Benzimidazol‐Derivate und verwandte Heterocyclen III. Synthese von 1‐Aminoalkyl‐2‐nenzyl‐nitro‐benzimidazolen

Abstract

The synthesis of a series of 1‐aminoalkyl‐2‐benzyl‐nitro‐benzimidazoles is described. Many of the 5‐nitro‐benzimidazoles prepared show strong analgesic activity. 1‐(β‐Diethylamino‐ethyl)‐2‐(p‐ethoxy‐benzyl)‐5‐nitro‐benzimidazole (XXXVIII) is 1000 times as potent as morphine and therefore the most active analgesic known until now.

Report on a novel emerging class of highly potent benzimidazole NPS opioids: Chemical and in vitro functional characterization of isotonitazene

“…The obtained data revealed that isotonitazene has a high potency (EC 50 of 11.1 nM) and efficacy (E max 180% of that of the reference compound used in this assay, hydromorphone), indicating that this compound is a strong opioid (which is also in good correspondence with data previously reported in the literature 16,34,35 ). These values are even slightly higher than those we obtained for the known potent E max = 155% (95%CI: 149-161), unpublished results).…”

“…We therefore hypothesized that the obtained powder sample was a salt, most likely of inorganic origin, given the lack of additional signals in the 1 H and 13 C spectrum. A melting point determination gave a mp of 174 C, indicating that the obtained compound is a HCl salt, as this is in line with the reported mp of 172-173 C. 35 From all the above-mentioned analyses, we concluded that the powder sample that was obtained online is of high purity.…”

“…Chemically, the nitro‐group at the 5‐position of the benzimidazole ring appears to be optimal for high analgesic activity. For etonitazene, the removal of this nitro group (des‐nitro analog) or repositioning of this nitro group to the 6‐position was reported to result in a reduction of antinociceptive activity, although the resulting compounds were respectively still 70‐ and 20‐fold more potent than morphine in vivo . Since multiple substances in the benzimidazole class trump morphine's potency by at least an order of magnitude, the number of future possible benzimidazole opioids cannot be underestimated.…”

Product Class 4: Benzimidazoles

“…Scheme 10 Reaction of 1,2-Diaminoarenes with Imidates [105,114,115,118,492] [118] H Cl H MeOH 55 [118] H Cl Cl MeOH 67 [118] H Me H DME 60 [118] Me H H MeOH 90 [118] Ethyl 2,4-Dinitrophenylacetimidate Hydrochloride: [114] To 2,4-dinitrophenylacetonitrile (20.7 g, 0.10 mol) in dry CHCl 3 (200 mL) was added EtOH (6 mL). The soln was cooled to 0 8C and then saturated with dry HCl during 0.5 h. After standing for 12 h at 0 8C, the colorless crystalline product was filtered and washed with dry CHCl 3 ; yield: 25 g (86%); mp 181 8C.…”

1, 5, 4' -Trisübstitüe-2-benzilbenzimidazol Türevleri Üzerinde Yapı-Etki İlişkisi Yönünden Araştırmalar-I. Bazı 5, 4'-Disübstitüe- 2-benzilbenzimidazol Türevlerinin Sentez, Yapı Açıklamaları ve Mikrob

“…1,4,5'-Trisübstitüe-2-Benzilbenzimidazol Türevleri. 5 Antibakteriyel aktiviteleri incelenecek olan bileşiklerin alkoldeki steril çözeltilerinden, her bakteri için hazırlanmış serinin ilk tüpüne 400 g/ml ) olacak şekilde ilave edilip, tüpten tüpe aktarılımlarla 10 dilusyon (400, 200, 100, 50, 25, 12,5, 6.2, 3.1, 1.5, 0. 7 g/ml) hazır-zırlandı.…”