The chemistry of pyrrolic compounds. XXV. The chemistry of acetal and thioacetal derivatives of pyrrolic systems

PS Clezy; CJR Fookes; DYK Lau; AW Nichol; GA Smythe

doi:10.1071/ch9740357

The chemistry of pyrrolic compounds. XXV. The chemistry of acetal and thioacetal derivatives of pyrrolic systems

Australian Journal of Chemistry ◽

10.1071/ch9740357 ◽

1974 ◽

Vol 27 (2) ◽

pp. 357 ◽

Cited By ~ 15

Author(s):

PS Clezy ◽

CJR Fookes ◽

DYK Lau ◽

AW Nichol ◽

GA Smythe

Keyword(s):

Formyl Group ◽

Derivatives Of

The synthesis of acetal and thioacetal derivatives of simple pyrroles is described. Methods are reported which allow the use of the thioacetal function as a means of protecting a formyl group in a pyrrolic molecule during the preparation of a dipyrrylmethane. By this procedure certain α-formyldipyrrylmethanes, not accessible by other methods, have been obtained.

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New Derivatives of the Vinca Rosea Alkaloids

Acta geneticae medicae et gemellologiae ◽

10.1017/s1120962300026433 ◽

1968 ◽

Vol 17 (1) ◽

pp. 193-196 ◽

Cited By ~ 1

Author(s):

James G. Armstrong

Keyword(s):

Chemical Structure ◽

Malignant Disease ◽

Cross Resistance ◽

Formyl Group ◽

Chemical Similarity ◽

Methyl Group ◽

Large Molecules ◽

Vinca Rosea ◽

Naturally Occurring ◽

Derivatives Of

Summary1. Vinblastine (VLB) and vincristine (VCR) are both naturally occurring alkaloids derived from the flowering periwinkle plant, Vinca rosea, Linn.2. Both drugs have large molecules and are very similar in chemical structure. They differ only in that VLB has a methyl group (-CH3) while VCR has a formyl group (-CHO) attached to one of the nitrogen atoms in the molecule.3. In spite of this chemical similarity, VLB and VCR differ greatly in the types of malignancy against which they are effective, their toxicities, and their potencies.4. With these differences in mind, it appeared logical to produce more alkaloids of the series by modifying one of the side chains of VLB.5. Vinglycinate sulfate (VGL), the first of these semisynthetic VLB derivatives to undergo clinical trial, has proved useful in the treatment of some patients with malignant disease. There was no cross-resistance between VGL and its parent substance, VLB, or with VCR.

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Synthesis of some 16,17-secoandrost-5-ene derivatives

Hemijska industrija ◽

10.2298/hemind100212009g ◽

2010 ◽

Vol 64 (2) ◽

pp. 81-84 ◽

Cited By ~ 1

Author(s):

Andrea Gakovic ◽

Maja Djurendic-Brenesel ◽

Evgenija Djurendic ◽

Katarina Penov-Gasi ◽

Marija Sakac

Keyword(s):

Main Reaction ◽

Main Reaction Product ◽

Formyl Group ◽

Ms Analysis ◽

Oppenauer Oxidation ◽

Derivatives Of

Starting from 3?-acetoxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), 3?-acetoxy-16,17-secoandrost-5-ene-16-nitrile (4) was synthesized by a three-stage procedure. First, the formyl group of compound 1 was reduced, to yield the alcohol 2. Compound 2 was further transformed to the mesyloxy derivative 3, whose reduction with NaBH3CN gave compound 4. Apart from compound 4 as the main reaction product, two additional products were obtained, for which the GC/MS analysis suggested that they are 8(14) and 14 derivatives of compound 4. Compound 4 was transformed into 3?-hydroxy-16,17-sesoandrost-5-ene-16-nitrile (7), the Oppenauer oxidation of which afforded 3-oxo-16,17-secoandrost-4-ene-16-nitrile (8).

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