ChemInform Abstract: DEHYDRATION OF 2‐NITRO‐3‐HYDROXY‐4‐METHYLBENZOIC ACID

Glibin, E. N.; Tsukerman, B. V.; Tsymbalova, S. S.; Ginzburg, O. F.

doi:10.1002/chin.197723233

Cited by 2 publications

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“…ole-imidazole dipeptides 5-7 were virtually inactive (ID^, = »200 Mg/mL), whereas the triimidazole derivatives 8 showed a moderate inhibitory effect on tumor cell proliferation (ID50 = 42-100 Mg/mL). The (triethylamino)and (trimethylamino)-acetyl derivatives of netropsin (9, 10a, the latter bearing an amide group instead of the usual amidine) showed equal or lesser cytostatic activity than netropsin itself (11) whereass 10 had virtually no cytostatic activity.…”

Section: Resultsmentioning

confidence: 99%

Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin

Jw¹,

Krowicki²,

Balzarini³

et al. 1986

J. Med. Chem.

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A group of oligopeptides have been synthesized that are structurally related to the natural antiviral antitumor agents netropsin and distamycin. Cytostatic activity against both human and murine tumor cell lines as well as their in vitro activity against a range of viruses is reported. The biological activity of these agents is discussed both in terms of their structural differences and, in particular, in relation to their observed base- and sequence-dependent minor-groove binding to duplex oligonucleotides.

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Section: Resultsmentioning

confidence: 99%

Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin

Jw¹,

Krowicki²,

Balzarini³

et al. 1986

J. Med. Chem.

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“…Distamycin A (1), a naturally occurring substance isolated from Streptomyces distallicus,1 has been the subject of numerous chemical1"6 and biological investigations.7,8 It has antiviral, antitumor, and antibacterial activity and forms complexes with various types of DNA, thus inhibiting DNA-dependent syntheses. 7 It is a member of a modest class of oligopeptides, all of which are biologically active; this class includes anthelvencin A (2),9 congocidin (3),10 and kikumycin B (4),11 which contain a common pyrrole subunit, and amidinomycin (5) 12 and noformycin (6),13 which are nonaromatic. Their biological activity has stimulated much work in several fields, including molecular biological endeavors, since the interactions of distamycin A and congocidin with DNA reveal substantial information about the DNA.…”

mentioning

confidence: 99%

Permethyl analog of the pyrrolic antibiotic distamycin A

Gendler¹,

Rapoport²

1981

J. Med. Chem.

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The synthesis of an analogue of distamycin A, a pyrrolic oligopeptide possessing antiviral and antibiotic activity, is described in which each of the three pyrrole rings is fully methylated. This structural modification results in pyrrole rings which are extraordinarily electron rich and required the development of a new synthetic approach to these polypyrrolic amides. The key reactions involved development of a general method for the synthesis of 3-aminopyrroles and for formation of an amide bond between a pyrrole-2-carboxylic acid and these 3-aminopyrroles. Since the acid is hindered, a poor electrophile, and acid sensitive, while the amine is unstable and a hindered, weak nucleophile, amide bond formation under the usual conditions was poor. A very efficient method, however, was developed involving the isolation of 1-hydroxybenzotriazole active ester prepared in situ from another active ester. Neither the mono-, di-, nor tripyrrolic permethyl analogues were effective antimalarials, and none showed anticancer activity.

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ChemInform Abstract: DEHYDRATION OF 2‐NITRO‐3‐HYDROXY‐4‐METHYLBENZOIC ACID

Cited by 2 publications

References 0 publications

Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin

Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin

Permethyl analog of the pyrrolic antibiotic distamycin A

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