Syntheses of Liquid Crystal Intermediates 4-Alkylbenzenethiols and Phenols

Neubert, Mary E.; Laskos, S. J.; Griffith, R. F.; Stahl, Marion; Maurer, L. J.

doi:10.1080/00268947908084856

Cited by 18 publications

(4 citation statements)

References 14 publications

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“…In each case, the sulfonamide group interacts with Arg23, Arg25, and Lys14 in a manner similar to the best pose exhibited by compound 1 . 28 Compounds 2–7 and 8–16 bear amino and acetamido groups at R 4 , respectively, and variable substitution at R 1 . For the most part, these modifications did not result in large changes in the GOLD docking scores (see Table 2).…”

Section: Resultsmentioning

confidence: 99%

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Development of sulfonamide AKT PH domain inhibitors

Ahad

Zhang

Du-Cuny

et al. 2011

Bioorganic & Medicinal Chemistry

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Disruption of the phosphatidylinositol 3-kinase/AKT signaling pathway can lead to apoptosis in cancer cells. Previously we identified a lead sulfonamide that selectively bound to the pleckstrin homology (PH) domain of AKT and induced apoptosis when present at low micromolar concentrations. To examine the effects of structural modification, a set of sulfonamides related to the lead compound was designed, synthesized, and tested for binding to the expressed PH domain of AKT using a surface plasmon resonance-based competitive binding assay. Cellular activity was determined by means of an assay for pAKT production and a cell killing assay using BxPC3 cells. The most active compounds in the set are lipophilic and possess an aliphatic chain of the proper length. Results were interpreted with the aid of computational modeling. This paper represents the first structure-activity relationship (SAR) study of a large family of AKT PH domain inhibitors. Information obtained will be used in the design of the next generation of inhibitors of AKT PH domain function.

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Section: Resultsmentioning

confidence: 99%

“…28 The mixture was stirred at rt for 20 h. The mixture was poured on ice (200 mL) and extracted with EtOAc (3 × 100 mL). The combined extracts were washed with water, aqueous NaHCO 3 , and water, dried over anhydrous Na 2 SO 4 , and concentrated in vacuo.…”

Section: Methodsmentioning

confidence: 99%

Development of sulfonamide AKT PH domain inhibitors

Ahad

Zhang

Du-Cuny

et al. 2011

Bioorganic & Medicinal Chemistry

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“…The following intermediates were synthesized using previously described methods: 4-benzyloxybenoic acid [32], 4-alkylbenzoic acids and acid chlorides [33], 4-alkylphenols [34], 4-(keto)benzoic acids [35], 4-hexyloxyphenol [36], 4-(ester)phenols [17] and 2-F-4-decyloxybenzoic acid [28]. Anhydrous reactions were run in flame-dried glassware using solvents dried over Linde #4A molecular sieves.…”

Section: Synthesismentioning

confidence: 99%

The effect of fluorinated terminal chains on the mesomorphic properties of 4,4′‐disubstituted phenyl benzoates

et al. 2005

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A variety of 4,49-disubstituted phenyl benzoates having a terminal chain containing multifluorine atoms, attached directly to the benzene ring or through an ester group, have been synthesized and their mesomorphic properties determined by hot stage polarizing optical microscopy. These properties were compared to those of the corresponding hydrogenated esters and to other esters containing rigid terminal chains. Usually transition temperatures were higher and mesophase ranges wider than those observed for the parent compounds but no nematic phases were found. Any mesophase seen was usually a smectic A phase sometimes accompanied by a smectic C phase. Crystal E phases were found along with the smectic A phase in alkyl or alkoxy esters having a C 9 F 19 CO 2 chain on the acid side. A first order smectic A-smectic C transition was observed in the ester with CN on the acid side and O 2 CC 7 F 15 on the phenol side. A comparison of the effect of a terminal fluorinated chain and a lateral fluorine group on one set of esters is also included.

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“…The phenols 19 (n51, Y5R) [34], RO [35], CO 2 R[4], COR [1], OCO 2 R [2]; thiols 20 (Y5R) [33], RO [36] and acids 26 (n51, X5R) [24] were prepared using previously published methods. All other starting materials were commercially available and used without purification.…”

Section: Synthesismentioning

confidence: 99%

The effect on mesomorphic properties of a triple bond in a terminal chain of 4,4′‐disubstituted phenyl benzoates and phenyl thiobenzoates

et al. 2005

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2005) The effect on mesomorphic properties of a triple bond in a terminal chain of 4,4′-disubstituted phenyl benzoates and phenyl thiobenzoates, Liquid Crystals, 32:2, 247-266,The effect of a triple bond in a terminal chain on the mesomorphic properties of rod-like mesogens was studied by replacing a straight alkyl chain with a terminal 1,2-alkynyl chain in some esters and thioesters of the type: or by incorporating the triple bond into an alkyl ester chain in esters and thioesters of the types:The triple bond should provide increased rigidity to the triple bond region but increased flexibility at the adjacent single bond. These should have opposite effects on the mesomorphic properties. The first compounds were synthesized by esterification of the appropriate alkynylbenzoic acids with various phenols or thiols using the carbodiimide method. Detailed syntheses are provided for the alkynylbenzoic acids. Preparation of the alkynyl ester compounds was by acylation of the precursor hydroxyl esters or thioesters using either the acid chloride or carbodiimide method. The synthesis of the phenolic or thiolic ester intermediates, usually using a protection group, is described. Mesomorphic properties of these new esters and thioesters were determined using hot stage polarizing microscopy and DSC and compared with those for the known parent compounds. Fewer mesophases having shorter temperature ranges and lower transition temperatures were usually observed. Some of the intermediate phenols or benzyl ethers were also studied. Long chain benzyloxy esters showed a nematic phase as did some of the hydroxy thioesters but no mesophases were observed in the hydroxy esters.

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Syntheses of Liquid Crystal Intermediates 4-Alkylbenzenethiols and Phenols

Cited by 18 publications

References 14 publications

Development of sulfonamide AKT PH domain inhibitors

Development of sulfonamide AKT PH domain inhibitors

The effect of fluorinated terminal chains on the mesomorphic properties of 4,4′‐disubstituted phenyl benzoates

The effect on mesomorphic properties of a triple bond in a terminal chain of 4,4′‐disubstituted phenyl benzoates and phenyl thiobenzoates

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