Synthetic antispasmodics. III. Derivatives of indane-1-carboxylic acid, 1,2,3,4-tetrahydronaphthalene-1-carboxylic acid and indane-1-acetic acid

1951 ◽  
Vol 16 ◽  
pp. 331-343 ◽  
Author(s):  
M. Protiva ◽  
Z. J. Vejdělek ◽  
J. O. Jílek
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Derivatives Of

scholarly journals Conformation and crystal structures of 1-aminocyclohexaneacetic acid (β3,3Ac6c) in N-protected derivatives

2014 ◽  
Vol 70 (11) ◽  
pp. 272-277
Author(s):  
Naiem Ahmad Wani ◽  
Vivek K. Gupta ◽  
Rajni Kant ◽  
Subrayashastry Aravinda ◽  
Rajkishor Rai
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Chair Conformation ◽  
X Ray Diffraction ◽  
Axis Direction ◽  
Centroid Distance ◽  
Ring Centroid ◽  
Ribbon Structures ◽  
Derivatives Of

N-Protected derivatives of 1-aminocyclohexaneacetic acid (β3,3-Ac6c), namely Valeroyl-β3,3-Ac6c-OH [2-(1-pentanamidocyclohexyl)acetic acid, C13H23NO3], (I), Fmoc-β3,3-Ac6c-OH [2-(1-{[(9H-fluoren-9-yloxy)carbonyl]amino}cyclohexyl)acetic acid, C23H25NO4], (II), and Pyr-β3,3-Ac6c-OH {2-[1-(pyrazine-2-amido)cyclohexyl]acetic acid, C13H17N3O3}, (III), were synthesized and their conformational properties were determined by X-ray diffraction analysis. The backbone torsion angles (ϕ, θ) for β3,3-Ac6c-OH are restricted togaucheconformations in all the derivatives, with a chair conformation of the cyclohexane ring. In the crystal structure of (I), the packing of molecules shows both carboxylic acidR22(8) O—H...O and centrosymmetricR22(14) N—H...O hydrogen-bonding interactions, giving rise to chains along thec-axis direction. In (II), centrosymmetric carboxylic acidR22(8) O—H...O dimers are extended through N—H...O hydrogen bonds and together with inter-ring π–π interactions between Fmoc groups [ring centroid distance = 3.786 (2) Å], generate a layered structure lying parallel to (010). In the case of compound (III), carboxylic acid O—H...Npyrazinehydrogen bonds give rise to zigzag ribbon structures extending along thec-axis direction.

scholarly journals Spermine Derivatives of Indole‐3‐carboxylic Acid, Indole‐3‐acetic Acid and Indole‐3‐acrylic Acid as Gram‐Negative Antibiotic Adjuvants

ChemMedChem ◽  
2020 ◽  
Author(s):  
Melissa M. Cadelis ◽  
Steven A. Li ◽  
Marie‐Lise Bourguet‐Kondracki ◽  
Marine Blanchet ◽  
Hana Douafer ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Acrylic Acid ◽  
Gram Negative ◽  
Derivatives Of ◽  
Indole 3 Acetic Acid

Fluorinated tricyclic neuroleptics with prolonged action: 8-Methoxy, 8-ethoxy, 8-ethylthio and 8-hydroxy derivatives of 3-fluoro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1982 ◽  
Vol 47 (5) ◽  
pp. 1382-1391 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Prolonged Action ◽  
Substitution Reactions ◽  
Methoxy Derivative ◽  
Chloro Derivatives ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Central Depressant ◽  
Boiling Toluene

Acids IIa-c were prepared by reactions of (4-fluoro-2-iodophenyl)acetic acid with 4-methoxythiophenol, 4-ethoxythiophenol and 4-(ethylthio)thiophenol and cyclized with polyphosphoric acid in boiling toluene to dibenzo[b,f]thiepin-10(11H)-ones IIIa-c. Reduction with sodium borohydride afforded the alcohols IVa-c which were treated with hydrogen chloride and gave the chloro derivatives Va-c. Substitution reactions with 1-methylpiperazine resulted in the title compounds Ia-c out of which the methoxy derivative Ia was transformed by demethylation with boron tribromide to the phenol Id. Compounds Ia-d are very potent neuroleptics exhibiting a clear prolongation of the central depressant and some prolongation of the cataleptic activity.

scholarly journals Novel Derivatives of 4-Methyl-1,2,3-Thiadiazole-5-Carboxylic Acid Hydrazide: Synthesis, Lipophilicity, and In Vitro Antimicrobial Activity Screening

2021 ◽  
Vol 11 (3) ◽  
pp. 1180
Author(s):  
Kinga Paruch ◽  
Łukasz Popiołek ◽  
Anna Biernasiuk ◽  
Anna Berecka-Rycerz ◽  
Anna Malm ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Carboxylic Acid ◽  
Bacterial Infections ◽  
Acid Hydrazide ◽  
Antimicrobial Effect ◽  
In Vitro Antimicrobial Activity ◽  
Research Goal ◽  
New Compounds ◽  
Derivatives Of

Bacterial infections, especially those caused by strains resistant to commonly used antibiotics and chemotherapeutics, are still a current threat to public health. Therefore, the search for new molecules with potential antimicrobial activity is an important research goal. In this article, we present the synthesis and evaluation of the in vitro antimicrobial activity of a series of 15 new derivatives of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. The potential antimicrobial effect of the new compounds was observed mainly against Gram-positive bacteria. Compound 15, with the 5-nitro-2-furoyl moiety, showed the highest bioactivity: minimum inhibitory concentration (MIC) = 1.95–15.62 µg/mL and minimum bactericidal concentration (MBC)/MIC = 1–4 µg/mL.

ChemInform Abstract: DIHALO DERIVATIVES OF NAPHTHOSTYRIL-N-ACETIC ACID

1978 ◽  
Vol 9 (34) ◽  
Author(s):  
A. P. KARISHIN ◽  
A. A. PECHKA ◽  
N. F. GRINEVA
Keyword(s):  
Acetic Acid ◽  
Derivatives Of

ChemInform Abstract: Anionic Derivatives of Pentafluoro-λ6-sulfanyl (Fluorosulfonyl) Acetic Acid Esters.

ChemInform ◽  
2010 ◽  
Vol 25 (7) ◽  
pp. no-no
Author(s):  
R. WINTER ◽  
G. L. GARD ◽  
R. MEWS ◽  
M. NOLTEMEYER
Keyword(s):  
Acetic Acid ◽  
Derivatives Of ◽  
Acetic Acid Esters ◽  
Acid Esters

The synthesis of norbornanes with functionalized carbon substituents at a bridgehead. 1-(3-Oxonorborn-1-yl)ethanone and 1-(3-oxonorborn-1-yl)-2-propanone

1992 ◽  
Vol 70 (5) ◽  
pp. 1492-1505 ◽  
Author(s):  
Peter Yates ◽  
Magdy Kaldas
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Hydrogen Bromide ◽  
Tertiary Alcohol ◽  
Ethyl Bromoacetate ◽  
Second Molar ◽  
Molar Equivalent ◽  
Acid Lactone ◽  
Basic Hydrolysis ◽  
Hydrolysis Of

Treatment of 2-norobornene-1-carboxylic acid (7) with one equivalent of methyllithium in ether followed by a second molar equivalent after dilution with tetrahydrofuran gave 1-(norborn-2-en-lyl)ethanone (10) and only a trace of the tertiary alcohol 11. Reaction of 7 with formic acid followed by hydrolysis gave a 4:3 mixture of exo-3- and exo-2-hydroxynorbornane-1-carboxylic acid (16 and 17), whereas oxymercuration–demercuration gave only the exo-3-hydroxy isomer 16. Oxidation of 16 and 17 gave 3- and 2-oxonorbornane-1-carboxylic acid (27 and 29), respectively. Oxymercuration–demercuration of 10 gave exclusively 1-(exo-3-hydroxynorborn-1-yl)ethanone (30), which was also prepared by treatment of 16 with methyllithium in analogous fashion to that used for the conversion of 7 to 10. Oxidation of 30 gave 1-(3-oxonorborn-1-yl)ethanone (1). Dehydrobromination of exo-2-bromonorbornane-1-acetic acid and dehydration of 2-hydroxy-norbornane-2-acetic acid derivatives gave 1-(norborn-2-ylidene) acetic acid derivatives to the exclusion of norborn-2-ene-1 -acetic acid derivatives. Treatment of exo-5-acetyloxy-2-norobornanone (52) with ethyl bromoacetate and zinc gave ethyl exo-5-acetyloxy-2-hydroxynorbornane-(exo- and endo-2-acetate (53 and 54). Reaction of 53 with hydrogen bromide gave initially ethyl endo-3-acetyloxy-exo-6-bromonorbornane-1-acetate (59), which was subsequently converted to a mixture of 59 and its exo-3-acetyloxy epimer 61. Catalytic hydrogenation of this mixture gave a mixture of ethyl endo- and exo-3-acetyloxynorbornane-1 -acetate (62 and 63). Basic hydrolysis of this gave a mixture of the corresponding hydroxy acids, 70 and 71; the former was slowly converted to the latter at pH 5. Oxidation of the mixture of 70 and 71 gave 3-oxonorbornane-1-acetic acid (72). Treatment of the mixture with methyllithium as for 16 gave a mixture of 1-(endo- and exo-3-hydroxynorborn-1-yl)-2-propanone (73 and 74), which was oxidized to 1-(3-oxo-norborn-1-yl)-2-propanone (2). Reaction of exo-2-hydroxynorbornane-1-acetic acid lactone (75) with methyllithium in ether gave (1-(exo-2-hydroxynorborn-1-yl)-2-propanone (76), which on oxidation gave the 2-oxo isomer 78 of 2.

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