Use of malonic acid derivatives for the construction of substituted side chains in the position 17β of steroids

1982 ◽  
Vol 47 (4) ◽  
pp. 1240-1251 ◽  
Author(s):  
Pavel Drašar ◽  
Vladimír Pouzar ◽  
Ivan Černý ◽  
Miroslav Havel ◽  
Sofia N. Ananchenko ◽  
...  
Keyword(s):  
Malonic Acid ◽  
Ethyl Cyanoacetate ◽  
Diethyl Malonate ◽  
Side Chain ◽  
Knoevenagel Reaction ◽  
Side Chains ◽  
Condensation Products ◽  
Malonic Acid Derivatives ◽  
Derivatives Of ◽  
Dioxane Ring

Using the Knoevenagel reaction condensation products of 3β-acetoxyandrost-5-en-17-one with diethyl malonate, ethyl cyanoacetate and malononitrile were prepared which converted to derivatives of 3β-hydroxypregn-5-en-21-oic acid. Reductions and oxidations of the double bonds in the positions 5,6 and 17,20 and the stereochemistry at atoms C(17) and C(20) of some derivatives were also investigated. From derivatives of 23,24-dinorchola-5,17(20)-diene-21,22-diol compounds with a 1,3-dioxane ring in the side chain were prepared.

scholarly journals Synthesis of New Derivatives of BEDT-TTF: Installation of Alkyl, Ethynyl, and Metal-Binding Side Chains and Formation of Tris(BEDT-TTF) Systems

2021 ◽  
Vol 7 (8) ◽  
pp. 110
Author(s):  
Songjie Yang ◽  
Matteo Zecchini ◽  
Andrew Brooks ◽  
Sara Krivickas ◽  
Desiree Dalligos ◽  
...  
Keyword(s):  
Metal Binding ◽  
Tricarboxylic Acid ◽  
Metal Salts ◽  
Side Chain ◽  
Side Chains ◽  
Ethynyl Group ◽  
X Ray ◽  
Transition Metal Salts ◽  
Alkyl Side Chains ◽  
Derivatives Of

The syntheses of new BEDT-TTF derivatives are described. These comprise BEDT-TTF with one ethynyl group (HC≡C-), with two (n-heptyl) or four (n-butyl) alkyl side chains, with two trans acetal (-CH(OMe)2) groups, with two trans aminomethyl (-CH2NH2) groups, and with an iminodiacetate (-CH2N(CH2CO2−)2 side chain. Three transition metal salts have been prepared from the latter donor, and their magnetic properties are reported. Three tris-donor systems are reported bearing three BEDT-TTF derivatives with ester links to a core derived from benzene-1,3,5-tricarboxylic acid. The stereochemistry and molecular structure of the donors are discussed. X-ray crystal structures of two BEDT-TTF donors are reported: one with two CH(OMe)2 groups and with one a -CH2N(CH2CO2Me)2 side chain.

Comparative study of dG affinity vs. DNA methylation modulating properties of side chain derivatives of procainamide: insight into its DNA hypomethylating effect

RSC Advances ◽  
2016 ◽  
Vol 6 (7) ◽  
pp. 5350-5358 ◽  
Author(s):  
R. L. Gawade ◽  
D. K. Chakravarty ◽  
J. Debgupta ◽  
E. Sangtani ◽  
S. Narwade ◽  
...  
Keyword(s):  
Dna Methylation ◽  
Comparative Study ◽  
Structural Features ◽  
Side Chain ◽  
Side Chains ◽  
Hypomethylating Agents ◽  
Derivatives Of ◽  
Insight Into

Structural features of side-chains govern the association of procainamide and its derivatives with dG base of CpG rich DNA, which may differentially hinder the activity of DNMT-1, thereby they act as DNA hypomethylating agents.

23.—The Synthesis of Derivatives of Acenaphthenone

1974 ◽  
Vol 71 (4) ◽  
pp. 279-283 ◽  
Author(s):  
Michael J. Bedford ◽  
Douglas A. Crombie
Keyword(s):  
Polymeric Material ◽  
Malonic Acid ◽  
Hydroxy Acid ◽  
Ethyl Cyanoacetate ◽  
Geometric Isomer ◽  
Unsaturated Ester ◽  
Image Position ◽  
Derivatives Of

Acenaphthenequinone (I) condensed with ethyl cyanoacetate in ethanol to give the unsaturated ester (IIIb) while condensation with malonic acid in toluene in the presence of diethylamine gave the hydroxy acid (IIa). Esterification of this acid gave an ester (IIb) which could also be obtained by condensation of acenaphthenequinonewith ethyl hydrogen malonate. The acid (IIa) on dehydration gave 2-oxo-Δ1,α-acenaphtheneacetic acid (IIIa) of m.p. 230°C. This result seems to be in conflict with that of Rodionov and Federova (1950) who reported a m.p. of 160° for the acid (IIIa) which they obtained directly by condensation of acenaphthenequinone with malonic acid in ethanol in the presence of ammonia. Our efforts to repeat their result gave only impure polymeric material and it seems unlikely, therefore, that their product was simply the geometric isomer of our acid.

ChemInform Abstract: STEROIDS. CCLXIII. USE OF MALONIC ACID DERIVATIVES FOR THE CONSTRUCTION OF SUBSTITUTED 17β-SIDE CHAINS OF STEROIDS

1982 ◽  
Vol 13 (30) ◽  
Author(s):  
P. DRASAR ◽  
V. POUZAR ◽  
I. CERNY ◽  
M. HAVEL ◽  
S. N. ANANCHENKO ◽  
...  
Keyword(s):  
Malonic Acid ◽  
Side Chains ◽  
Malonic Acid Derivatives

Preparation of Derivatives of 2-Cyano-3-(5-N-arylamino- or 5-N-Alkyl-N-phenylamino-2-furyl)propenoic Acids

1997 ◽  
Vol 62 (7) ◽  
pp. 1105-1113 ◽  
Author(s):  
Peter Šafář ◽  
František Považanec ◽  
Pavel Čepec ◽  
Naďa Prónayová
Keyword(s):  
Malonic Acid ◽  
Aromatic Amines ◽  
Propenoic Acid ◽  
Malonic Acid Derivatives ◽  
Hydrolysis Of ◽  
Derivatives Of

(5-Bromo-2-furyl)methylidenemalonodinitrile (1) reacted with substituted aromatic amines under formation of (5-N-arylamino-2-furyl)methylidenemalonodinitriles 2a-2h whereas no reaction was observed with N-alkyl-N-phenylamines. Derivatives of 2-cyano-3-(5-N-alkyl-N-phenylamino-2-furyl)- propenoic acid 5a-5o were prepared by reaction of the corresponding N-alkylanilines with 5-bromo-2-furancarbaldehyde, followed by hydrolysis of the obtained Eiji salts and reaction with malonic acid derivatives.

Contribution of Side Chains to Karbutilate Mode of Action

Weed Science ◽  
1975 ◽  
Vol 23 (5) ◽  
pp. 425-427 ◽  
Author(s):  
R. S. Hammerschlag ◽  
J. L. Hilton ◽  
P. G. Bartels ◽  
D. E. Moreland
Keyword(s):  
Seedling Growth ◽  
Mode Of Action ◽  
Acid Ester ◽  
Specific Inhibitor ◽  
Side Chain ◽  
Side Chains ◽  
Inhibiting Action ◽  
Alkyl Carbamate ◽  
Derivatives Of ◽  
Growth Inhibiting

Inhibition of seedling growth and four assays for inhibition of photosynthesis were used to compare karbutilate [tert-butylcarbamic acid ester with 3-(m-hydroxyphenyl)-1,1-dimethylurea] with derivatives of karbutilate in which either the urea or carbamate side chain was missing. Karbutilate was a more potent, more presistent, and more specific inhibitor of photosynthesis than the phenylurea derivative fenuron (1,1-dimethyl-3-phenylurea) that would be formed by removal of the carbamate side chain. However, karbutilate did not exert the growth-inhibiting action observed for the alkyl carbamate derivative phenyl-N-tert-butylcarbamate, formed by removal of the urea side chain, which does not affect photosynthesis at concentrations below 10-3M.

ChemInform Abstract: An Efficient Method for the Preparation of Mono α-Aryl Derivatives of Diethyl Malonate and Ethyl Cyanoacetate Using Ethyl-1-imidazole Carbamate (EImC).

ChemInform ◽  
2012 ◽  
Vol 43 (25) ◽  
pp. no-no
Author(s):  
Manoranjan Behera ◽  
R. Venkat Ragavan ◽  
M. Sambaiah ◽  
Balaiah Erugu ◽  
J. Rama Krishna Reddy ◽  
...  
Keyword(s):  
Efficient Method ◽  
Ethyl Cyanoacetate ◽  
Diethyl Malonate ◽  
Derivatives Of

An efficient method for the preparation of mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate using ethyl-1-imidazole carbamate (EImC)

2012 ◽  
Vol 53 (9) ◽  
pp. 1060-1062 ◽  
Author(s):  
Manoranjan Behera ◽  
R. Venkat Ragavan ◽  
M. Sambaiah ◽  
Balaiah Erugu ◽  
J. Rama Krishna Reddy ◽  
...  
Keyword(s):  
Efficient Method ◽  
Ethyl Cyanoacetate ◽  
Diethyl Malonate ◽  
Derivatives Of
Sign in / Sign up

Export Citation Format

Share Document