Alkaloids of the Australian Rutaceae: Pentaceras australis Hook. F. III. Identification of 4-Methylthiocanthin-6-one

1952 ◽  
Vol 5 (4) ◽  
pp. 768 ◽  
Author(s):  
ER Nelson ◽  
JR Price
Keyword(s):  
Carboxylic Acid ◽  
Hydrochloric Acid ◽  
Acrylic Acid ◽  
Absorption Spectra ◽  
Acid Chloride ◽  
Ethyl Esters ◽  
Methyl Mercaptan ◽  
Malonic Ester ◽  
Alcoholic Alkali ◽  
Lactam Ring

The alkaloid C15H10OSN2 occurring in the bark of Pentaceras australis Hook. f. is shown to be 4-methylthiocanthin-6-one. The lactam ring is opened by alcoholic alkali giving 2-methylthio-2-(1'-β-carbolyl)acrylic acid, followed by the elimination of methyl mercaptan and recyclization to 4-hydroxycanthin-6-one. Confirmation of the relation- ship of the alkaloid to canthinone is provided by (i) the ultraviolet absorption spectra, (ii) the formation of methyl mercaptan and 4,5-dihydrocanthine by treatment with zinc and hydrochloric acid, and (iii) the formation, by treatment with Raney nickel, of canthinone, 4,5-dihydrocanthinone, or the methyl or ethyl esters of β-carbolylpropionic acid, depending on the conditions employed. The alkaloid has been synthesized from β-carboline-1-carboxylic acid by conversion of the acid chloride with malonic ester, followed by cyclization, to 4-hydroxycanthinone, thence to 4-chlorocanthinone which with potassium methyl mercaptide yields 4-methylthiocanthinone. The low basicity of the alkaloid is discussed, particularly in relation to the basicity of 4-methoxy- canthinone.

Alkaloids of the Australian Rutaceae: Pentaceras australis Hook. F. I. Isolation of the Alkaloids and Identification of Canthin-6-one

1952 ◽  
Vol 5 (2) ◽  
pp. 387 ◽  
Author(s):  
HF Haynes ◽  
ER Nelson ◽  
JR Price
Keyword(s):  
Carboxylic Acid ◽  
Acrylic Acid ◽  
Trans Isomer ◽  
Total Yield ◽  
Forest Tree ◽  
Ring System ◽  
Root Bark ◽  
Mature Trees ◽  
Plant Kingdom ◽  
Lactam Ring

Three alkaloids, with molecular formulae C14H8ON2, C15H10O2N2, and C15H10OSN2,, have been isolated from the ram-forest tree Pentaceras australis Hook. f. All three are present in the bark of mature trees, the total yield of alkaloids varying from c. 0.2 per cent. (branch bark) to c. 1 per cent. (root bark). The wood contains 0.2 per cent. of a mixture of two of the alkaloids, C14H8ON2 and C15H10OSN2, while the leaves contain less than 0.01 per cent. of a mixture in which the alkaloids C14H8ON2 and C15H10O2N2 are present.The alkaloid C14H8ON2 is shown to be representative of a ring system not previously found In the plant kingdom. It is canthm-6-one (II). The principal reactions on which this structure is based are (a) oxidation of the alkaloid to β-carboline-1-carboxylic acid and (b) the reversible opening of a lactam ring with alkali to give cis-2-(1'-β-carbolyl) acrylic acid (III) which may be transformed to the trans-isomer from which the alkaloid is not regenerated. Other reactions of the alkaloid support the canthinone structure. Among the compounds described is a dihydro-derivative (XI) of the parent base canthine

scholarly journals Regioselective Base-induced Condensations of Acrylic Acid Derivatives

1999 ◽  
Vol 23 (3) ◽  
pp. 174-175
Author(s):  
E. Abdel-Ghani
Keyword(s):  
Carboxylic Acid ◽  
Acrylic Acid ◽  
Dicarboxylic Acid ◽  
Ethyl Acetoacetate ◽  
Tobacco Necrosis Virus ◽  
Necrosis Virus ◽  
Antiviral Activities

The orientation of cyclization of the reaction of methyl aroylacrylate (1) and aroylacrylic acid (8) with ethyl acetoacetate and/or thiourea leading to the formation of 4-aroylmethylcyclopentane-1,3-dione (2) 5-aryl-3-oxocyclohexene-1,2-dicarboxylic acid (9), 2-imino-5-aroylmethylthiazolidin-4-one (11) and 6-aryl-2-sulfonylpyrimidine-4-carboxylic acid (14) depends on the medium employed; some compounds show moderate antiviral activities against tobacco necrosis virus.

scholarly journals 3-Propionyl-thiazolidine-4-carboxylic acid ethyl esters: a family of antiproliferative thiazolidines

MedChemComm ◽  
2015 ◽  
Vol 6 (1) ◽  
pp. 90-93 ◽  
Author(s):  
F. Esra Önen-Bayram ◽  
Kerem Buran ◽  
Irem Durmaz ◽  
Barkin Berk ◽  
Rengul Cetin-Atalay
Keyword(s):  
Carboxylic Acid ◽  
Physicochemical Properties ◽  
Ethyl Esters

Modification at the 2-position of the apoptosis-inducing compound ALC 67 enables tuning of its physicochemical properties.

Three new staphylonuclear chloromolybdates : K6Mo3Cl12, (NH4)7Mo3Cl13,H2O, and Cs6Mo4Cl16

1965 ◽  
Vol 18 (3) ◽  
pp. 271 ◽  
Author(s):  
IR Anderson ◽  
JC Sheldon
Keyword(s):  
Solid State ◽  
Hydrochloric Acid ◽  
Absorption Spectra ◽  
Oxidation State ◽  
Chlorine Atom ◽  
Reducing Agents ◽  
Ammonium Salts ◽  
Chlorine Atoms ◽  
Regular Triangle ◽  
New Compounds

The new compounds, K6Mo3IICl12; (NH4)7Mo3IICl13.H2O; and Cs6Mo4Cl16 (containing molybdenum in oxidation state +2.5) have been precipitated by the appropriate cation from solutions of molybdenum(II) acetate in 12M hydrochloric acid. The absorption spectra of potassium and ammonium salts are similar in the solid state and solution. Since the compounds are strong reducing agents and short-lived in solution, their formulation as a staphylonuclear (i.e. metal-clustered) trimer or tetramer rests on their diamagnetism, stoicheiometry, and spectral similarities. It is proposed that the chloromolybdates adopt entirely novel, compact polymers by stacking the chlorine atoms into "close packed" layers. The Mo3Cl13 group consists of two layers of chlorine atoms (seven and six) generating three octahedral locations for the molybdenum atoms at the corners of a regular triangle. The Mo3Cl12 group is similar but deficient in one chlorine atom. The Mo4Cl16 group is related to Mo3Cl13 and consists of three layers of chlorine atoms (seven, six, and three) providing four octahedral locations for the molybdenum atoms at the corners of a tetrahedron.

Some studies in inorganic complexes. XXV. Cobalt(II) and nickel(II) complexes of 2-Acetamidopyridine and 2-Aminomethyl-6-rnethylpyridine, and the cobalt(II) complex of 2-Methylpyridine-6-carboxylic acid

1969 ◽  
Vol 22 (9) ◽  
pp. 1841 ◽  
Author(s):  
KH Shaw ◽  
GJ Sutton
Keyword(s):  
Magnetic Properties ◽  
Carboxylic Acid ◽  
Absorption Spectra ◽  
Infrared Spectra ◽  
Reflectance Spectra ◽  
Inorganic Complexes

Complexes of cobalt(II) and nickel(II) with the ligands 2- acetamidopyridine (acpy) and 2-aminomethyl-6-methylpyridine (mepic) have been prepared and studied. They included [Co(acpy)2X2], [Co(mepic)2X2], [Ni(acpy)2X2], and [Ni-(mepic)2X2], in which X is Cl, Br, I, or NCS; [Co(acpy)2(NO3)2], [Co(mepic)2(NO3)2], [Ni(acpy)2(NO3)2], [Ni(mepic)3NO3]NO3, [Co(acpy)3](ClO4)2, [Co(mepic)3](ClO4)2, [Co(mepic)3](CoCl4), [Ni(acpy)2(H2O)2](ClO4)2, and [Ni(mepic)2(H2O)2](ClO4)2. The inner complex of 2-methylpyridine-6- carboxylic acid [Co(mepiac)2,2H2O)] was also isolated. In all cases, the magnetic properties, conductances, reflectance spectra, absorption spectra, and infrared spectra are in agreement with the concept that they are spin-free, six-coordinate octahedral complexes. The substance [Ni(mepic)2NO3]NO3 contains both bidentate and ionic nitrate.

α-CYANO-β-ARYLACRYLIC ACIDS

1945 ◽  
Vol 23b (2) ◽  
pp. 84-87 ◽  
Author(s):  
C. Y. Hopkins ◽  
Mary Chisholm ◽  
Ruth Michael
Keyword(s):  
Carboxylic Acid ◽  
Acrylic Acid

α-Cyano-β-arylacrylic acids have been prepared by condensing the following aldehydes with sodium cyanoacetate: 1-naphthaldehyde, 2,3-dimethoxybenzaldehyde, 3,4-diethoxybenzaldehyde, 6-chloropiperonal, 4-isopropylbenzaldehyde, 2-acetoxy-3-methoxybenzaldehyde, 2-hydroxy-3-methoxybenzaldehyde. The last-named gave α-cyano-β (2-hydroxy-3-methoxyphenyl) acrylic acid, which was readily converted to 8-methoxycoumarin-3-carboxylic acid.

ChemInform Abstract: A New Synthesis of 1-Aryl-5-cyano-1H-pyrazole-4-carboxylic Acid Ethyl Esters.

ChemInform ◽  
1989 ◽  
Vol 20 (13) ◽  
Author(s):  
J. R. BECK ◽  
S. A. ACKMANN ◽  
M. A. STASZAK ◽  
F. L. WRIGHT
Keyword(s):  
Carboxylic Acid ◽  
Ethyl Esters ◽  
New Synthesis

Alkaloids of the Australian Rutaceae: Melicope fareana. IV. Some Reactions of 1-Methyl-4-quinolone-3-carboxyic Acid, a Degradation Product of the Alkaloids

1949 ◽  
Vol 2 (2) ◽  
pp. 272 ◽  
Author(s):  
JR Price
Keyword(s):  
Nitric Acid ◽  
Carboxylic Acid ◽  
Hydrochloric Acid ◽  
Degradation Product ◽  
Carboxyl Groups ◽  
Methyl Groups ◽  
Derivatives Of

Melicopine, melicopidine, and melicopicine are each oxidized by nitric acid to the same acid, C11H9O3N. Decarboxylation gives 1-methyl-4-quinolone (I) and the acid is shown to be 1-methyl-4-quinolone-3-carboxylic acid (II). The 3- and 6- mononitro-, 3,6-dinitro-, and 2-hydroxy-3,6-dinitro- derivatives of 1-methyl-4-quinolone have been prepared and the orientation of the substituents established by oxidation of the hydroxydinitro- compound to 5-nitro-N-methylanthranilic acid. 1-Methy1-4-quinolone-3-carboxylic acid is readily converted to a tetrahydro- derivative. The carboxyl groups in II and in the tetrahydro- acid are reduced by zinc and hydrochloric acid to methyl groups.

ISOLATION AND IDENTIFICATION OF TWO PHENAZINES FROM A STRAIN OF PSEUDOMONAS AUREOFACIENS

1965 ◽  
Vol 43 (9) ◽  
pp. 1055-1062 ◽  
Author(s):  
J. I. Toohey ◽  
C. D. Nelson ◽  
G. Krotkov
Keyword(s):  
Carboxylic Acid ◽  
Absorption Spectra ◽  
Infrared Absorption ◽  
Chemical Properties ◽  
The Other ◽  
Isolation And Identification ◽  
Pseudomonas Aureofaciens ◽  
Infrared Absorption Spectra

A method is described for the purification of two phenazine compounds from cultures of a strain of Pseudomonas aureofaciens. The chemical properties of the compounds are described and the ultraviolet, visible, and infrared absorption spectra are shown. One compound is identified as phenazine-1-carboxylic acid and the other is probably 2-hydroxyphenazine-1-carboxylic acid.

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