cas 2037-48-1, 2-DEOXYSTREPTAMINE, DIHYDROBROMIDE

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Novel Route to Functionalized Cyclooctanoids via [5+3] Cycloaddition
The self-dimerization of 3-oxidopyrylium leading to stereocontrolled formation of highly functionalized cyclo-octanoids is described. Different functionalities were introduced on the dimer (3) and the stereochemical outcome was determined by single-crysta
Krishna, Urlam Murali,Deodhar, Kodand D.,Trivedi, Girish K.,Mobin, Shaikh M.
p. 967 - 969
(2004)
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Neamine and 2-deoxystreptamine neomycin derivatives exhibit antinociceptive activity in rat models of phasic, incision and neuropathic pain
Objectives To assess the antinociceptive activity of the neomycin derivatives neamine and 2-deoxystreptamine following intraspinal administration in rats. Methods We used the tail-flick test and measured the threshold to mechanical stimulation in models of incisional and neuropathic pain. Key findings The derivatives produced antinociception in the tail-flick test and reduced mechanical allodynia in models of incisional and neuropathic pain. The approximate ED50 in milligrams (confidence limits in parenthesis) in these tests were 1.35 mg (0.61; 2.95), 0.20 mg (0.14; 0.27) and 0.28 mg (0.12; 0.63) for neamine, and 1.05 mg (0.68; 1.60), 0.78 mg (0.776; 0.783) and 0.79 mg (0.46; 1.34) for 2-deoxystreptamine, respectively. Neamine was more potent than 2-deoxystreptamine in the incisional and neuropathic pain models, but they had similar potency in the tail-flick test. Tetra-azidoneamine, a neamine derivative in which free amino groups are replaced with azido groups, did not change the incisional mechanical allodynia. The reduction of incisional allodynia by neamine and 2-deoxystreptamine was transitorily antagonized by intrathecal administration of calcium chloride. Conclusions The intraspinal administration of neamine and 2-deoxystreptamine is antinociceptive in rats. The presence of amino groups in the structure of these derivatives is fundamental to their antinociceptive effect, which may be due to a calcium antagonist activity.
Prado, Wiliam A.,Rossaneis, Ana C.,Carvalho, Ivone,Zamoner, Luis Otvio B.,Corrado, Alexandre P.
p. 1696 - 1704
(2015)
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Synthesis and biological evaluation of modified 2-deoxystreptamine dimers
Aminoglycosides are powerful antibiotics, but the emergence of resistant bacterial strains has prompted the search for analogues with better pharmacological profiles. The synthesis of 2-deoxystreptamine (2-DOS) dimers linked by polyamines and analogues based on furylcarbopeptoid skeletons is described. Potent and selective ligands for bacterial 16S rRNA were identified using microarray techniques by determining the affinity of these derivatives toward bacterial and human ribosomal RNAs. Georg Thieme Verlag Stuttgart - New York.
Coste, Gerald,Horlacher, Tim,Molina, Lidia,Moreno-Vargas, Antonio J.,Carmona, Ana T.,Robina, Inmaculada,Seeberger, Peter H.,Gerber-Lemaire, Sandrine
experimental part
p. 1759 - 1770
(2011/07/30)

miRNA PROCESSING INHIBITOR EFFICACY ASSAYS AND SUBSTANCES
The invention relates to assays for assessing miRNA maturation effector (preferably: inhibitor) efficacy, and to substances useful for influencing, particularly for inhibiting, maturation of miRNA. According to the invention there is provided assay of miR
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(2009/04/24)

Efficient preparation of a 1,3-diazidocyclitol as a versatile 2-deoxystreptamine precursor
A synthesis route toward 2-deoxystreptamine, a common structure in many of the clinically important aminoglycosides, is presented. Starting from p-benzoquinone and cyclopentadiene, 2-deoxystreptamine is synthesized with key steps involving Pd(0)-catalyzed
Busscher, Guuske F.,Groothuys, Stan,De Gelder, Rene,Rutjes, Floris P. J. T.,Van Delft, Floris L.
p. 4477 - 4481
(2007/10/03)

2-Deoxystreptamine derivatives, pharmaceutical compositions thereof and therapeutic methods using same
This invention provides a compound having the formula: STR1 wherein R1 and R3 independently are hydrogen, --CHO, --COCH3, --COR7, --A--Ar--(Q)z, etc.; wherein D is a C1-6 linear, C3-8 branched or cyclic group having from 4 to about 15 atoms, consisting of C, etc.; wherein D is unsubstituted or substituted with one or more groups independently selected from the group consisting of --OH, NH2, --NHR7, etc.; wherein each Q is independently --CNH(NHY), --NHCNH(NHY), --SO2 W, --SOW, etc.; wherein Y is hydrogen, alkyl, alkenyl, --B--NH2, --B--NHR8, etc.; wherein W is alkyl, alkenyl, --B--NH2, etc.; wherein A nd B independently are a bond, or a C1-6 linear, C3-8 branched or cyclic linking group having from 1 to about 15 atoms, consisting of C, optionally interrupted by N, S, P and O; wherein A and B independently are unsubstituted or substituted with --OH, NH2, etc.; wherein R7 is an alkyl, a branched alkyl, etc.; wherein R8, R9, and R10 are independently represented by hydrogen, alkyl, branched alkyl, etc.; wherein x is 0, 1 or 2; and z is 0, 1, 2, or 4; wherein R1 ' and R3 ' are independently selected from the group consisting of hydrogen, alkyl and benzyl, or alternatively, R1 and R1 ' or R3 and R3 ' with their respective nitrogen atoms independently form a phthalimido, succinimido, etc.; wherein R4, R5, and R6 independently are selected from the group consisting of hydrogen, --CHO, --COCH3, --COR7, etc.; therein said saccharides are optionally linked at the one position of said saccharid group; wherein R4 and R5, or R5 and R6, together comprise a methylidene, ethylidene, isopropylident, cyclohexylidene or benzylidene bridge, or R3 and R4, or R1 and R6, together independently form an intramolecular carbamate; wherein R5 is not hydrogen or glycosyl when R3 and R4, or R1 and R6, together independently form an intramolecular carbamate; with the provisio that at least two of R1, R1 ', R3, R3 ', R4, R5, and R6 are not hydrogen. Also provided are pharmaceutical compositions comprising the compound and methods of inhibiting binding of human immunodeficiency virus REV protein to RRE.
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(2008/06/13)

Asymmetric Synthesis of cis-1,3-Diamino-1,3-dideoxycyclitols
Starting with the hetero-Diels-Alder reaction of the O-isopropylidene-protected cis-cyclohexa-3,5-diene-1,2-diol with (-)-2,3:5,6-di-O-isopropylidene-1-nitroso-α-D-manno-furanosyl chloride the optically pure (+)-endo-adduct was exclusively formed.After re
Schuerrle, Karsten,Beier, Barbara,Piepersberg, Wolfgang
p. 2407 - 2412
(2007/10/02)

Enantiospecific syntheses of (+)-hyosamine and (-)-hyosamine
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Baer,Chen,Giziewicz
p. 1563 - 1574
(2007/10/02)

SYNTHESIS OF CARBOCYCLIC LIGNAN VARIANTS RELATED TO PODOPHYLLOTOXIN
Carbocyclic lignan variants related to podophyllotoxin were synthesized by a stereoselective BF3-catalyzed coupling of podophyllotoxin derivative with chiral aminocyclitols.
Saito, Hitoshi,Nishimura, Yoshio,Kondo, Shinichi,Takeuchi, Tomio
p. 1235 - 1238
(2007/10/02)

Aminoglycoside Antibiotics. 6. Chemical Reactions of Aminoglycosides with Disodium Carbenicillin
Aminoglycoside antibiotics including kanamycin A, tobramycin, and the gentamicin C complex reacted with 1 mol of disodium carbenicillin to give products derived from acylation of their amino groups by the β-lactam function of the carbenicillin.Amikacin wa
Iyengar, Bhashyam S.,Kumar, Virendra,Wunz, Timothy P.,Remers, William A.
p. 611 - 614
(2007/10/02)

Mechanism of the Formation of Two Epimeric Diamino-hexose Rings of Neomycin B
By using variously tritiated hexoses and Streptomyces fradiae (a neomycin-producer), the mechanism and stereochemistry of the formation of various subunits of neomycin B were investigated.The results of the incorporation of (6RS)-D-glucose into neomycin B followed by specific degradation showed that during the formation of the aminomethyl group of the neosamine B ring one of the 6-3H atoms of the precursor was removed.The 3H remaining at C-6 of the neosamine B ring was shown to be located in the HSi orientation through the isolation of the chiral centre as glycine and the analysis of the latter by using an exchange reaction catalysed by serine hydroxymethyltransferase.These results suggested that, as has been previously shown for neosamine C, the aminomethyl group of neosamine B is formed by an oxidation-transamination process;-CH2OH--> -CHO--> -CH2NH2.D-Glucose was prepared by an unambiguous method and incorporated into neomycin B.The radiochemical data on the various subunits of the antibiotic could be interpreted to suggest that the L-idose configuration at C-5 of the neosamine B ring is produced via an enolisation process involving a carbonyl group at either C-4 or C-6.The involvement of C-4 was then eliminated by feeding experiments in which it was shown that the hydrogen atom at C-4 of D-glucose was undisturbed during the incorporation of this position into the C-4 of neosamine B or C.
Goda, Sayed K.,Al-Feel, Walid,Akhtar, Muhammad
p. 1383 - 1390
(2007/10/02)

Polyfunctionalised Cyclohexanes from Dianhydrodeoxyinositols. cis-Deoxy-1,3(1,4)-inosadiamines from Benzene
A ca. 9 : 1 mixture (yield 87 - 90percent) of the stereoisomeric (1α,2α,6α)-/(1α,2β,6α)-2-bromo-7-oxa-bicyclohept-3-enes (7a/8a) is obtained via controlled NBS bromination of 4,5-epoxycyclohexene (5). 7a/8a are quantitatively equilibrated in the presence of tetraalkylammonium bromides (the equilibrium being controlled by the polarity of the solvent (3 : 7 in acetonitrile) and are isolated pure by chromatography.Through selective halogen substitution (7b/8b, 9b - d/10b - d) and ammonolysis the allylic epoxy alcohols 9a/10a are obtained in high yields.Stereospecific epoxidation of 7a/8a yields the (1α,2α,3α,5α,7α)-/(1α,2β,3α,5α,7α)-diepoxy bromides 12a/14a.The latter are equilibrated quantitatively to mixtures favoring either one in the ratio of ca. 9 : 1 (CCl4) and 1 : 9 (CH3CN), respectively.Upon SN2 substitution with ammonium acylates (-> 13b, c/15b, c) and ammonolysis the naturally not occurring dianhydrodeoxyinositols 13a/15a are isolated in practically quantitative yields.The usefulness of 13a/15a and of various derivatives for the stereoselective synthesis of cis-1,4- and cis-1,3-disubstituted cyclohexanetriols is exemplified by reactions with monovalent (H2O, HI, NaN3) and divalent nucleophiles (NH2NH2, CH3NHNH2).I.a. the cis-deoxy-1,3-inosadiamines 1 (2-deoxystreptamine)/2 and the cis-deoxy-1,4-inosadiamines 3/4 become available in high yields.
Kuehlmeyer, Rainer,Keller, Reinhold,Schwesinger, Reinhard,Netscher, Thomas,Fritz, Hans,Prinzbach, Horst
p. 1765 - 1800
(2007/10/02)

Di-and polyamino sugars. XXIX. Reactions of 2-deoxystreptamine with 5,6-anhydro sugars - synthesis of N-glycos-6-yl derivatives
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Spohr,Meyer zu Reckendorf
p. 821 - 829
(2007/10/02)

Semisynthetic Aminoglycoside Antibacterials. Part 9. Synthesis of Novel 1- and 3-Substituted and 1- and 3-epi-Substituted Derivatives of Sisomicin and Gentamicin from the 1- and 3-Oxo-derivatives
The conversion of selectively protected gentamicin and sisomicin derivatives into the 1- and 3-oxo-compounds by reaction with 3,5-di-t-butyl-1,2-benzoquinone is described.By application of suitable reductive techniques these oxo-aminoglucosides have been converted into novel 1- and 3-epi-, 1- and 3-deamino-1- and -3-hydroxy-, 1- and 3-deamino-1- and -3-epi-hydroxy, and 1-deamino-derivatives.A study of the 13C n.m.r. parameters of the 1-epi- and 1-deamino-derivatives has led to the assignment of novel solution conformations for these new aminoglycosides.
Boxler, Dena L.,Brambilla, Raymond,Davies, D. Huw,Mallams, Alan K.,McCombie, Stuart W.,at al.
p. 2168 - 2185
(2007/10/02)

Aminoglycoside antibiotics. VI. Structure determination of 4' deoxybutirosins (BU 1975C1 and C2)
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Konishi,Numata,Shimoda,Tsukiura,Kawaguchi
p. 471 - 483
(2007/10/05)