Dibenzo[b,f]thiepin-10-carbonitrile, its 10,11-dihydro derivative, some transformation products and related compounds

1983 ◽  
Vol 48 (4) ◽  
pp. 1187-1211 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
Emil Svátek ◽  
Jiří Urban ◽  
...  
Keyword(s):  
Main Product ◽  
Cardiovascular Effects ◽  
Transformation Products ◽  
Anticonvulsant Effect ◽  
Cuprous Cyanide ◽  
High Doses ◽  
Hydrolysis Of ◽  
Related Compounds ◽  
By Products ◽  
Dichloro Derivative

Reactions of 10-bromodibenzo[b,f]thiepin (IIIa), its 2-chloro derivative IIIb and 2,8-dichloro derivative IIIc with cuprous cyanide in boiling dimethylformamide gave the carbonitriles Iabc out of which the first two were reduced with sodium borohydride to the 10,11-dihydro derivatives IVab; the amides VIIab were obtained as by-products. Alkaline hydrolysis of the nitriles IVab or their mixtures with the amides VIIab afforded the acids VIIIab. By the addition of 3-dimethylaminopropylmagnesium chloride to the nitrile Ia cis and trans-11-(3-dimethylaminopropyl)-10,11-dihydrodibenzo[b,f]thiepin-10-carbonitriles (XVIII) were obtained. Alkylation of the nitrile IVa with 2-dimethylaminoethyl chloride and 3-dimethylaminopropyl chloride resulted in the 10-(dimethylaminoalkyl) derivatives XX and XXI. A reaction of the crude cyano alcohol XXIII with phosphorus tribromide afforded the 2-bromoethyl derivative XXIV as a by-product only. The main product was the hydrobromide of the spirocyclic imidate XXX which affords by acid hydrolysis the spirocyclic lactone XXXI. An analogous sequence proceeding via the ether XXVI and the alcohol XXVII leads to the 10-(3-bromopropyl) derivative XXVIII as the main product. An attempt at preparing the same substance by alkylation of the nitrile IVa with 1,3-dibromopropane gave stereoisomeric dinitriles XXXII. At high doses the amides VIIab reveal an anticonvulsant effect, the acids VIIIab antiinflammatory actions, the basic nitrile cis-XVIII antireserpine activity and the basic nitriles XX and XXI a central depressant and pseudo-analgesic activity in addition to further peripheral and cardiovascular effects.

11-(Dimethylaminoalkyl)-6,11-dihydrodibenzo[b,e]thiepin-11-carbonitriles and some related compounds

1983 ◽  
Vol 48 (7) ◽  
pp. 1898-1909 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
Emil Svátek ◽  
Jiří Urban ◽  
...  
Keyword(s):  
Amino Acid ◽  
Potassium Hydroxide ◽  
Main Product ◽  
Sodium Hydride ◽  
Neurotropic Activity ◽  
Amide Hydrolysis ◽  
Hydrolysis Of ◽  
Related Compounds ◽  
Benzyltriethylammonium Chloride ◽  
Sodium Amide

The title compounds II and III were obtained by alkylations of 6,11-dihydrodibenzo[b,e]thiepin-11-carbonitrile (I) with 2-dimethylaminoethyl chloride and 3-dimethylaminopropyl chloride in the presence of sodium hydride or sodium amide. Hydrolysis of the nitrile II with potassium hydroxide in ethanol resulted in a small amount of the amino acid X and in the amine XI as the main product. Alkylations of I with 1,2-dibromoethane and 1,3-dibromopropane in the presence of sodium hydride gave the bromoalkylnitriles IV and V and the alkylenebisnitriles XIII and XIV. The preparation of the methylpiperazinopropyl derivative VI proved the usefulness of compounds IV and V in the synthesis of further aminonitriles of this series. Alkylation of the nitrile I with 1,2-dibromoethane in the presence of sodium hydroxide or potassium carbonate and benzyltriethylammonium chloride afforded three isomeric nitriles C17H13NS: the vinyl derivative IX, the 6,11-ethano-6H, 11H-dibenzo[b,e]thiepin derivative XV and finally the 1a,11b-dihydro-1H,7H-dibenzo[b,f]cyclopropa[d]thiocin derivative XVI. Compounds II, III, VI and XII showed some spasmolytic effects but their central neurotropic activity is insignificant.

The Stereochemistry of the Reformatsky Reaction of Methyl 4-Bromo-3-methylbut-2-enoate with β-Cyclocitral and Related Compounds

1975 ◽  
Vol 53 (13) ◽  
pp. 1943-1948 ◽  
Author(s):  
R. N. Gedye ◽  
Parkash Arora ◽  
A. H. Khalil
Keyword(s):  
Wittig Reaction ◽  
Main Product ◽  
Reformatsky Reaction ◽  
Reformatsky Reactions ◽  
Hydrolysis Of ◽  
Related Compounds ◽  
The Reformatsky Reaction

Both methyl Z- and E-4-bromo-3-methylbut-2-enoate react with β-cyclocitral in the presence of zinc to give the δ-lactone of 5-hydroxy-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-pentenoic acid as the main product, indicating an E to Z inversion during the Reformatsky reaction. Similar results were obtained in the Reformatsky reactions of the Z- and E-bromo-esters with benzaldehyde and cyclohexenecarboxaldehyde. Here hydrolysis of the Reformatsky product gave, in each case, the corresponding Z-2,E-4-acids as the main products, indicating the formation of the δ-lactone as an intermediate. The synthesis of Z- and E-β-ionylideneacetic acid and the corresponding ring demethyl analogs using a Wittig reaction is also described.

Synthesis and Tautomerism of Curcumin Derivatives and Related Compounds

2015 ◽  
Vol 68 (2) ◽  
pp. 224 ◽  
Author(s):  
Hiroyasu Taguchi ◽  
Daijiro Yanagisawa ◽  
Shigehiro Morikawa ◽  
Koichi Hirao ◽  
Nobuaki Shirai ◽  
...  
Keyword(s):  
Parent Compound ◽  
Amyloid Plaques ◽  
Enol Form ◽  
19F Nmr ◽  
Enolic Form ◽  
Curcumin Derivatives ◽  
Alkyl Groups ◽  
Alzheimer Brain ◽  
Hydrolysis Of ◽  
Related Compounds

1,7-Bis(4′-hydroxy-3′-trifluoromethoxyphenyl)-1,6-heptadiene-3,5-dione (2a), related to curcumin, and thirteen 4-substituted derivatives were prepared and their keto/enol ratio in DMSO[D6] was determined by 19F NMR because the enolic form of these related curcumins had been shown to bind to amyloid plaques in the Alzheimer brain. The parent compound and the 4-ethoxycarbonyl derivative were almost 100 % in the enolic form that contains a conjugated hepta-1,4,6-trien-3-on-5-ol backbone. Enolisation decreased to varying amounts in the derivatives that had 4-substituted alkyl groups. Attempts to prepare the 4-hydroxypropyl derivative by hydrolysis of O-methoxymethyl 2m or O-tetrahydropyranyloxy 2n protected derivatives led to cyclised products. A related pyrimidine compound 6b that mimicked a fixed enol form was also prepared.

Synthesis of 5-n-alkylresorcinol dimethyl ethers and related compounds via substituted thiophens

1971 ◽  
Vol 24 (12) ◽  
pp. 2655 ◽  
Author(s):  
D Buddhasukh ◽  
JR Cannon ◽  
BW Metcalf ◽  
AJ Power
Keyword(s):  
Raney Nickel ◽  
Stannic Chloride ◽  
Electrophilic Attack ◽  
Related Compounds ◽  
By Products

5-n-Alkylresorcinol dimethyl ethers have been synthesized by desulphurization of 2-(3,5-dimethoxybenzyl)-5-n-alkylthiophens with Raney nickel. The method has been adapted to the preparation of 9-(3,6- dimethoxyphenyl)nonyl alcohol which has been converted into both (2)- and (E)-15-(3,5-dimethoxyphenyl)pentadec-5-ene. ��� Friedel-Crafts acylation of 2-(3,5-dimethoxybenzyl)thiophen with n- hexoyl chloride, or with n-decoyl chloride, in the presence of stannic chloride, yielded the expected 2-(3,6-dimethoxybenzyl)-5-n- acylthiophens, but by-products were formed as the result of competing electrophilic attack on the 3,5-dimethoxybenzyl moiety. The chief by- products, which arise by subsequent Bradsher cyclodehydration, have been formulated as 5,7-dimethoxy-4-n-alkylnaphtho[2,3-b]thiophens. ��� An attempt to synthesize 1,14-bis(3,5-dimethoxyphenyl)tetradecane from 2,2?,6?,2?-terthienyl by an adaptation of this method was unsuccessful.

scholarly journals Nutritional regime of gray forest soil аt different anthropogenic loads

2020 ◽  
pp. 16-26
Author(s):  
N. Borys ◽  
L. Krasjuk
Keyword(s):  
Forest Soil ◽  
Crop Rotation ◽  
Main Product ◽  
Gray Forest Soil ◽  
Organic Fertilizer ◽  
Soil Layer ◽  
Soil Nutrient ◽  
Mineral Fertilizers ◽  
Nutrient Regime ◽  
By Products

The aim of the research is to establish the peculiarities of the formation of the nutrient regime of gray forest soil with different systems of basic cultivation, fertilization and sealing of by-products of crops in short-rotation 4-field grain crop rotation – winter wheat–corn for grain–barley–soybean. Evaluate the quantitative inflow of biomass, participation in the formation of the nutrient regime of gray forest soil, especially the differentiation of 0–40 cm of soil layer depending on the distribution of nutrients in different tillage soil systems. The studies were carried out in a long-term stationary experiment of the department of soil cultivation and weed control of the NSC «Institute of Agriculture of the NAAS», founded in 1969. The fertilization system consisted of the application of mineral fertilizers N65Р58К68 kg acting things per 1 ha of crop rotation area. As an organic fertilizer, we used by-products of crop rotation, where during 2009–2013 received an average of 5,17–5,50 t/ha, and 2014–2017 – 6,65–7,76 t/ha of crop rotation. The existing yield of the main product significantly influenced the volume of the non-commodity part, with the growth of the main product, the growth of by-products also took place in direct proportion. Nitrogen removal averaged 105 kg/ha, and with biomass it returned on average 55,4 kg/ ha, nitrogen with a full mineralization cycle, in general, this corresponds to 45–47 % of the share of costs. In general, the return of phosphorus from by-products for the rotation of 5 received an average of 12,0–16,7 kg/ha and 4-field crop 26 rotation 19,5–22,0 kg/ha, which was 35–40 % of the total removal harvest. The soil received many times more potassium from the biomass of agricultural crops than part of the cost of the main product, due to the attraction of the maize leaf mass, from which an average of 177–253 kg/ha enters the soil, and for crop rotation – 61,4–95,4 kg/ha per hectare of sown area. Key words: gray forest soil, soil nutrient regime, recycling of nutrients, main and by-products of crops.

FTIR as a rapid tool for monitoring molecular weight distribution during enzymatic protein hydrolysis of food processing by-products

2017 ◽  
Vol 9 (29) ◽  
pp. 4247-4254 ◽  
Author(s):  
Sileshi Gizachew Wubshet ◽  
Ingrid Måge ◽  
Ulrike Böcker ◽  
Diana Lindberg ◽  
Svein Halvor Knutsen ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Molecular Weight Distribution ◽  
Weight Distribution ◽  
Food Processing ◽  
Protein Hydrolysis ◽  
Multivariate Approach ◽  
Hydrolysis Of ◽  
By Products ◽  
Rapid Tool

An FTIR-based multivariate approach is developed for monitoring molecular weight distribution during enzymatic protein hydrolysis of byproducts.

scholarly journals Identification of a Key Enzyme for the Hydrolysis of β-(1→3)-Xylosyl Linkage in Red Alga Dulse Xylooligosaccharide from Bifidobacterium Adolescentis

Marine Drugs ◽  
2020 ◽  
Vol 18 (3) ◽  
pp. 174 ◽  
Author(s):  
Manami Kobayashi ◽  
Yuya Kumagai ◽  
Yohei Yamamoto ◽  
Hajime Yasui ◽  
Hideki Kishimura
Keyword(s):  
Main Product ◽  
Specific Activity ◽  
Red Alga ◽  
Glycoside Hydrolase Family ◽  
Bifidobacterium Adolescentis ◽  
Glycoside Hydrolase Family 43 ◽  
Key Enzyme ◽  
Hydrolysis Of ◽  
Low Activity ◽  
Hydrolase Family

Red alga dulse possesses a unique xylan, which is composed of a linear β-(1→3)/β-(1→4)-xylosyl linkage. We previously prepared characteristic xylooligosaccharide (DX3, (β-(1→3)-xylosyl-xylobiose)) from dulse. In this study, we evaluated the prebiotic effect of DX3 on enteric bacterium. Although DX3 was utilized by Bacteroides sp. and Bifidobacterium adolescentis, Bacteroides Ksp. grew slowly as compared with β-(1→4)-xylotriose (X3) but B. adolescentis grew similar to X3. Therefore, we aimed to find the key DX3 hydrolysis enzymes in B. adolescentis. From bioinformatics analysis, two enzymes from the glycoside hydrolase family 43 (BAD0423: subfamily 12 and BAD0428: subfamily 11) were selected and expressed in Escherichia coli. BAD0423 hydrolyzed β-(1→3)-xylosyl linkage in DX3 with the specific activity of 2988 mU/mg producing xylose (X1) and xylobiose (X2), and showed low activity on X2 and X3. BAD0428 showed high activity on X2 and X3 producing X1, and the activity of BAD0428 on DX3 was 1298 mU/mg producing X1. Cooperative hydrolysis of DX3 was found in the combination of BAD0423 and BAD0428 producing X1 as the main product. From enzymatic character, hydrolysis of X3 was completed by one enzyme BAD0428, whereas hydrolysis of DX3 needed more than two enzymes.

Utilization of Silica from Indonesian Solid Wastes as Catalyst Materials

2020 ◽  
Vol 849 ◽  
pp. 72-77
Author(s):  
Firman Kurniawansyah ◽  
Amila D. Istiqomah ◽  
Aisyah J. Malahayati ◽  
Himawan Tri Bayu Murti Petrus ◽  
Achmad Roesyadi
Keyword(s):  
Acidic Solution ◽  
Agricultural Waste ◽  
Sulphuric Acid Solution ◽  
Solid Catalyst ◽  
Glucose Yield ◽  
Active Metal ◽  
Alternative Sources ◽  
Hydrolysis Of ◽  
Seaweed Industry ◽  
By Products

Synthesizing materials can be attempted by utilizing alternative sources such as wastes or disposed/by-products of certain activities. In this article, exploration of silica from agricultural waste and from geothermal sludgefor production of silica catalysts, are presented. The first silica catalyst was synthesized from rice husk. The husk was initially heated until silica ashes could be formed. After immersion in acidic solution, impregnation with nickel and molybdenum were conducted to introduce active metal of nickel (Ni) and molybdenum (Mo) in the support structure. The catalyst formed, Ni-Mo/SiO2 was applied to convert crude palm oil into biofuels. The other silica catalyst was obtained from geothermal sludge. After washing, the catalyst was soaked in sulphuric acid solution to form acidic silica solid catalyst. The catalyst was applied in hydrolysis of seaweed-industry solid waste to produce glucose. The catalyst was relatively successful to facilitate 19-20% glucose yield, or up to 21% glucose selectivity from waste material.

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