Cinnamic acid derived oxazolinium ions as novel cytotoxic agents

Hedvati, Lilach; Nudelman, Abraham; Falb, Eliezer; Kraiz, B. O.; Zhuk, R. A.; Sprecher, Milon

doi:10.1016/s0223-5234(02)01375-2

Cited by 17 publications

(10 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The product of synthesis was then extracted by using n-hexane to give 1.62 g of N,N-bis-(2-hydroxyethyl)-pmethoxycinnamamide (2) (20.1 % yield 2H, d, J=8.5 Hz). All of the spectroscopic data are in agreement with those of previously reported (Hedvati et al, 2002;Komala et al, 2017)…”

Section: Amidation Of Epmc (1) To Give Nn-bis-(2hydroxyethyl)-p-methsupporting

confidence: 92%

See 1 more Smart Citation

Direct Amidation of ethyl p-methoxycinnamate to Produce N,N-bis-(2-hydroxyethyl)-p-methoxycinnamamide

Komala

Supandi

Hardiansyah³

2018

JKV

View full text Add to dashboard Cite

Ethyl p-methoxycinnamate (EPMC) (1) is found as a major natural ester in the rhizome of Kaempferia galanga (kencur) and has been known to have various pharmacological activities. The previous study has reported the synthesis of N,N-bis-(2-hydroxyethyl)-p-methoxycinnamamide (2) by using microwave-assisted direct amidation of EPMC (1) with diethanolamine. In this research, we attempt to synthesize of 2 by using a conventional direct amidation of EPMC (1) with diethanolamine. The reaction was conducted without adding any coupling reagents or catalyst. Structure of the synthetic product was determined by using analysis of GC-MS, IR, and 1H-NMR spectroscopic data and then compared to the previously reported.DOI:http://dx.doi.org/10.15408/jkv.v4i1.7300

show abstract

Section: Amidation Of Epmc (1) To Give Nn-bis-(2hydroxyethyl)-p-methsupporting

confidence: 92%

“…Both of these cinnamamides have been reported to have interesting antiinflammatory activity (Komala et al, 2017). In another report, a conventional amidation of cinnamoyl chloride with diethanolamine has also success to obtain compound 2 (Hedvati et al, 2002).…”

Section: Introductionmentioning

confidence: 98%

Direct Amidation of ethyl p-methoxycinnamate to Produce N,N-bis-(2-hydroxyethyl)-p-methoxycinnamamide

Komala

Supandi

Hardiansyah³

2018

JKV

View full text Add to dashboard Cite

show abstract

“…An edge-on arrangement leads to the formation of rodlike entities, especially at higher compressions [15,16]. These arrangements are dependents on the subphase and the particular molecular compound structure [28].…”

Section: Discussionmentioning

confidence: 99%

Characterization of Langmuir and Langmuir–Blodgett films of a thiomacrocyclic ionophore by surface pressure and AFM

Torrent‐Burgués¹,

Pla²,

Escriche³

et al. 2006

Journal of Colloid and Interface Science

View full text Add to dashboard Cite

The new synthesized thiomacrocyclic ionophore 4-phenyl-4-sulfide-11-(1-oxodecyl)-1,7-dithia-11-aza-4-phosphacyclotetradecane has proven to form Langmuir and Langmuir-Blodgett (LB) films. This ionophore shows a large affinity for copper (II) ions. Then, the influence of the subphase composition on the surface pressure-area isotherms has been studied. The LB films have been observed by AFM and the effect of the subphase composition and the deposition surface pressure on the LB films is discussed. AFM image morphology has been correlated to the ionophore molecular structure. Surface pressure-area isotherms and AFM images show that the presence of copper(II) ions has an important role in the film structure.

show abstract

“…In addition to medical applications, it may be a potential functional monomer for photo-responsive materials, such as photo-resists and LSM polymers, due to its two reactive hydroxyls and one light-sensitive cinnamyl group. N-Hydroxyalkyl cinnamamides are often synthesized from cinnamoyl chloride and hydroxyalkylamines [9][10][11][12][13][14]. Narasimhan et al have reported the synthesis of BHECA from cinnamoyl chloride and diethanolamine in ether at room temperature [12], but the selectivity and yield of BHECA in this reaction is quite low.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of N,N-Bis(2-hydroxyethyl) Cinnamamide as a Photo-Responsive Monomer

Jin

Sun

2011

Designed Monomers and Polymers

View full text Add to dashboard Cite

N,N-Bis(2-hydroxyethyl) cinnamamide (BHECA), a diol monomer with a pendant photo-responsive cinnamamide group, was successfully synthesized in high yield from methyl cinnamate (MC) and diethanolamine (DEA) under mild conditions. This ammonolysis approach is characterized by readily available and safe raw material, high yield and easy separation. Also, it does not require the use of an organic solvent. The product was characterized with element analysis, FT-IR, 1 H-NMR, MS, DSC and TGA. Its photo-response was tested by ultraviolet absorption. BHECA is able to undergo reversible [2 + 2] cycloaddition under alternating >260 nm and <260 nm ultraviolet irradiation and, therefore, appears to be a potential functional monomer for synthesis of novel photo-responsive polymers.

show abstract

Cinnamic acid derived oxazolinium ions as novel cytotoxic agents

Cited by 17 publications

References 15 publications

Direct Amidation of ethyl p-methoxycinnamate to Produce N,N-bis-(2-hydroxyethyl)-p-methoxycinnamamide

Direct Amidation of ethyl p-methoxycinnamate to Produce N,N-bis-(2-hydroxyethyl)-p-methoxycinnamamide

Characterization of Langmuir and Langmuir–Blodgett films of a thiomacrocyclic ionophore by surface pressure and AFM

Synthesis and Characterization of N,N-Bis(2-hydroxyethyl) Cinnamamide as a Photo-Responsive Monomer

Contact Info

Product

Resources

About