This chapter contains sections titled: Introduction Preparation of Amidines Synthetic Uses of Amidines References

Hydrazides of amino acids and acylamino acids were condensed with 2-chlorobenzaldehyde or 2-chloroacetophenone. The hydrazidones obtained exhibited antihypertensive activity. In a few cases the activities were similar or higher than those of the reference compounds.

The modified alpha-cyclodextrin system having four nicotinate groups with an ABDE symmetry presents two pairs of preferentially cis-coordinating pyridyl ligands. The molecule in dmso-d6 has been shown by H-1 NMR to complex two cis-PtCl2 moieties. The observed non-equivalence of the pyridyl ligands may be explained by a molecular graphics study which places the metal above and outside the rim of the alpha-cyclodextrin with the two coordinating ligands in sites parallel and antiparallel to the molcular axis.

A nucleobase derivative of β-cyclodextrin was used to form a highly soluble inclusion complex of ellipticine. The reality of inclusion and the formation of a π-π interaction between host and guest were established by NMR.

The effects of MP 518, an acylated 2-chlorobenzylidene hydrazidone derivative with antihypertensive properties were investigated on the Ca current, ICa, recorded under whole-cell patch-clamp in single frog ventricular cells. MP 518 (1-100 microM) had no effect on ICa under control conditions. However, at 10 microM it significantly increased the beta-adrenergic stimulated ICa, an effect similar to that of isobutylmethyl-xanthine (IBMX), a non-specific phosphodiesterase inhibitor. The effects of MP 518 and IBMX were not, however, additive. This positive effect was also observed with both compounds, MP 518 and IMBX, when a submaximal dose of cyclic AMP was intracellularly perfused. In the presence of IBMX or at a high concentration (100 microM), MP 518 had a negative effect on beta-adrenergic stimulated ICa. It was thus considered that the main effect of MP 518 is an antiphosphodiesterase activity, since the increase in ICa induced by low concentrations of MP 518 could be related to inhibition of cAMP degradation; however, at higher concentrations, MP 518 antagonizes beta-adrenergic stimulation, possibly at several levels. Such an antiphosphodiesterase activity can account for the vasorelaxant effects as well as the tachycardic effects of MP 518.

Biotransformation of the synthetic substrate, ethyl 2-acetylamino-2-carbethoxy-4-(phenylsuphinyl)- butanoate, by cell suspension cultures of Catharanthus roseus and Thevetia neriifolia was investigated. It was found that only three of six cell lines of T. neriifolia tested biotransformed the test substrate into a new product, ethyl 2-acetylamino-2-carbethoxy-4-(phenylsulphonyl)-butanoate, through a selective oxidizing process not previously described. Such a biotechnological process could be of great interest for the production of new chemical compounds.

effective and straightforward route has been accomplished for the synthesis of hexahydrodibenzofurans based on rearrangement of a spirodihydrocoumarin.

Treatment of per-2-O-tosyl-cyclodextrins with K2CO3 allows the synthesis of cyclomannoepoxides 2a, 2b, ZC in high yields (>90%). The glncopyranose structure of 2a, 2b, 2c, is assigned from the H-1 coupling pattern (J(1,2) = 0 Hz, J(2,3) = 3.5 Hz, J(3,4) = 0 Hz), as a half chair conformation. 2b shows surfactant properties in water. Full analysis of the NMR spectra of 2a, 2b, 2c has been carried out. The inclusion and hydrolytic properties of 2 differ from those of the parent cyclodextrins as a result of a lack of secondary hydroxyl groups capable of forming hydrogen-bonded dimers.

Simultaneous complexation of metal ions and inclusion of organic molecules is possible with the alpha-cyclodextrin derivative 6A,6C,6E-tri-amino-N,N',N"-tris(2,3-dihydroxybenzoyl)-pentadeca-O-methyl-alpha-cyclodextrin (1) shown schematically here. The NMR spectra of 1, 1 + Fe3+, 1 + Al3+, and 1 + Al3+ + p-nitrophenolate support this thesis.

Substitution of the primary hydroxyl groups of alpha-cyclodextrin by nicotinate groups in an ABDE conformation yields a molecule having two pairs of pyridyl ligands. The compound complexes CoCl2 and CuBr2 in methanol or acetone to yield 1:2 complexes which are soluble in chloroform. The electronic spectrum of the blue CoCl2 complex is almost identical to that of Co(Py)2Cl2, implying a molecular complex with a tetrahedral geometry. The molecular graphics study of this complex shows the two CoCl2 groups positioned over and outside of the rim of unoccupied alpha-cyclodextrin.

DIBAL-H-mediated desilylation reaction has been extended to sterically even more hindered 6-O-thexyldimethylsillyl-2,3-di-O-alkyl protected CD substrates. It was found the reductive desilylations are still regioselective to afford the 6A- and 6A,6D-O-didesilylated products. By changing the amount of reagent used, each of the products can be isolated as a majority. The alkyl groups appear to be compatible with methyl, benzyl, and even the more versatile allyl groups.

Monosubstitution at the O-6 position of β-cyclodextrin by a β-N-glucosyl residue has been achieved with a spacer C9 diamide as the interglycosidic linkage. The new glycosyl derivative has been characterised by 1H N.M.R. (COSY-RCT), is much more soluble (200g.1−1) in water and has been shown to retain the capacity to include and to enhance the solubility of pharmacologically active molecules.

Heteroarylmethylation of halogenobenzonitriles in the presence of air (O2) gives 1-hydroxy-3-oxo-1-aryl-1H,3H-isoindoles in liquid ammonia. A "one-pot" or two- step synthesis is described and a mechanism is proposed.

Angewandte ChemieVolume 104, Issue 10 p. 1402-1404 Zuschrift Synthese und Komplexierungsverhalten eines auf Cyclodextrin beruhenden Siderophors Dr. Anthony W. Coleman, Corresponding Author Dr. Anthony W. Coleman CNRS, Laboratoire de Chimie Organique Centre Pharmaceutique, Université de Paris Sud F-92290 Chàtenay-Malabry (Frankreich)CNRS, Laboratoire de Chimie Organique Centre Pharmaceutique, Université de Paris Sud F-92290 Chàtenay-Malabry (Frankreich)Search for more papers by this authorDr. Chang-Chun Lin, Dr. Chang-Chun Lin CNRS, Laboratoire de Chimie Organique Centre Pharmaceutique, Université de Paris Sud F-92290 Chàtenay-Malabry (Frankreich)Search for more papers by this authorProf. Dr. Marcel Miocque, Prof. Dr. Marcel Miocque CNRS, Laboratoire de Chimie Organique Centre Pharmaceutique, Université de Paris Sud F-92290 Chàtenay-Malabry (Frankreich)Search for more papers by this author Dr. Anthony W. Coleman, Corresponding Author Dr. Anthony W. Coleman CNRS, Laboratoire de Chimie Organique Centre Pharmaceutique, Université de Paris Sud F-92290 Chàtenay-Malabry (Frankreich)CNRS, Laboratoire de Chimie Organique Centre Pharmaceutique, Université de Paris Sud F-92290 Chàtenay-Malabry (Frankreich)Search for more papers by this authorDr. Chang-Chun Lin, Dr. Chang-Chun Lin CNRS, Laboratoire de Chimie Organique Centre Pharmaceutique, Université de Paris Sud F-92290 Chàtenay-Malabry (Frankreich)Search for more papers by this authorProf. Dr. Marcel Miocque, Prof. Dr. Marcel Miocque CNRS, Laboratoire de Chimie Organique Centre Pharmaceutique, Université de Paris Sud F-92290 Chàtenay-Malabry (Frankreich)Search for more papers by this author First published: Oktober 1992 https://doi.org/10.1002/ange.19921041029Citations: 7AboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Citing Literature Volume104, Issue10Oktober 1992Pages 1402-1404 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. RelatedInformation

Use of the t-butyl dimethylsilyl group to selectively protect the primary OH-6 function allows the facile regioselective per-tosylation of the secondary OH-2 function. The t-butyldimethylsilyl group can be removed without attack at the tosyl function.

The action of sodium cyanide ongem -diphenyl-chloropropanone under phase transfer conditions in the presence of 15-crown-5 yields the title compound as a minor product. The crystal structure of this complex reveals that, in the solid state, the [15-crown-5-Na+] guest species is found within a loose cage of diphenylethyl diphenyl cyanoacetonate molecules with one open side of the cage blocked by an adjacent 15-crown-5 molecule. Colourless crystals of the compound belong to the monoclinic space groupP21/n witha = 12,255(2) Å,b = 13,005(1) Å,c = 23,433(2) Å, β = 95,92(1) ° andDc = 1.23 g cm−3 forZ = 4.

Antihypertensive actions of hydrazidones: study of acylated 2-cholo benzilidenhydrazines. A series of acylated hydrazones: o-Cl-C6H4-C(R1) = N-NH-CO-R, have been prepared and evaluated on spontaneous hypertensive rats (SHR). The more active compounds present a hydroxyl in position-alpha to the acyl group and R1 is a small alkyl group.

Les métabolites de l'acide barbiturique étudié sont synthétisés par des méthodes chimiques variées. Leur comportement dans des conditions biomimétiques est rapporté. L'administration au Chien et au Rat est réalisée: 8,8 ± 0,5% (Chien) ou 9,5 ± 0,4% (Rat) de composé non-transformé ainsi que 45,4 ± 1,7% (Chien) ou 39,0 ± 1,9% (Rat) de composé résultant d'une oxydation hépatique sont obtenus à partir des urines. La comparaison de ces résultats avec ceux qui ont été obtenus pour des barbituriques voisins confirme la relation entre lipophilie et taux de biotransformation.