1994
DOI: 10.1021/jm00051a010
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DNA-Directed Alkylating Agents. 6. Synthesis and Antitumor Activity of DNA Minor Groove-Targeted Aniline Mustard Analogs of Pibenzimol (Hoechst 33258)

Abstract: A series of nitrogen mustard analogues of the DNA minor groove binding fluorophore pibenzimol (Hoechst 33258) have been synthesized and evaluated for antitumor activity. Conventional construction of the bisbenzimidazole ring system from the piperazinyl terminus, via two consecutive Pinner-type reactions, gave low yields of products contaminated with the 2-methyl analogue which proved difficult to separate. An alternative synthesis was developed, involving construction of the bisbenzimidazole from the mustard t… Show more

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Cited by 143 publications
(67 citation statements)
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“…General. 1 H NMR spectra were recorded on a Bruker 300-MHz spectrometer in the solvent indicated with TMS as the internal standard. All chemical shifts are given in ppm and the coupling constants are given in Hz.…”
Section: Biological Results and Discussionmentioning
confidence: 99%
See 1 more Smart Citation
“…General. 1 H NMR spectra were recorded on a Bruker 300-MHz spectrometer in the solvent indicated with TMS as the internal standard. All chemical shifts are given in ppm and the coupling constants are given in Hz.…”
Section: Biological Results and Discussionmentioning
confidence: 99%
“…Compounds that exhibit the functionality of benzimidazoles have been used in the area of pharmaceuticals [1][2][3][4][5] . These high profile applications of compounds with benzimidazoles structures have prompted extensive studies for their synthesis.…”
Section: Introductionmentioning
confidence: 99%
“…Benzimidazole derivatives are very useful intermediates of pharmaceutically important compounds [8]. They are applicable as antiulcer, antihypertensive, antifungal, antiviral, antihistamine, antimicrobial, antiallergic, antioxidant, antitubercular, and in-vitro anti-HIV-1 [9].…”
Section: Introductionmentioning
confidence: 99%
“…Substituted benzimidazole derivatives have found applications in diverse therapeutic areas including antihypertensives, antivirals, antifungals, anticancers, and antihistaminics [1]. There are two general methods for the synthesis of 2-substituted benzimidazole.…”
Section: Introductionmentioning
confidence: 99%