A Synthetic Route to Tetrahydro-1-azepino[4,3,2-]indoles via Ring-Opening Cyclization of Activated Azetidines with 4-Bromoindole: Toward a Vasopressin V2 Receptor Antagonist.

A simple one-pot, two-step strategy for the synthesis of tetrahydro-1-azepino[4,3,2-]indoles via Lewis acid-catalyzed S2-type ring opening of activated azetidines with 4-bromoindole, followed by a Pd-catalyzed intramolecular C-N cyclization reaction, with good to excellent yields is described. Utilizing this protocol, the vasopressin V2 receptor antagonist precursor has been synthesized easily. Enantioenriched tetrahydro-1-azepino[4,3,2-]indoles were obtained by starting from enantiopure azetidine.

Unconventional mechanism of action and resistance to rapalogs in renal cancer.

mTORC1 is aberrantly activated in renal cell carcinoma (RCC) and is targeted by rapalogs. As for other targeted therapies, rapalogs clinical utility is limited by the development of resistance. Resistance often results from target mutation, but mTOR mutations are rarely found in RCC.

A new species of Fusigobius (Teleostei: Gobiidae) from the Red Sea and Gulf of Aden.

The gobiid species, Fusigobius humerosus sp. nov., is described based on 12 type and 18 non-type specimens collected from the Red Sea and Gulf of Aden.

Stereoselective Routes to Hexahydropyrroloindoles and Tetrahydropyrroloquinolines from Activated Aziridines and Electron Deficient 3-Indoles.

An unprecedented and novel synthetic route to hexahydropyrrolo[2,3-]indoles bearing -contiguous stereocenters with excellent stereoselectivities (ee of >99%, dr of ≤99:1) has been disclosed that proceeds through the ring opening of activated aziridines with electron deficient 4-substituted indoles followed by a novel cyclization in a domino fashion, thereby obviating the use of 3-substituted indoles as the prerequisite nucleophile. Another efficient synthetic route to tetrahydropyrrolo[4,3,2-]quinolines in excellent yields (≤93%) and excellent enantioselectivity (ee of >99%) has been established via ring opening of activated aziridines with 4-bromo-1-methyl-1-indole at relatively higher temperatures followed by Cu(I)-catalyzed intramolecular C-N cyclization in the same pot. The stability and the formation of products at different temperatures are explained by computational studies.