Charles F. Huebner
Bio: Charles F. Huebner is an academic researcher from Ciba Specialty Chemicals. The author has contributed to research in topic(s): Rauwolfia alkaloid & Deserpidine. The author has an hindex of 11, co-authored 32 publication(s) receiving 447 citation(s).
01 Jan 1954-Helvetica Chimica Acta
TL;DR: Reserpine, C33H40O9N2, has been isolated from Rauwolfia serpentina Benth as discussed by the authors and is an ester alkaloid yielding reserpic acid, 3,4,5-trimethoxybenzoic acid and methanol on hydrolysis.
Abstract: Reserpine, C33H40O9N2, has been isolated from Rauwolfia serpentina Benth. Reserpine is an ester alkaloid yielding reserpic acid, 3,4,5-trimethoxybenzoic acid and methanol on hydrolysis. Degradation products of reserpic acid make it likely that reserpic acid is a yohimbane derivate, and a hypothetical structure for reserpine has been put forward which is in agreement with the facts known so far.
TL;DR: The preparation of a series of 1-glutarylindoline-2(S)-carboxylic acid derivatives, 6a-v and 21a-c, is described and the structure-activity relationship of the series is discussed.
Abstract: The preparation of a series of 1-glutarylindoline-2(S)-carboxylic acid derivatives, 6a-v and 21a-c, is described The above compounds were tested for inhibition of angiotensin converting enzyme The structure-activity relationship of the series is also discussed Compound 6u, the most potent member of the series, had an in vitro IC50 of 48 X 10(-9) M Compound 6v, an ethyl ester of 6u, lowered blood pressure 70 mm in spontaneous hypertensive rats at an oral dose of 30 mg/kg
25 Nov 2005-Natural Product Reports
TL;DR: This review covers the literature on simple indole alkaloid and those with a nonrearranged monoterpenoid unit and newly isolated alkaloids, structure determinations, total syntheses and biological activities.
Abstract: Covering: 2005. Previous review: Nat. Prod. Rep., 2005, 22, 761 This review covers the literature on simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Newly isolated alkaloids, structure determinations, total syntheses and biological activities are included.
TL;DR: The potential synthetic utility of the present method for the practical asymmetric synthesis of structurally diverse natural and unnatural alpha-amino acids has been demonstrated by its successful application to the facile asymmetric syntheses of (S)-N-acetylindoline-2-carboxylate, a key intermediate in the synthesis of the ACE inhibitor, and l-Dopa (l-3,4-dihydroxyphenylalanine) ester and its analogue.
Abstract: A series of C2-symmetric chiral quaternary ammonium bromides 10 and 11 have been designed as a new, purely synthetic chiral phase-transfer catalyst, and readily prepared from commercially available optically pure 1,1‘-bi-2-naphthol as a basic chiral unit. The details of the synthetic procedures of each requisite chiral binaphthyl subunit have been disclosed, and the structures of the assembled N-spiro chiral quaternary ammonium bromides 11a and 11f were unequivocally determined by single-crystal X-ray diffraction analysis. The reactivity and selectivity of these chiral ammonium bromides as chiral phase-transfer catalysts have been evaluated in the asymmetric alkylation of the benzophenone Schiff base of glycine ester 7 under mild liquid−liquid phase-transfer conditions, and the optimization of the reaction variables (solvent, base, and temperature) has also been conducted. Further, the scope and limitations of this asymmetric alkylation have been thoroughly investigated with a variety of alkyl halides, in...
01 Oct 1985-Medicinal Research Reviews
TL;DR: It is hoped that some of the insights to be derived from the SAR and structural studies done with ACE inhibitors will be applicable to other enzyme targets as well.
Abstract: Orally-active angiotensin-converting enzyme inhibitors are rapidly establishing themselves in the therapy of hypertension and congestive heart failure. Concerted efforts in a number of laboratories have now led to the discovery or synthesis of an unparalleled variety of potent inhibitors. The manner in which several of these inhibitors bind to ACE is beginning to be understood. It is hoped that some of the insights to be derived from the SAR and structural studies done with ACE inhibitors will be applicable to other enzyme targets as well. The success of ACE inhibitors as pharmacological tools and in the clinic will also quite certainly encourage future efforts to develop new enzyme inhibitor approaches to drug therapy.
01 Jan 1958-Tetrahedron