Synthesis of a 7-(aminomethyl)indole and related bis-indole derivatives

A 7-(aminomethyl) indole is a useful precursor to form a new range of unsymmetrical and symmetrical 3-substituted amide-, imine-, and amine-linked 7,7'-bis-indoles. The reduction of an imine linked bis-indole leads to formation of the corresponding amine-linked bis-indole.University of New South Wales; Turkish GovernmentTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK)We thank the University of New South Wales and the Turkish Government for their financial support

2-Bromo-5,7-dimeth­oxy-4-phenyl­quinoline

The title compound, C17H14BrNO2, was synthesized by the treatment of 5,7-dimeth­oxy-4-phenyl­quinolin-2-one with phosphoryl bromide in a Vilsmeier-type reaction. There are two independent mol­ecules (A and B) in the asymmetric unit which differ by 11.2° in the orientation of the 4-phenyl ring with respect to the planar quinoline ring system [dihedral angles = 55.15 (8) and 66.34 (8)° in mol­ecules A and B, respectively]. In the crystal structure, the independent mol­ecules are linked via C—H⋯N and C—H⋯O hydrogen bonds, forming centrosymmetric tetra­meric units which are cross-linked through C—H⋯π and C—Br⋯π inter­actions with Br⋯centroid distances of 3.4289 (8) and 3.5967 (8) Å

Short Cationic Peptidomimetic Antimicrobials

The rapid growth of antimicrobial resistance against several frontline antibiotics has encouraged scientists worldwide to develop new alternatives with unique mechanisms of action. Antimicrobial peptides (AMPs) have attracted considerable interest due to their rapid killing and broad-spectrum activity. Peptidomimetics overcome some of the obstacles of AMPs such as high cost of synthesis, short half-life in vivo due to their susceptibility to proteolytic degradation, and issues with toxicity. This review will examine the development of short cationic peptidomimetics as antimicrobials

Synthesis of Imine and Amine-Linked Macrocycles Containing Tris-Indoles

The synthesis of 21-membered imine-and amine-linked tris-indole macrocycles starting from 7-nitroethylindoles is described. The 7-nitroethylindoles are converted to 2,2'-diindolylmethanes and the nitro groups reduced to amino. The resulting diamines undergo reactions with indole-2,7-dicarbaldehydes to form the macrocyclic imines, which can subsequently be reduced to the macrocyclic amines.University of New South Wales; Turkish GovernmentTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK)The authors thank the University of New South Wales and the Turkish Government for their financial support

Some electrophilic reactivity studies of di-(2-indolyl)dibenzofurans and di-(2-indolyl)carbazoles

3,6-Bis-(2-indolyl)dibenzofurans 1,2, and carbazoles 3-6 underwent a range of electrophilic substitution reactions to produce formyl indoles 7-12, biindolyls 24-28 and 33-34, glyoxylamides 40-42, and amides 48. (C) 2014 Elsevier Ltd. All rights reserved.University of New South Wales; Turkish GovernmentTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK)We thank the University of New South Wales and the Turkish Government for their financial support

Synthesis, Reactivity and Biological Properties of Methoxy-Activated Indoles

Indoles continue to play a central role in the development of new structures of chemical and biological interest. They are the source of numerous biologically active natural products by virtue of their derivation from tryptophan units which are essential to peptide, protein and enzyme structures. Although the indole unit is electron rich and displays a wide range of reactivity, many naturally-occurring indoles contain methoxy substituents, which enhance their reactivity. The synthesis of methoxyindoles has also become a strategy for diversifying the regiochemical behaviour of indoles. This review brings together a wide range of information relating to indoles incorporating one, two, or three methoxy groups. It deals with aspects of synthesis, reactivity, and biological activity as well as summarizing the scope of important natural products © 2021, Targets in Heterocyclic Systems.All Rights Reserved.University of New South Wales, UNSWWe thank the University of New South Wales and the Turkish Government for financial support

Substituent effects in solid-state assembly of activated benzotriazoles

Aromatic donor-acceptor stacking involving electron-rich -donors and electron-deficient -acceptors has been utilized in a broad spectrum of diverse applications to great effect. We report the discovery of unprecedented donor-acceptor stacking from a non-mixed activated benzotriazole scaffold to give cofacial -stacking in 2D sheets. We further report the effects of altering the substituents of the bicyclic aromatic system. It was found that any alteration made to the substituents disrupted the cofacial stacking, however, both aromatic donor-acceptor stacking and 2D sheet formation was observed in the solid-state assembly of the analogues. Furthermore, interactions that satisfied both electrostatic and direct-substituent -stacking models were observed.National Health and Medical Research Council (NHMRC) AustraliaNational Health and Medical Research Council of Australia [APP1008014]This work was supported by a Project Grant from the National Health and Medical Research Council (NHMRC) Australia to N. K. [NHMRC Grant APP1008014]. We are thankful to the Nuclear Magnetic Resonance Facility and the Bioanalytical Mass Spectrometry Facility (BMSF) in the Mark Wainwright Analytical Centre at UNSW Sydney for the opportunity of using their instruments

Synthesis of Imine and Amine-Linked Macrocycles Containing Tris-Indoles

The synthesis of 21-membered imine-and amine-linked tris-indole macrocycles starting from 7-nitroethylindoles is described. The 7-nitroethylindoles are converted to 2,2'-diindolylmethanes and the nitro groups reduced to amino. The resulting diamines undergo reactions with indole-2,7-dicarbaldehydes to form the macrocyclic imines, which can subsequently be reduced to the macrocyclic amines.University of New South Wales; Turkish GovernmentTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK)The authors thank the University of New South Wales and the Turkish Government for their financial support