Solid-phase synthesis of substituted benzimidazoles

Tumelty, David; Schwarz, Matthias; Cao, Kathy; Needels, Michael C.

doi:10.1016/s0040-4039(99)01299-x

Cited by 45 publications

(18 citation statements)

References 7 publications

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“…An important number of solid-phase synthesis of benzimidazoles has been reported and in most cases ofluoronitrobenzene derivatives attached to a polymer are used as the starting material [25][26][27][28][29][30][31][32]. This approach does not allow much substituent diversity on the benzene ring.…”

Section: 1-imidazole and Imidazole N-oxidementioning

confidence: 99%

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Imidazole and Benzimidazole Derivatives as Chemotherapeutic Agents

Boiani¹,

González

2005

MRMC

420

198

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Imidazole and benzimidazole systems are presented in a large number of common therapeutics agents. They were widely used in organic and medicinal chemistry, but recently the development of N-oxide derivatives got an improvement from the point of view of its chemical and biological activity. Though we will review recent developments in chemical and biological profiles (as antitumoral, antiparasitic, antiviral and antimicrobial agents) of these heterocycle systems and the corresponding N-oxides.

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Section: 1-imidazole and Imidazole N-oxidementioning

confidence: 99%

“…An important group of 1H-benzimidazoles are 2-carbamates-benzimidazole derivatives, which posses antihelmintic activity, such as Albendazole (26) and Mebendazole (27) employed in clinic for the 70 decades (Fig. (13)).…”

Section: H-benzimidazolementioning

confidence: 99%

Imidazole and Benzimidazole Derivatives as Chemotherapeutic Agents

Boiani¹,

González

2005

MRMC

420

198

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“…2 As a part of our project to develop efficient synthetic methods for heterocyles, 3 we have investigated the solid-phase synthesis of 2,1,3-benzothiadiazin-4-one 2-oxides as they are similar to other important heterocycles such as quinazoline-2,4-diones, 3d,4 2-thioxoquinazolin-4-ones, 3a,3c 4-quinazolinones, 3b,5 1,2,4-benzothiadiazine 1,1-dioxide, 3e 1,2,4-benzothiadiazin-3-one 1,1-dioxide, 3f benzimidazole, 6 hydantoin, 7 2-piperazinone 8 Since these heterocycles have been prepared from solid-supported primary amines including nitrogen atoms as parts of the heterocycles, they can easily be compared to bioactivities of 2,1,3-benzothiadiazin-4-one 2-oxides by developing the appropriate solid-phase chemistry ( Figure 1). Nevertheless, to the best of our knowledge, there has been only one report of the synthesis of 2,1,3-benzothiadiazin-4-one 2-oxides in solutionphase.…”

mentioning

confidence: 79%

Efficient Solid-phase Synthesis of 2,1,3-Benzothiadiazin-4-one 2-Oxides with SynPhase™ Lanterns

Makino¹,

Nakanishi²,

Tsuji³

2003

Bulletin of the Korean Chemical Society

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“…The compounds were prepared manually on solid phase using the para-MBHA resin (Matsueda and Stewart, 1981) following reported procedures (Smith et al, 1999;Tumelty et al, 1999) with modifications (Fig. 1).…”

Section: Drug Synthesismentioning

confidence: 99%

Histogranin-Like Antinociceptive and Anti-Inflammatory Derivatives ofo-Phenylenediamine and Benzimidazole

Le¹,

Lemaire²,

Gilbert³

et al. 2004

J Pharmacol Exp Ther

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Histogranin (HN)-like nonpeptides were designed and synthesized using benzimidazole (compound 1) and o-phenylenediamine (compounds 2-7) as scaffolds for the attachment of phenolic hydroxyl and basic guanidino pharmacophoric elements present in HN. The benzimidazole derivative N-5- (2) were more potent analgesics than HN in both the mouse writhing (5.5 and 3.5 as potent as HN, respectively) and tail-flick (11.8 and 8.0 as potent as HN, respectively) pain assays. Improvements in the potencies and times of action of compound 2 in the mouse writhing test were obtained by attaching carboxyl (6) or p-Cl-benzoyl (7) groups at position 4 of the (2R) o-phenylenediamine derivative (5). In rats, compounds 2 (80 nmol i.t.), 6 (36 nmol i.t.), and 7 (18 nmol i.t.) were effective in blocking both persistent inflammatory pain in the formalin test and hyperalgesia in the complete Freund adjuvant assay. Compounds 2, 6, and 7, but not compound 1 at 10 nmol (i.c.v.) also mimicked the HN (60 nmol i.c.v.) blockade of N-methyl-D-aspartate (NMDA)-induced convulsions in mice. Finally, in primary cultures of rat alveolar macrophages, HN and compounds 1, 2, 6, and 7 (10 Ϫ8 M) significantly blocked lipopolysaccharide-induced cyclooxygenase-2 induction and prostaglandin E 2 secretion. These studies indicate that both derivatives of benzimidazole and o-phenylenediamine mimic the in vivo antinociceptive and in vitro anti-inflammatory effects of HN, but the HN protection of mice against NMDA-induced convulsions is mimicked only by the o-phenylenediamine derivatives.

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Solid-phase synthesis of substituted benzimidazoles

Cited by 45 publications

References 7 publications

Imidazole and Benzimidazole Derivatives as Chemotherapeutic Agents

Imidazole and Benzimidazole Derivatives as Chemotherapeutic Agents

Efficient Solid-phase Synthesis of 2,1,3-Benzothiadiazin-4-one 2-Oxides with SynPhase™ Lanterns

Histogranin-Like Antinociceptive and Anti-Inflammatory Derivatives ofo-Phenylenediamine and Benzimidazole

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