cas 5455-98-1, N-(2,3-EPOXYPROPYL)PHTHALIMIDE

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Synthesis of α-phthalimido-α′-dithiocarbamato propan-2-ols via a one-pot, three-component epoxide ring-opening in water
Regioselective ring-opening of the N-(2,3-epoxypropyl)phthalimide with in situ prepared dithiocarbamic acid in water is reported for the synthesis of a new family of α-phthalimido-α′-dithiocarbamato propan-2-ols. The present method is simple, EtOAc is used for work-ups and affords excellent yield of products.
Halimehjani, Azim Ziyaei,Hooshmand, Seyyed Emad,Shamiri, Elham Vali
p. 5454 - 5457
(2014)
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Titus et al.
p. 39,61
(1948)
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Poly(glycidyl amine) and copolymers with glycidol and glycidyl amine repeating units: Synthesis and characterization
The synthesis and characterization of poly(glycidol-co-glycidyl amine), poly(glycidol)-block-poly(glycidyl amine), and poly(glycidol) end-capped with a glycidyl amine unit is reported. Copolymerization of ethoxyethyl glycidyl ether with epichlorohydrin using tetraoctylammonium bromide/triisobutylaluminium as catalyst leads to statistical or block copolymers. Sequential addition of the monomers to the initiator leads to block copolymers while simultaneous copolymerization of the monomers results in statistical copolymers. The resulting polyethers with protected hydroxymethyl and chloromethyl side groups were converted in three steps to poly(epoxide)s with hydroxymethyl and aminomethyl side chains. These polymers have a high potential for the preparation of multifunctional polymers since amine and alcohol groups can be addressed selectively by electrophiles. An intermediate in the synthesis of these functional poly(epoxide)s are polyethers with hydroxymethyl and azidomethyl side chains. The azide group of these copolymers was further functionalized via a click reaction with propargyl alcohol proving the reactivity of the polymer bound azide group. Furthermore, preparation of poly(glycidol)s bearing a glycidyl amine end group is reported.
Meyer, Joerg,Keul, Helmut,Moeller, Martin
p. 4082 - 4091
(2011)
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COMPOUNDS FOR PREVENTING MIGRATION OF CANCER CELLS
The present invention relates to a composition for use in preventing migration of cancer cells in a subject known or suspected to suffer from cancer, the composition comprising at least one metal complex having the structure (I), formula (I), wherein M is a metal, preferably selected from the group consisting of copper, iron, manganese and zinc, X is Xa or Xb, wherein Xa is selected from the group consisting of O, S and -N(R1)-, wherein R1 is H or alkyl, and wherein Xb is a group forming a coordinate covalent bond to a second metal M', preferably a group O, S or -N(R1)-, wherein M' is preferably selected from the group consisting of copper, iron, manganese and zinc, and wherein M' and M may be the same or different and are preferably the same, Z1 and Z2, are independently of each other a, substituted or unsubstituted, -Aryl-O-, -Aryl-N- or heteroaryl group, Y is Ya or Yb, wherein Ya is selected from the group consisting of H, alkyl, -OH, -SH, halogen, and -NR3R4, wherein R3 and R4, are independently of each other selected from H and alkyl, preferably R3 and R4 are both H, and wherein Yb is a group forming a coordinate covalent bond to M or M', preferably Yb is a group O, S or -N(RYb1RYb2), wherein RYb1 and RYb1, are, independently of each other, H or alkyl, preferably H, and wherein n and m are integers, which are independently of each other, 0 or 1, Y2 is water or a halogen, and wherein Y3 is water or a halogen. The present invention further relates to a combined preparation comprising the aforesaid composition as well as to an in vitro method, for determining whether cancer cells are susceptible to immobilizing by the aforesaid compound.
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Page/Page column 62; 64

(2021/04/10)

A 5 - aminolevulinic acid hydrochloride of new synthetic method (by machine translation)
The invention belongs to the field of organic synthesis, in particular relates to a 5 - aminolevulinic acid hydrochloride new synthesis method. The synthesis method the new synthesis method ech as the starting material, by Gabriel reaction, ring-opening, oxidation, substituted, hydrolysis reaction steps such as to obtain the target product 5 - aminolevulinic acid hydrochloride. The invention uses a 5 - aminolevulinic acid hydrochloride new synthesis method, can significantly speed up the reaction rate and to improve the yield, while at the same time little side reaction, the operation is simple, after treatment is convenient, and is suitable for industrial production. (by machine translation)
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Paragraph 0009-0010

(2019/05/16)

SUBSTITUTED 1,1'-BIPHENYL COMPOUNDS, ANALOGUES THEREOF, AND METHODS USING SAME
The present invention includes substituted 3,3'-bis(phenoxymethyl)-1,1'-biphenyl compounds, analogues thereof, and compositions comprising the same, that can be used to treat or prevent hepatitis B virus (HBV) and/or hepatitis D virus (HDV) infections in a patient.
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Page/Page column 93

(2019/10/23)

Citric acid mosapride intermediate product and application
The invention belongs to the field of medical chemistry synthesis, and provides a preparation method of citric acid mosapride intermediate product IV 4-[(4-fluorophenyl)methyl]-2-morpholinemethanaminesalt and citric acid mosapride. The 2-(4-fluorobenzoamido)ethanol and 1H-Isoindole-1,3(2H)-dione,2-(2-oxiranylmethyl) are taken as raw materials, and the intermediate product IV 4-[(4-fluorophenyl)methyl]-2-morpholinemethanamine salt is obtained after acid treating is conducted; the intermediate product IV and an intermediate V 2-oxethyl-4-acetamido-5-Chlorobenzoic acid ethyl ester compounds aretaken as raw materials, dichloromethane is taken as a solvent, and EDCI and DMAP are taken as catalysts to prepare mosapride salt; the mosapride salt is reacted with citric acid aqueous solution to prepare citric acid mosapride. The intermediate product has the advantages that products are high in yield, raw materials are easy to obtain, the production cost is low, and the intermediate product issuitable for industrialized production.
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Paragraph 0041; 0042

(2018/09/08)

Design, synthesis, and biological evaluation of 2-(benzylamino-2-hydroxyalkyl)isoindoline-1,3-diones derivatives as potential disease-modifying multifunctional anti-Alzheimer agents
The complex nature of Alzheimer's disease calls for multidirectional treatment. Consequently, the search for multi-target-directed ligands may lead to potential drug candidates. The aim of the present study is to seek multifunctional compounds with expected activity against disease-modifying and symptomatic targets. A series of 15 drug-like various substituted derivatives of 2-(benzylamino-2-hydroxyalkyl)isoindoline-1,3-diones was designed by modification of cholinesterase inhibitors toward β-secretase inhibition. All target compounds have been synthesized and tested against eel acetylcholinesterase (eeAChE), equine serum butyrylcholinesterase (eqBuChE), human β-secretase (hBACE-1), and β-amyloid (Aβ-aggregation). The most promising compound, 12 (2-(5-(benzylamino)-4-hydroxypentyl)isoindoline-1,3-dione), displayed inhibitory potency against eeAChE (IC50 = 3.33 μM), hBACE-1 (43.7% at 50 μM), and Aβ-aggregation (24.9% at 10 μM). Molecular modeling studies have revealed possible interaction of compound 12 with the active sites of both enzymes-acetylcholinesterase and β-secretase. In conclusion: modifications of acetylcholinesterase inhibitors led to the discovery of a multipotent anti-Alzheimer's agent, with moderate and balanced potency, capable of inhibiting acetylcholinesterase, a symptomatic target, and disease-modifying targets: β-secretase and Aβ-aggregation.
Panek, Dawid,Wi?ckowska, Anna,Pasieka, Anna,Godyń, Justyna,Jończyk, Jakub,Bajda, Marek,Knez, Damijan,Gobec, Stanislav,Malawska, Barbara
(2018/02/14)

Method for preparing mosapride citrate intermediate
The invention belongs to the technical field of medicines and particularly relates to a method for preparing a mosapride citrate intermediate IV 4-(4-fluorophenyl)-2-aminomethyl morpholine. The methodcomprises the following steps: phthalimide potassium salt and dichloro-2-propanol react to produce an intermediate II N-(2-hydroxy-3-chloropropyl) phthalimide, then the produced intermediate II and an intermediate I 2-(4-fluorphenylamine)ethyl alcohol are condensed to prepare an intermediate III N-3-[4-fluorophenyl-2-(hydroxy-ethylamine)-2-hydroxypropyl]phthalic diamide, and the intermediate IIIis subjected to cyclization and hydrolysis to obtain the intermediate IV 4-(4-fluorophenyl)-2-aminomethyl morpholine. The method is short in route, lower in production cost and suitable for industrialproduction.
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Paragraph 0050; 0051; 0052

(2018/07/06)

A practical and enantiospecific synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ols
A highly enantiospecific, azide-free synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ol in excellent yield was developed. The key step of the synthesis involves the enantiospecific ring openings of enantiomerically pure (R)- and (S)-2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-diones with the diethyl malonate anion and subsequent decarboxylation.
Babu, Meruva Suresh,Raghunadh, Akula,Ramulu, Konda,Dahanukar, Vilas H.,Syam Kumar, Unniaran K.,Dubey, P. Kumar
p. 1507 - 1515
(2015/02/19)

Highly regioselective and efficient synthesis of aminoepoxides by ring closure of aminohalohydrins mediated by KF-Celite
The regioselective synthesis of several aminoepoxides has been achieved without observing any trace of azetidinols, which are usually reported as the exclusive reaction products when aminohalohydrins are treated with bases. The use of the mild supported base KF-Celite in refluxing acetonitrile is crucial for modulating the excellent regioselectivity observed. Georg Thieme Verlag Stuttgart . New York.
Pace, Vittorio,Hoyos, Pilar,Sinisterra, José Vicente,Alcántara, Andrés R.,Holzer, Wolfgang
supporting information; experimental part
p. 1831 - 1834
(2011/09/16)

2-Methyltetrahydrofuran as a suitable green solvent for phthalimide functionalization promoted by supported KF
An efficient chemoselective nitrogen functionalization of phthalimides by using KF-Alumina in 2-methyltetrahydrofuran, a solvent obtained from renewal sources, is described.
Pace, Vittorio,Hoyos, Pilar,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.
supporting information; experimental part
p. 1380 - 1382
(2010/09/05)

Novel series of highly potent non-peptide growth hormone secretagogues with improved bioavailability
The discovery and the SAR of acylproline derivatives as highly potent growth hormone secretagogues (GHSs) with good oral bioavailability are described. One representative compound, N-[3-(2,2-dimethylpropylamino)-2-hydroxypropyl]-2(R)-[1-(2,2-dimethylpropionyl)pyrrolidine-2(S)- carbonylamino]-3-naphthalen-2-ylpropionamide (4e), showed potent GHS activity (ED50=1 nM) and good oral bioavailability (BA=33.2%). Moreover, the optically pure N-[3-(2,2-dimethylpropylamino)-2(S)-hydroypropyl]-2(R)-[1-(2,2-dimethylpropionyl)pyrrolidine-2(S)-carbonylamino]-3-naphthalen-2- ylpropionamide ((2S)-4e) showed a good metabolic stability against in vitro clearance (human liver microsome) with potent GHS activity.
Ishige, Hirohide,Ishiyama, Nobuo,Mimura, Mitsuo,Hayashida, Mitsuo,Okuno, Tadashi,Ukai, Kiyoharu,Kiyofuji, Takeshi,Yoneda, Yasuo,Tauchi, Shinji,Aoyama, Akinori,Inoguchi, Kiyoshi
p. 561 - 566
(2007/10/03)

A facile synthesis of 2-((5R)-2-oxo-5-oxazolidinyl)methyl-1H-isoindole-1, 3(2H)-dione
Synthesis of enantiomerically pure 2-((5A)-2-oxo-5-oxazolidinyl) methyl)-1H-isoindole-1,3(2H)-dione, a key precursor in the preparation of oxazolidinone class of antibacterial agents starting from (S)-epichlorohydrin has been achieved.
Madhusudhan,Ready, G. Om,Ramanatham,Dubey
p. 1264 - 1268
(2007/10/03)

Urea derivatives as inhibitors for CCR-3 receptor
Urea and thiourea derivatives inhibit cell function of the chemokine receptor CCR-3. These compounds offer an effective means for treating a range of diseases thought to be mediated by the CCR-3 receptor. A variety of useful urea and thiourea derivatives can be synthesized using liquid and solid phase synthesis protocols.
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Page/Page column 26; 203-204

(2010/02/11)

Organic reactions in ionic liquids: N-alkylation of cyclic imides with alkyl halides promoted by potassium fluoride
An ionic liquid based on 1-butyl-3-methylimidazolium hexafluorophosphate is used as an efficient reusable reaction medium in the N-alkylation of cyclic imides with alkyl halides promoted by fluoride ion.
Hu, Yi,Chen, Zhen-Chu,Le, Zhang-Gao,Zheng, Qin-Guo
p. 276 - 278
(2007/10/03)

Synthesis of novel cationic lipids: Effect of structural modification on the efficiency of gene transfer
A series of novel cationic lipids was designed and synthesized in an effort to understand the importance of the various structural features with respect to transfection efficiency. Particular attention has been paid to the hydrophobic domain and the cationic headgroup. An efficient method of synthesizing asymmetric diether lipids is described, using alkyl chains ranging from C12 to C18 and the unsaturated oleyl group. The ternary formulations including the diether lipid 3β-[N-(N′,N′-dimethylaminoethyl)carbamoyl]cholesterol (DC-Chol) and dioleoyl phosphatidylethanolamine (DOPE) were up to 10-fold more efficacious in in vitro assays than the DC-Chol/DOPE control. The shorter and most asymmetric diether lipids performed the best. The chemical nature and basicity of the headgroups have been varied by the coupling of the four naturally occurring amino acids with cationic side chains-arginine, histidine, lysine, and tryptophan. Transfection efficiency was highest for arginine/lysine derivatives, with binary formulations containing the amino acid derivative alone and DOPE proving superior.
Heyes,Niculescu-Duvaz,Cooper,Springer
p. 99 - 114
(2007/10/03)

Phthalamide compounds
The present invention includes a number of novel intermediates such as the (S)-secondary alcohol of formula (VIIIA) X2—CH2—C*H(OH)—CH2—NH—CO—RN??(VIIIA) and processes for production of pharmacologically useful oxazolidinones.
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Page column 18

(2010/11/29)

Synthesis of a series of sulfinic acid analogs of GABA and evaluation of their GABA(B) receptor affinities
A series of γ-aminobutyric acid (GABA) 1 analogs was prepared in which the carboxylic acid group of GABA was replaced with a sulfinic acid group and their affinity for the GABA(B) receptor investigated.
Carruthers, Nicholas I.,Spitler, James M.,Wong, Shing-Chun,Blythin, David J.,Chen, Xiao,Shue, Ho-Jane,She, Hoyan S.,Lee, Joe F.,Rizzo, Charles,Ting, Pauline C.,West Jr., Robert E.
p. 3059 - 3064
(2007/10/03)

Studies on quinazolines IX:1 Fluorination versus 1,2-migration in the reaction of 1,3-bifunctionalized amino-2-propanol with DAST
Treatment of 1-phthaloylamino-3-[4-(2-methoxyphenyl)piperazin-1-yl]- propanol (7) with DAST induced 1,2-migration via a proposed spiro-aziridinium intermediate to give N-[2-fluoro-3-[4-(2-methoxyphenyl)piperazin-1- yl]propyl]-phthalimide (11a) in 13% yield and N-12-fluoromethyl-2-[4-(2- methoxyphenyl)-piperazin-1-yl]ethyl]phthalimide (11b) in 73% yield.
Chern, Ji-Wang,Chang, Jun-Yi,Usifoh, Cyril O.,Gutsait, Alexander
p. 8483 - 8486
(2007/10/03)

Regioselectivity of the ring opening of propene oxides bearing electron-withdrawing substituents at the methyl group with Olah's reagent
The regiochemistry of the hydrofluorination of terminal epoxides with Olah's reagent (Py·9HF) is dependent on the electron-withdrawing character of the β-substituents. Phenoxy ethers with different substitution patterns of the aromatic ring and several N-heterocycles were examined as β-substituents.
Skupin, Rolf,Haufe, Guenter
p. 157 - 165
(2007/10/03)

N-[(1,4-DIAZABICYCLO[2.2.2] OCT-2-YL)METHYL] BENZAMIDE DERIVATIVES, THEIR PREPARATIONS AND THEIR APPLICATION IN THERAPEUTICS
An optically active isomer or a racemate of a compound of general formula (I) STR1 in which either R 1 represents a methoxy or cyclopropylmethoxy group andR 2 represents a hydrogen, chlorine or bromine atom, orR 1 and R 2 together form, and in this order, a group of formula--O--CH 2--O--,--O--(CH 2) 2--,--O--(CH 2) 2--O--or--O--(CH 2) 3--O--,R 3 represents a hydrogen atom or an amino group, andR 4 represents a hydrogen, chlorine or bromine atom,in the form of a free base or of a pharmaceutically acceptable acid addition salt.
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(2008/06/13)

Synthesis, characterization, and reversible oxygenation of μ-alkoxo diiron(II) complexes with the dinucleating ligand N,N,N?,N?-tetrakis{(6-methyl-2-pyridyl)methyl}-1,3-diaminopropan-2- olate
Two new types of dinucleating ligands, symmetric Me4-tpdp and asymmetric Me2-tpdp, were synthesized (Me4-tpdp = N,N,?,?-tetrakis{(6-methyl-2-pyridyl)methyl}-1,3-diaminopropan-2- olate and Me2-tpdp = N,N-bis{(6-methyl-2-pyridyl)methyl}-?,?-bis(2-pyridylmethyl)-1,3- diaminopropan-2-olate). Their μ-alkoxo diiron(II) complexes [Fe2(Me4-tpdp)(C6H5COO)(H 2O)](BF4)2 (1), [Fe2(Me4-tpdp)(CF3CO2)(H 2O)2](BF4)2·H2O (2), and [Fe2(Me2-tpdp)(CF3CO2)](BF 4)2·nH2O (3) were synthesized, and the structure of complex 1 was determined by X-ray crystallography. Complex 1 crystallizes in the monoclinic space group P2i/n with a = 19.257(2) ?, b = 17.166(3) ?, c = 12.558(2) ?, β= 96.55(1)○, and Z = 4. The complex has a doubly bridged structure with a μ-alkoxo of Me4-tpdp and μ-benzoate and contains two distinct iron centers: one five-coordinate iron center with an N3O2 donor set and one six-coordinate iron center with an N3O3 donor set with an additional coordinated water molecule. Introduction of a 6-methyl group in the pyridyl group results in elongation of the Fe-N(pyridyl) bond distances. The Fe-N and Fe-O bond distances in the six-coordinate iron center are substantially longer than those in the five-coordinate iron center except for the Fe-N(tertiary amine) bonds. The M?ssbauer spectrum of 1 exhibited two sets of quadrupole doublets corresponding to the two distinct iron centers. The electronic spectra of 1 revealed that dissociation of the coordinated water occurs in CH2Cl2 to form two five-coordinate iron centers, whereas in DMSO, six-coordinate iron centers are predominant due to the coordination of DMSO. Complexes 1 and 2 showed reversible oxygenation at -40 °C, whereas reversible oxygenation was not observed for complex 3. The thermal stability of the oxy complexes toward irreversible oxidation is highly dependent on the relative degree of steric bulkiness of the dinucleating ligands and their electron donor ability; introduction of the 6-methyl group in the pyridyl group stabilizes the oxy form toward irreversible oxidation. The resonance Raman spectrum of the oxy-1 exhibited two oxygenisotope sensitive bands in the v(O-O) region and two bands in the v(Fe-O) region. The presence of the two v(O-O) Raman bands at 918 and 891 cm-1 is interpreted in terms of Fermi resonance, while the two v(Fe-O) bands are assigned to the symmetric and antisymmetric combinations of Fe-O stretchings of the Fe-O-O-Fe unit. Thus the Raman spectra indicated the formation of the μ-peroxo species. The oxygen affinities (P1/2) of the complexes were determined for the first time by spectrophotometric methods; those of 1 and 2 in CH2Cl2 at -40 °C are ca. 6 and ca. 41 Torr, respectively.
Hayashi, Yoshihito,Kayatani, Takayuki,Sugimoto, Hideki,Suzuki, Masatatsu,Inomata, Katsuhiko,Uehara, Akira,Mizutani, Yasuhisa,Kitagawa, Teizo,Maeda, Yonezo
p. 11220 - 11229
(2007/10/03)

The syntheses of purine and pyrimidine secoribo-nucleosides: Acyclo-uridine derivative of cyclophosphamide
The synthesis of secoribo-nucleoside analogues is described. Compounds 4 and 5 possess interesting antiviral effects in vitro. A procedure is also developed for the conversion of acyclo-uridine nucleoside 7 to a novel derivative of cyclophosphamide 8.
Zakerinia,Davary,Hakimelahi
p. 912 - 915
(2007/10/02)

Synthesis of aminomethyl and amino analogs of 5-benzylacyclouridine and 5-benzyloxybenzylacyclouridine
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Chu,Chen,Weng,et al.
p. 989 - 995
(2007/10/02)

Propan-2-ol derivatives, a process for their production and medicaments containing these compounds
The invention relates to new propan-2-ol derivatives corresponding to the following general formula STR1 in which R represents STR2 and to salts thereof with pharmacologically acceptable acids. These compounds have a selective effect on histamine-H2 -receptors.
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(2008/06/13)