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At least 217 records · Page 12Linked to original sources

Polymer-supported pyridine-bis(oxazoline). Application to ytterbium-catalyzed silylcyanation of benzaldehyde.

[reaction: see text] Terminal acetylenes containing hydroxy and carboxylic acid groups were subjected to Sonogashira coupling with 4-bromo-2,6-bis[(R)-4-phenyloxazolin-2-yl]pyridine and the resulting pybox derivatives were immobilized on Tentagel resins. Ytterbium(III) chloride complexes of the polymeric ligands catalyzed the addition of trimethylsilyl cyanide to benzaldehyde with 80-81% ee. The ligands were reused more than 30 times without any loss in selectivity or activity, and the metal complexes could be recovered and reused at least four times, although with slightly decreasing activity.

Journal Article↗

Action of p-(4-amidino-phenoxy)-benzaldehyde-p-amidino-phenylhydrazone dihydrochloride on Leishmania donovani infections in the golden hamster.

The chemotherapeutic effect of a new diamidine, HOE 668, the p-(4-amidino-phenoxy)-benzaldehyde-p-amidino-phenylhydrazone dihydrochloride, was compared with that of known anti-leishmanial drugs in golden hamsters infected with Leishmania donovani. The effect of HOE 668 against visceral leishmaniasis proved superior to that of pentamidine isethionate and the pentavalent antimonial drugs, sodium stibogluconate and N-methylglucamine antimoniate. However, HOE 668 can be used only experimentally because of its toxicity. Its very good anti-leishmanial action qualifies HOE 668 as a standard compound in screening tests.

Amidines↗

Benzaldehyde 2,4-dinitrophenylhydrazone.

Crystals of the title compound, C(13)H(10)N(4)O(4), were obtained from a condensation reaction of benzaldehyde and 2,4-dinitrophenylhydrazine. The molecule assumes an approximately planar E configuration. Within the dinitrophenyl moiety, the average distance for the aromatic C-C bonds close to the imino group [1.417 (3) A] is appreciably longer than the average distance for the other aromatic C-C bonds in the same phenyl ring [1.373 (3) A]. This increased distance may be a result of the overlap of the non-bonding orbital of the imino N atom with the pi orbitals of the arene. It is likely that pi-pi stacking exists in the crystal structure.

Journal Article↗

Termination of pregnancy with vaginal administration of 16, 16 dimethyl prostaglandin E2 p-benzaldehyde semicarbazone ester.

A 16,16 dimethyl prostaglandin E2 p-benzaldehyde semicarbazone ester was used for termination of pregnancy in 54 late first trimester and second trimester patients. The drug (750 microng in gelatine glycerine pessaries) was administered every four hours. Fifty patients (92-5%) aborted during the 36 hours treatment. Side effects were mild and consisted of vomiting in five patients, diarrhoea in three patients and transient pyrexia in two.

Abortifacient Agents↗

Vaginal administration of a single dose of 16, 16 dimethyl prostaglandin E2 p-benzaldehyde semicarbazone ester for pre-operative cervical dilatation in first trimester nulliparae.

A single pessary containing 0-5 mg 16, 16 dimethyl prostaglandin E2 p-benzaldehyde semicarbazone ester was used for cervical dilatation prior to vacuum aspiration in 124 first trimester nulliparae. Five hours after prostaglandin administration the cervix had dilated to 8 mm or more in 87 patients (70 per cent). The uterus was evacuated in these patients without mechanical dilatation of the cervix. In the remaining 37 patients the cervix had become soft and dilated 5 to 7 mm and further mechanical dilatation could be carried out easily. Side effects were minor and included vomiting in two patients, diarrhoea in one and transient pyrexia in two patients. There were no complications and no damage to the cervix or uterus during evacuation.

Abortion, Induced↗

Isolation and identification of the major urinary metabolite of 4-(4-fluorophenoxy)benzaldehyde semicarbazone after oral dosing to rats.

4-(4-Fluorophenoxy)benzaldehyde semicarbazone (1) is a novel anticonvulsant affording excellent protection in the rat oral maximal electroshock (MES) screen as well as having an apparent protection index of over 300. The metabolism of this compound was studied by examining the urine or rats dosed orally with 50 mg/kg of 1 which revealed that most of the drug was converted into one metabolite 2. The structure of 2 was shown by mass spectrometry to be 1-[4-(4-fluoro-phenoxy)benzoyl]semicarbazide which was confirmed by an independent synthesis. Compound 2 was bereft of activity in the rat oral MES screen when nine times the ED50 dose of 1 was administered. This datum provided strong evidence that the anticonvulsant activity of 1 and related compounds is due to the intact molecules and is not produced by breakdown products in vivo.

Animals↗

Antitumor activity of a benzaldehyde derivative.

Benzaldehyde, in the form of 4,6-benzylidene-alpha-D-glucose (BG), was given iv at a daily dose of 720-1800 mg/m2 to 65 patients with inoperable carcinoma in the advanced stages. The overall objective response rate was 55%; seven patients achieved complete response, 29 achieved partial response, 24 remained stable, and five showed progressive disease. Response was seen in various cell types. Prolongation of survival was apparent for the patients. Toxic reactions were not observed during long-term injection with BG.

Adult↗

[On structure-activity relationships of N'methyl-N'-beta-chloroethyl-benzaldehyde hydrazones (author's transl)].

The inhibition of uridine and thymidine in Ehrlich ascites cells is a basic property of the methylhydrazone structure and is reinforced by introducing a beta-chloroethyl group. This was shown by variation of the substituents at the N'-nitrogen atom of N'-methyl-N'-beta-chloroethyl-benzaldehyde hydrazone. Probably this action is due to an ethylenimmonium intermediate. This is derived from the observation that substituents which increase the nucleophilic property of the N'-nitrogen atom show a greater inhibitory effect in vitro. The therapeutic effect, however, is not enhanced when tested on the solid Ehrlich ascites tumor of mice. A better therapeutic effect resulted from introduction of chlorine atoms in positions 3 and 4 of the ring which inhbiits as well a probable metabolic hydroxylation of the ring.

Animals↗

[Affinity labeling of ribosomes from Escherichia coli with 4-(N-2-chloroethyl, N-methylamino)-benzaldehyde actyl derivatives of oligouridylates].

4-(N-2-chloroethyl-N-methylamino)-benzaldehyde acetyl derivatives of penta-., hexa, hepta-, octauridylates were used for localization of the structures organizing the mRNA-binding centre of ribosomes. These derivatives, alike free oligonucleotides, stimulate the binding of phenylalanyl-tRNA to ribosomes. Within the specific complex all the oligonucleotide derivatives alkylated the 30S ribosomal subunit. Octauridylate and hexauridylate derivatives specifically alkylated also the 50S subunit of ribosomes. Polyuridylic acid protected ribosomal subunits from alkylation. In the 30S subunit the derivatives modify 16S RNA and proteins: S4, S5, S7, S9, S13, S15, S18, S21. It was found that oligouridylate derivatives of different length alkylate different proteins.

Escherichia coli↗