Indoloparacyclophanes: Synthesis and Dopamine Receptor Binding of a Novel Arylbioisostere

Abstract

Fancy drug candidates: The first preparation of indoloparacyclophanes is reported through the use of the Buchwald variant of the Fischer indole synthesis (see scheme). Receptor binding studies clearly demonstrated that the double‐layered molecular scaffold can serve as an effective arylbioisostere.

DMAP‐[2.2]paracyclophane: Observation of an Unusual C–C Insertion

“…The anionic part of this zwitterion then attacks the proximate CH 2 position, which is thought to be unusually electrophilic due to its location β to the C-4 carbocation. Similar reactivity involving carbon atoms in the benzylic position acting as an electrophile has been reported by Gmeiner [16] in the course of a Fischer-Indole synthesis. From the X-ray diffraction diagram of 8, one can note the drastic distortion imposed upon the quinolone moiety by the cyclophanic scaffold, indicating that such a compound is far from lying in an energetic minimum.…”

“…For preparative purposes, the mixture was used without purification in the next step. 3 Hz, 1 H, 12-H), 6.44 and 6.33 (2 ϫ dd AB system, J = 2.1, 7.9 Hz, 2 H, 19-H, 20-H), 6.19 and 6.06 (2 ϫ dd AB system, J = 1.9, 7.7 Hz, 2 H, 16…”

Antibacterial and antioxidant activities for natural and synthetic dual-active compounds

“…It is well known that the indole moiety is a bioactive nucleus present in diverse natural products [155,156]. Even if indole-based cyclophanes are not so frequently reported [157], these systems are encountering attention during recent times due to their biological applications. Furthermore, N-arylindoles represent an important class of pharmacophores with a wide variety of bioactivities, such as antiestrogenic, analgesic, antiallergy, cyclooxygenase (COX)-1 inhibitory, and anti-HIV-1 activity [158e162].…”