Electrophilic Trifluoromethylation of Primary Phosphines: Synthesis of aP-Bis(trifluoromethyl) Derivative of BINAP

2010 ◽  
Vol 29 (7) ◽  
pp. 1771-1777 ◽  
Author(s):  
Nicolas Armanino ◽  
Raffael Koller ◽  
Antonio Togni
Keyword(s):  
Trifluoromethyl Derivative

ADMET properties of novel 5-O-benzoylpinostrobin derivatives

2019 ◽  
Vol 30 (6) ◽  
Author(s):  
Mohammad Rizki Fadhil Pratama ◽  
Hadi Poerwono ◽  
Siswandono Siswodiharjo
Keyword(s):  
Androgen Receptor ◽  
Cytotoxic Activity ◽  
Blood Brain Barrier ◽  
Inhibitory Activity ◽  
Water Solubility ◽  
Nitro Derivative ◽  
Total Clearance ◽  
Distribution Parameters ◽  
Trifluoromethyl Derivative ◽  
Class Iv

Abstract Background Prediction of the properties of absorption, distribution, metabolism, excretion, and toxicity (ADMET) from a compound is essential, especially for modified novel compounds. Previous research has successfully designed several modified compounds of 5-O-benzoyl derivatives from pinostrobin, a flavanone that has cytotoxic activity. This study aims to describe the properties of ADMET from the 5-O-benzoylpinostrobin derivative. Methods Prediction of the properties of ADMET was carried out using three web servers consisting of SwissADME, pkCSM, and ProTox-II. The observed parameters are divided into ADMET parameters. Results In general, absorption parameters indicate that the 5-O-benzoylpinostrobin derivative has lower water solubility than the parent pinostrobin. Distribution parameters show mixed results for distribution through the blood-brain barrier. Metabolism parameters showed different results with generally inhibitory activity shown in CYP2C19, CYP2C9, and CYP3A4. The excretion parameters showed a higher total clearance than pinostrobin except in the trifluoromethyl derivative. The toxicity parameters showed both pinostrobin and the 5-O-benzoylpinostrobin derivatives, including the class IV toxicity category with the lowest LD50 value indicated by the nitro derivative of 1500, with the possible target of the androgen receptor and prostaglandin G/H synthase 1. Conclusions Overall, the 5-O-benzoylpinostrobin derivative has the predicted ADMET profile that is relatively similar to pinostrobin, with the most noticeable difference being shown in the absorption parameters where all 5-O-benzoylpinostrobin derivatives have lower water solubility than pinostrobin.

ChemInform Abstract: Farnesyl Chain Modification of Squalene Synthase Inhibitor Benzylfarnesylamine: Conversion to the Terminal Bis(trifluoromethyl) Derivative.

ChemInform ◽  
2010 ◽  
Vol 25 (33) ◽  
pp. no-no
Author(s):  
C. F. JUN. JEWELL ◽  
J. BRINKMAN ◽  
R. C. PETTER ◽  
J. R. WAREING
Keyword(s):  
Squalene Synthase ◽  
Synthase Inhibitor ◽  
Trifluoromethyl Derivative ◽  
Squalene Synthase Inhibitor

A suzuki coupling approach to trifluoromethyl derivative of targretin (LGD 1069)

1997 ◽  
Vol 7 (16) ◽  
pp. 2117-2120 ◽  
Author(s):  
Feng-Ling Qing ◽  
Junfa Fan
Keyword(s):  
Suzuki Coupling ◽  
Coupling Approach ◽  
Trifluoromethyl Derivative

The [4]annulene (cyclobutadiene) system. The tetrakis(trifluoromethyl) derivative

1977 ◽  
Vol 99 (10) ◽  
pp. 3524-3526 ◽  
Author(s):  
Satoru Masamune ◽  
Takahisa Machiguchi ◽  
Matsuhiko Aratani
Keyword(s):  
Trifluoromethyl Derivative

ChemInform Abstract: A Suzuki Coupling Approach to Trifluoromethyl Derivative of Targretin ( LGD 1069).

ChemInform ◽  
2010 ◽  
Vol 28 (50) ◽  
pp. no-no
Author(s):  
F.-L. QING ◽  
J. FAN
Keyword(s):  
Suzuki Coupling ◽  
Coupling Approach ◽  
Trifluoromethyl Derivative

Synthesis of Some 2'-C-Alkyl Derivatives of 9-(2-Phosphonomethoxyethyl)adenine and Related Compounds

1994 ◽  
Vol 59 (9) ◽  
pp. 2069-2094 ◽  
Author(s):  
Hana Dvořáková ◽  
Antonín Holý ◽  
Ivan Rosenberg
Keyword(s):  
Reaction Pathway ◽  
Sodium Hydride ◽  
Amino Group ◽  
Trimethylsilyl Derivative ◽  
Phosphonic Acids ◽  
Alkyl Derivatives ◽  
Hydrolysis Of ◽  
Trifluoromethyl Derivative ◽  
Derivatives Of ◽  
Related Compounds

To study the effect of β-substitution in 2'-alkyl derivatives of 9-(2-phosphonomethoxyethyl)adenine (Ia) on the antiviral activity or group specificity, these derivatives were synthesized. 9-(2-Hydroxyalkyl)adenines VIII were prepared by alkylation of adenine with suitably substituted oxiranes XIII or 2-hydroxyalkyl p-toluenesulfonates IV and VI. After protection of the adenine amino group by benzoylation (compounds IX) or amidine formation (compounds X), the intermediates were alkylated with diisopropyl p-toluenesulfonyloxymethanephosphonate (XI) in the presence of sodium hydride. After deprotection, the obtained phosphonate diesters XII were converted into phosphonic acids I by transsilylation and hydrolysis. This synthetic scheme was used for the preparation of ethyl (Ie), propyl (If), 2-propyl (Ig), 2-methylpropyl (Ih), cyclopropyl (Ii), cyclohexyl (Ij), benzyl (Ik) and phenyl (Il) derivatives. The 2'-trifluoromethyl derivative XXIIa was prepared analogously from 9-(2-hydroxy-3,3,3-trifluoropropyl)adenine (XXa), obtained by alkylation of adenine sodium salt with 2-hydroxy-3,3,3-trifluoropropyl bromide. 2'-Trimethylsilyl derivative XIXa was obtained by alkylation of adenine with 2-diisopropylphosphonomethoxy-3-(4-toluenesulfonyloxy)propyltrimethylsilane (XVII) followed by transsilylation and hydrolysis of diester XVIIIa. 2,6-Diaminopurine derivatives XVIIId and XXIIb were obtained analogously. 9-(3-Phosphonomethoxybutyl)adenine (XXVIII) and 9-(2-methyl-2-phosphonomethoxypropyl)adenine (XXXV) were prepared from the corresponding hydroxy derivatives XXVIb and XXXII, respectively, by the same reaction pathway as derivatives I.

Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: Derivatives of 11H-dibenz[b,f]-1,4-oxathiepin

1982 ◽  
Vol 47 (3) ◽  
pp. 967-983 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
Antonín Dlabač ◽  
Jiřina Metyšová ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Sodium Hydride ◽  
Sulfuryl Chloride ◽  
Side Chains ◽  
Central Ring ◽  
Lithium Compounds ◽  
Psychotropic Agents ◽  
Trifluoromethyl Derivative ◽  
Derivatives Of

Reactions of 2-bromobenzyl bromide and its analogues XVII and XXV with 2-hydroxythiophenol resulted in 11H-dibenz[b,f]-1,4-oxathiepin (Ia) and its 2-chloro (Ib) and 2-trifluoromethyl derivative (IC). Treatment of the lithium compounds derived from Ia and Ib with carbon dioxide and dimethylaminoalkyl chlorides gave compounds IIa, Va and VIab; modification of side chains led to amines IVa, VIIa and VIIIa. 11-(1-Methyl-4-piperidyl) derivatives Xbc were obtained by chlorination of compounds Ibc with sulfuryl chloride or N-chlorosuccinimide and the following treatment with 1-methyl-4-piperidylmagnesium chloride. Compound Ib was transformed by oxidation to the sulfone XX affording by treatment with sodium hydride and tert-aminoalkylchlorides the basic sulfones XXI and XXII. While the nuclearly unsubstituted amines with the aliphatic side chains (IVa and VIIa) have intensive antireserpine activity and are potential antidepressants, the 11-(1-methyl-4-piperidyl) derivatives with a substituent in position 2 of the skeleton (Xbc) are potential neuroleptics; the trifluoromethyl derivative Xc especially has outstanding cataleptic and antiapomorphine efficacy.

Farnesyl chain modification of squalene synthase inhibitor benzylfarnesylamine: Conversion to the terminal bis(trifluoromethyl) derivative

Tetrahedron ◽  
1994 ◽  
Vol 50 (13) ◽  
pp. 3849-3856 ◽  
Author(s):  
Charles F Jewell ◽  
John Brinkman ◽  
Russell C Petter ◽  
James R Wareing
Keyword(s):  
Squalene Synthase ◽  
Synthase Inhibitor ◽  
Trifluoromethyl Derivative ◽  
Squalene Synthase Inhibitor

Isolation and crystal structure of the trifluoromethyl derivative C84(24)(CF3)18 of a minor C84 fullerene isomer

2020 ◽  
Vol 30 (4) ◽  
pp. 474-475
Author(s):  
Nadezhda B. Tamm ◽  
Victor A. Brotsman ◽  
Sergey I. Troyanov
Keyword(s):  
Crystal Structure ◽  
A Minor ◽  
Trifluoromethyl Derivative
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