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1 ance stabilized iminoquinone (i.e., extended amidine).
2 cyclization to form the corresponding cyclic amidine.
3 f the second generation PAD inhibitor, BB-Cl-amidine.
4 ylamide are good alternatives for the second amidine.
5 sosteres for the parent pan PAD inhibitor Cl-amidine.
6 hesize 1,3,5-trizines from acetophenones and amidines.
7 ore the remarkable behavior of the residue 4 amidines.
8 pre-organized for a fit to the heterocyclic amidines.
9 e reduced binding to DNA relative to similar amidines.
10 ial relationship with the groove relative to amidines.
11 azoles in the preparation of polysubstituted amidines.
12 azole-biphenyl isomers with terminal charged amidines.
13 amidine substituents and DB226 has 3-pentyl amidines.
14 d sulfonamide enables efficient synthesis of amidines.
15 oduce five-, six-, and seven-membered cyclic amidines.
16 robic [3+2]-annulation reaction of N-alkenyl amidines.
17 ute toxicity usually exhibited by the parent amidine 1 at a dosage level of 22 micromol/kg/day on int
27 ifluoromethyl-4-iodo-nicotinic acid (2) with amidine 9a catalyzed by Pd(2)(dba)(3) and Xantphos, foll
29 2-chloro-1-iminoethyl)-L-ornithine amide (Cl-amidine), a recently described pan-PAD inhibitor, could
32 rted the synthesis and characterization of F-amidine, a potent and bioavailable irreversible inactiva
34 transformation of the 5-cyano group into an amidine allows synthesis of 2,5-terpyrimidinylenes with
35 potent PAD4 inhibitors, we show here that Cl-amidine also exhibits a strong inhibitory effect against
39 f mechanistic studies of NOS inactivation by amidine analogues of l-arginine and other previous mecha
41 nces arise from specific interactions of the amidine and amine groups with the active-site residues o
42 We confirmed survival-improving effect of Cl-amidine and are the first to explore the role of Cl-amid
43 investigation of the activity of a series of amidine and bisamidine compounds against Staphylococcus
44 ir assessment indicates that combined pocket amidine and CBP peripherally modified analogues exhibit
45 novel and diverse compounds based on cyclic amidine and guanidine cores were synthesized with the go
49 zed oxidative cyclization of 2-aminopyridine/amidine and isothiocyanate via N-S bond formation at amb
50 ICs = 0.06-0.005 and 0.5-0.06 mug/mL for the amidine and methylene analogues, respectively) and likel
51 phase behavior and microstructure of diC(14)-amidine and of the lipid/DNA (circular plasmid, 5.4 kb)
53 cin stems from its unprecedented macrocyclic amidine and rare beta-methylated amino acid residues.
56 m exchanges in the binding pocket (residue 4 amidine and thioamide) are disclosed as well as their pe
62 to the formation of the corresponding cyclic amidines and guanidines, typically in good to excellent
63 he first time the development of phosphonate amidines and sulfonate amidines as isosteres of pArg and
65 emonstrated by 33 examples with a variety of amidines and three different 4H-pyrido[1,3]oxazin-4-one
68 ion with substituents between the vinylogous amidine, and hydrolytic properties that can be controlle
69 mall molecules and macromolecules containing amidine, and to a lesser extent, guanidine functional gr
70 vided by a benzimidazole (or indole) -NH and amidines, and (iii) appropriate curvature of the dimer c
73 r of potency in the series was: guanidines > amidines approximately quaternary ammonium > amines.
74 al proteins observed in mice treated with Cl-amidine are consistent with the notion that Cl-amidine d
75 to an aromatic ring and a sterically compact amidine are key pharmacophores for this class of NOS inh
81 opment of phosphonate amidines and sulfonate amidines as isosteres of pArg and then use these mimics
84 oxylation step during inactivation of NOS by amidines as well as the HO-catalyzed reaction, the essen
85 interaction of a key compound, which has the amidine at the phenyl shifted from the para position in
86 itively charged group such as an amine or an amidine at this position results in improved affinity fo
87 ensation of 4H-pyrido[1,3]oxazin-4-ones with amidines at room temperature or under microwave irradiat
88 rom PFAA-enamine cycloadditions rearrange to amidines at room temperature, while (3 + 2) cycloadditio
90 col substituted phthalocyanines utilizing an amidine-base-promoted phthalonitrile tetramerization rea
94 to the discovery of a novel series of cyclic amidine-based inhibitors of beta-secretase (BACE-1).
100 oroaryl ring, and a phenyl ring linked by an amidine bond, were efficiently synthesized by a straight
101 conformer relative to rotation about the P-C(amidine)() bond; however, DFT calculations indicate a lo
102 containing natural products are converted to amidines by a C-H amination-oxidation sequence or to hyd
103 constitutes a bioorthogonal approach toward amidines by avoiding the use of amines and transition-me
104 o radius of curvature from amidine carbon to amidine carbon but a significant dihedral twist across t
105 ives for targeting the minor groove have the amidine carbon linked to a central heterocyclic system,
106 mpounds have a zero radius of curvature from amidine carbon to amidine carbon but a significant dihed
107 bstrate by hydrogen atom abstraction from an amidine carbon, the 5'-deoxyadenosyl radical abstracts h
111 orin associated to NI are consistent with an amidine-carboxylic acid interface, which is also verifie
113 oton to the carboxylate to form a nonionized amidine-carboxylic acid two-point hydrogen network, wher
115 ne) (14), has been reported to give a cyclic amidine complex when treated with 2 equiv of 2,6-dimethy
116 compounds, biphenyl tetrazole tert-butyl Cl-amidine (compound 13), exhibits enhanced cell killing in
121 ly observed for iNOS inactivation by another amidine-containing compound, N5-(1-iminoethyl)-L-ornithi
124 d on the basis of the N'-(4-halopyrazol-5-yl)amidine cyclization under the conditions of copper-catal
127 or the preparation of alpha,beta-unsaturated amidine derivatives appears to offer high yield, mild co
128 ken together, the data indicate that several amidine derivatives display functional selectivity for m
131 mechanisms of decomposition of guanidine and amidine derivatives in aqueous solution and the rate enh
132 ic guanidine, N-alkylguanidine, and reversed amidine derivatives of fused ring systems have been synt
133 d provides authentic residue 4 thioamide and amidine derivatives of the vancomycin aglycon that will
135 idine are consistent with the notion that Cl-amidine derives its efficacy from its ability to inhibit
139 ional bonding overlaps in the HOMO, and this amidine effect predicts lower N-inversion barriers in an
140 l-N'-tetradecylamino-propionamidine (diC(14)-amidine), efficiently ports DNA into mammalian cells in
142 h possesses the ethylene tether and extended amidine feature found in the pyrroloiminoquinone natural
143 we show the versatility of these vinylogous amidines for organic synthesis, including the following:
145 yield, presumably via novel Sn (IV)-mediated amidine formation from the initial aniline reduction pro
147 ary carboxamides exhibit different outcomes, amidine formation versus transamidation, depending on th
149 cules exist as zwitterions with a protonated amidine fragment of the eight-membered ring neutralizing
150 diamine tautomer of a variety of substituted amidine free bases reacts with nitric oxide (NO) to prod
151 at the active site prevent the inhibitor S1 amidine from forming direct hydrogen bonds with Asp189 b
152 ecarboxylation cascade synthesis of sulfonyl amidines from sulfonyl azides and substituted amides at
153 elationships determined that, apart from the amidine function, an indole or benzimidazole and an orth
154 ystal, a solution of inhibitor containing an amidine functional group on a naphthalene ring was added
157 lation, which liberates the desired sulfonyl amidines, generating N2 and CO2 as the only reaction byp
158 ion of a hydroxyl group para to the proximal amidine group increases the potency vs fXa by 1-2 orders
160 te that substitution of the thiourea with an amidine group leads to greatly enhanced cytotoxicity in
161 Certain exogenous nucleobases that share the amidine group of adenine restored activity to abasic rib
162 ural and biochemical evidence implicated the amidine group of an active site adenosine, A38, in a pH-
164 f either carboxylic acid ligands through the amidine group or pyridine-type ligands through the Zn(II
165 interaction and a replacement for the distal amidine group that binds in the S3/S4 pocket of fXa.
168 terminal phenyl substituent on the reversed amidine groups as critical components in the strong bind
169 he new synthetic compounds have two aromatic-amidine groups for A/T recognition, and these are connec
172 ements indicate that the position of the two amidine groups on the carbazole ring influences signific
175 have demonstrated the importance of the two amidine groups, the cycloheptanone ring, and the (Z,Z) o
177 This tutorial review highlights the use of amidine, guanidine, and related isothiourea catalysts in
178 wis pair catalysts composed of a Lewis base (amidine, guanidine, or quaternary onium salts) and a Lew
179 l review is largely organized by the type of amidine/guanidine and transition metal used and covers l
181 ll nitrogen bases: nitriles, azoles, azines, amidines, guanidines, vinamidines, biguanides, and phosp
184 ns, but the linking group for the two phenyl amidines has a pK(a) of 6.3 that is susceptible to a pro
185 ethod for the synthesis of bi- and tricyclic amidines has been developed through copper-catalyzed aer
186 ne-pot domino reaction of 1,2-diketones with amidines has been identified that enables their transfor
187 ies of benzimidazole-based derivatives of Cl-amidine, hypothesizing that this scaffold would allow ac
188 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
207 (2) abstraction of a hydrogen atom from the amidine methyl group followed by attachment to the heme
208 oes substrate L-arginine, but because of the amidine methyl group, the heme peroxy intermediate canno
209 etween the electronegative tip and guanidine-amidine moiety extends the conjugation and facilitates n
210 mical and structural analyses pinpointed the amidine moiety of base Ade38 as a key functional group i
211 the introduction of fluorine adjacent to the amidine moiety, resulting in in vivo brain reduction of
213 g at different sites of a (Zn)phthalocyanine-amidine molecule (Pc1), enables the dissociation of the
214 rd the Ala190 enzymes is observed due to the amidine N1 nitrogen of the bound inhibitor being deprive
217 val of a single methylene bridge between the amidine nitrogen and phenyl ring to give N-(3-(aminometh
220 involved water-mediated H-bonds between one amidine of the compound and DNA bases at the floor of th
221 stal structure of the complex shows that the amidine of ZK-807834 forms a salt bridge with Asp189 in
222 ran that, when amplified out to the terminal amidines of the benzimidazole compounds, yields a very s
225 cooperative dimer to form but removal of one amidine or addition of an alkyl group to the amidine str
226 It was also demonstrated that the required amidine or iminocarbamate directing group fulfills two m
227 cribed here was the discovery of a novel bis(amidine) organocatalyst that provides high enantioselect
229 mpared with 2-PAM, the most promising cyclic amidine-oxime (i.e., 12e) showed comparable or greater r
234 t (i.e., 5 min after OP exposure, i.p,) with amidine oximes 7a-c and 12a, 12c, 12e, 12f, and 15b (145
237 istry of nine acyclic secondary and tertiary amidines (Ph-N=C(R(1))NR(2)R(3); R(1) = H, CH(3), Ph; R(
238 nd that an aromatic dication, DB293, with an amidine-phenyl-furan-benzimidazole-amidine structure can
239 be lead optimization focused on reducing the amidine pKa while optimizing interactions in the BACE1 a
240 The nitro- or cyano-substituted guanidine/amidine planes of the neonicotinoids provide a unique el
241 Collectively, our results demonstrate Cl-amidine plays protective roles by significantly decreasi
242 iminium ion generated from alpha-(phenylthio)amidine precursor 16 by reaction with Cu(OTf)(2) undergo
243 conjugation of novel alpha,beta-unsaturated amidine precursors with proteins, methylarginine mimics
244 In the present study we investigated how Cl-amidine promotes survival, focusing on protective effect
246 ible region upon alteration of the amidinium/amidine protonation state; no such change is observed fo
247 yano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties
250 ycloaddition (C4/N1 vs C5/N2) as well as the amidine regioselectivity were unaffected by introduction
252 at both the N-terminus and C-terminus of Cl-amidine result in >100-fold increases in PAD2 potency an
253 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
260 ded water network in the minor groove at one amidine site, which alters the orientation of the isopro
261 ion revealed a novel rearrangement affording amidines, specifically compound 45, which was found to p
264 , with an amidine-phenyl-furan-benzimidazole-amidine structure can recognize specific sequences of DN
265 ne-derived inhibitors of factor Xa (fXa), an amidine substituent was incorporated on one of the benzo
266 ine substituents while DB244 has cyclopentyl amidine substituents and DB226 has 3-pentyl amidines.
267 was found to be modulated by the location of amidine substituents on the core phenyl-furan-phenyl rin
268 iplets, along with proper positioning of its amidine substituents to occupy the minor and the major-m
269 parent compound, furamidine (DB75), has two amidine substituents while DB244 has cyclopentyl amidine
270 heterocyclic cations, a series of "reversed amidine" substituted heterocycles has been prepared.
272 ly one amino-pyrrole-carboxamide unit and an amidine tail is connected to either side of a central di
274 benzimidazole-biphenyl system with terminal amidines that gives the compound a linear conformation w
275 benzimidazole-biphenyl system with terminal amidines that results in a linear conformation that does
276 of vancomycin aglycon residue 4 substituted amidines that were used to clarify their interaction wit
277 s from the arthritic mice treated with BB-Cl-amidine, there was a decrease in total cell numbers but
280 C3 deposition were significantly lower in Cl-amidine-treated mice compared with vehicle controls.
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 e been introduced at the 5 position: amides, amidines, ureas, guanidines, amines, heterocycles, heter
288 -haloenones with 1,3-dicarbonyl compounds or amidines utilizing K2CO3/DMSO at ambient temperature tha
289 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
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