169 terminal phenyl substituent on the reversed amidine groups as critical components in the strong bind
170 he new synthetic compounds have two aromatic-amidine groups for A/T recognition, and these are connec
173 ements indicate that the position of the two amidine groups on the carbazole ring influences signific
176 This tutorial review highlights the use of amidine, guanidine, and related isothiourea catalysts in
177 wis pair catalysts composed of a Lewis base (amidine, guanidine, or quaternary onium salts) and a Lew
178 l review is largely organized by the type of amidine/guanidine and transition metal used and covers l
179 ll nitrogen bases: nitriles, azoles, azines, amidines, guanidines, vinamidines, biguanides, and phosp
182 ns, but the linking group for the two phenyl amidines has a pK(a) of 6.3 that is susceptible to a pro
183 ethod for the synthesis of bi- and tricyclic amidines has been developed through copper-catalyzed aer
184 ne-pot domino reaction of 1,2-diketones with amidines has been identified that enables their transfor
186 ies of benzimidazole-based derivatives of Cl-amidine, hypothesizing that this scaffold would allow ac
187 the enzyme-bound structure of ZK-816042, an amidine-imidazoline inhibitor of human factor Xa (FXa).
191 lts were utilized to synthesize monoarylated amidines in moderate to high yields with ligand-free con
193 , a third mechanism is proposed in which the amidine inactivators of iNOS bind as does substrate L-ar
196 steric and leaving group requirements for F-amidine-induced PAD4 inactivation, the structure of the
198 alogue 2 can be used when the product cyclic amidine is organic-soluble, thus producing water-soluble
199 bonds of N-alkylamidines and N-(2-alkylaryl)amidines is described that utilizes the CuBr.SMe(2)/2,2'
203 echanisms of hydrogen exchange in amides and amidines led to the influence of hydrogen bonding and to
208 (2) abstraction of a hydrogen atom from the amidine methyl group followed by attachment to the heme
209 oes substrate L-arginine, but because of the amidine methyl group, the heme peroxy intermediate canno
210 etween the electronegative tip and guanidine-amidine moiety extends the conjugation and facilitates n
211 mical and structural analyses pinpointed the amidine moiety of base Ade38 as a key functional group i
212 the introduction of fluorine adjacent to the amidine moiety, resulting in in vivo brain reduction of
214 g at different sites of a (Zn)phthalocyanine-amidine molecule (Pc1), enables the dissociation of the
215 rd the Ala190 enzymes is observed due to the amidine N1 nitrogen of the bound inhibitor being deprive
220 involved water-mediated H-bonds between one amidine of the compound and DNA bases at the floor of th
221 ran that, when amplified out to the terminal amidines of the benzimidazole compounds, yields a very s
224 cooperative dimer to form but removal of one amidine or addition of an alkyl group to the amidine str
225 It was also demonstrated that the required amidine or iminocarbamate directing group fulfills two m
226 cribed here was the discovery of a novel bis(amidine) organocatalyst that provides high enantioselect
228 mpared with 2-PAM, the most promising cyclic amidine-oxime (i.e., 12e) showed comparable or greater r
233 t (i.e., 5 min after OP exposure, i.p,) with amidine oximes 7a-c and 12a, 12c, 12e, 12f, and 15b (145
236 istry of nine acyclic secondary and tertiary amidines (Ph-N=C(R(1))NR(2)R(3); R(1) = H, CH(3), Ph; R(
237 be lead optimization focused on reducing the amidine pKa while optimizing interactions in the BACE1 a
238 The nitro- or cyano-substituted guanidine/amidine planes of the neonicotinoids provide a unique el
239 Collectively, our results demonstrate Cl-amidine plays protective roles by significantly decreasi
240 iminium ion generated from alpha-(phenylthio)amidine precursor 16 by reaction with Cu(OTf)(2) undergo
241 conjugation of novel alpha,beta-unsaturated amidine precursors with proteins, methylarginine mimics
242 In the present study we investigated how Cl-amidine promotes survival, focusing on protective effect
244 ible region upon alteration of the amidinium/amidine protonation state; no such change is observed fo
245 yano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties
248 ycloaddition (C4/N1 vs C5/N2) as well as the amidine regioselectivity were unaffected by introduction
249 ve reaction pathway leading to an N-terminal amidine rendering the side chain thiol available for fur
251 at both the N-terminus and C-terminus of Cl-amidine result in >100-fold increases in PAD2 potency an
252 HCl to alkenylaldimines, -formamidines, and -amidines results in the protonation of the sp2-nitrogen
255 Copper-catalyzed cross-coupling reactions of amidine salts were utilized to synthesize monoarylated a
258 Because of the large dihedral, the reversed amidines should have reduced binding to DNA relative to
259 ion revealed a novel rearrangement affording amidines, specifically compound 45, which was found to p
262 was found to be modulated by the location of amidine substituents on the core phenyl-furan-phenyl rin
263 iplets, along with proper positioning of its amidine substituents to occupy the minor and the major-m
264 heterocyclic cations, a series of "reversed amidine" substituted heterocycles has been prepared.
266 ) catalyzes the ring opening of the bicyclic amidine system of DBU (1,8-diazabicyclo[5.4.0]undec-7-en
267 ly one amino-pyrrole-carboxamide unit and an amidine tail is connected to either side of a central di
269 benzimidazole-biphenyl system with terminal amidines that gives the compound a linear conformation w
270 benzimidazole-biphenyl system with terminal amidines that results in a linear conformation that does
271 of vancomycin aglycon residue 4 substituted amidines that were used to clarify their interaction wit
272 s from the arthritic mice treated with BB-Cl-amidine, there was a decrease in total cell numbers but
275 C3 deposition were significantly lower in Cl-amidine-treated mice compared with vehicle controls.
281 ymes mediating citrullination, through BB-Cl-amidine treatment, prevents diabetes development in NOD
284 The two most potent fragments exhibiting an amidine-type scaffold are not the most enthalpic binders
286 roach involves Ph3P-I2-mediated formation of amidine upon condensation of an amide or the intermediat
287 -haloenones with 1,3-dicarbonyl compounds or amidines utilizing K2CO3/DMSO at ambient temperature tha
288 The reaction proceeds by dual acylation of amidines via oxidative C(CO)-C(CO) bond cleavage of 1,2-
290 simple protocol, a diverse range of sulfonyl amidines was obtained in moderate to excellent yields.
291 d a highly functionalized and chiral primary amidine, which forms the pyrimidine cores and introduces
292 tion of the mechanism of NOS inactivation by amidines, which leads to heme degradation, also provides
293 de reaction of A(3)-coupling of heterocyclic amidine with aldehyde and alkyne, 5-exo-dig cycloisomeri
294 finity of compounds containing the residue 4 amidine with the model D-Ala-D-Ala ligand 2 was found to
295 -3-ones, available from cyclocondensation of amidines with dimethyl acetylenedicarboxylate (DMAD), un
297 D4 inactivation, the structure of the PAD4-F-amidine x calcium complex, and in vivo studies with N-al
298 he aforementioned dimer is assembled by dual amidine-Zn(II) coordination between neighboring Pc1 mole
299 and idazoxan produced monodiazeniumdiolated amidine zwitterions from which NO release was observed f