cas 625-36-5, 3-Chloropropionyl chloride | Articles data

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SYNTHESIS OF 7,7-DIMETHYLBICYCLO-OCTANE BY ACETYLATING A DICOBALTOHEXACARBONYL 4-METHYLPENT-3-EN-1-YNE-1 COMPLEX
Dicobaltohexacarbonyl 4-methyl-pent-3-en-1-yne complexes have been acylated with acryloyl and crotonoyl tetrafluoroborates followed by methanolysis to make acylmethoxy adducts containing hem-dimethyl moieties.Conditions have been defined under which such adducts containing enone systems are selectively reduced to allyl alcohols with retention of the cobaltocarbonyl moieties.The latter can be converted by Quand-Poson reaction to the inaccessible polyfunctional derivatives of 7,7-dimethylbicyclooctane.
Veretenov, A. L.,Gybin, A. S.,Smit, V. A.,Chertkov, V. A.,Shashkov, A. S.
p. 1725 - 1733
(1989)
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Preparation method of 3-chloropropionyl chloride
The invention relates to the technical field of organic synthesis, in particular to a preparation method of 3-chloropropionyl chloride. The preparation method provided by the invention comprises the following steps: 1) introducing hydrogen chloride gas into acrylic acid to carry out addition reaction, and keeping the gas introduction pressure to be less than or equal to 0.15 MPa to obtain a reaction solution; and 2) pumping the reaction liquid in the step 1) into a reaction kettle in vacuum, heating to 30-80 DEG C, dropwise adding thionyl chloride, carrying out negative pressure distillation to 70 DEG C after dropwise adding is finished, and collecting a steamed product at 70-80 DEG C, namely the finished product 3-chloropropionyl chloride. According to the preparation method of the 3-chloropropionyl chloride, the process is simple, the preparation of the 3-chloropropionyl chloride can be realized by adopting extremely simple equipment, the cost is greatly reduced, the total yield (based on acrylic acid) is 90-92%, and the content is greater than or equal to 98.5%.
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Paragraph 0017; 0020-0021; 0024-0025;

(2021/05/08)

Preparation method of 3-chloropropionyl chloride
The invention provides a preparation method of 3-chloropropionyl chloride, wherein the preparation method comprises the following steps: mixing acrylic acid with a certain amount of catalyst, dropwise adding a certain amount of trichlorotoluene at a certain temperature under the protection of nitrogen, reacting for a period of time, and performing vacuum rectification to respectively obtain 3-chloropropionyl chloride and benzoyl chloride. The preparation method has the following beneficial effects: 1) acrylic acid and trichlorotoluene are adopted as raw materials, 3-chloropropionyl chloride is prepared in the presence of a catalyst, and benzoyl chloride with wide application is produced as a byproduct; the reaction route is environment-friendly, the process is simple, no emission is generated, and the requirement of atom economy is met; and the technical problem that toxic raw materials are used in the prior art is solved, and the technical problem that by-products polluting the environment are possibly generated in the prior art is also solved; and 2) the method is low in production cost, and in addition, the reaction route is combined with the specific reaction conditions, so that the yield of the obtained product is quite high and reaches 95% or above.
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Paragraph 0019-0021

(2021/10/27)

Method for producing high-purity 3-chloropropionyl chloride by one-pot method
The invention discloses a method for producing high-purity 3-chloropropionyl chloride through a one-pot method, and belongs to the field of fine chemical engineering. Acrylic acid, hydrochloric acid and thionyl chloride are used as raw materials, in the presence of a phenothiazine catalyst, addition reaction, dehydration and acylating chlorination reaction are performed, and simple distillation is performed to obtain 3-chloropropionyl chloride. In the addition stage, the residual acrylic acid in the reaction liquid is strictly controlled to be less than or equal to 2.0% and the moisture is less than or equal to 1.0%; in the acylating chlorination stage, the content of 3-chloropropionyl chloride is strictly controlled to be greater than or equal to 99.0%, the purity of 3-chloropropionyl chloride obtained by distilling the reaction liquid is greater than or equal to 99.5%, and the yield is 90% or above. The 3-chloropropionyl chloride product obtained by the process can meet the requirements of the market on high-purity 3-chloropropionyl chloride.
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Paragraph 0024-0031

(2021/08/07)

Preparation method of 3-chloropropionyl chloride
The invention relates to a preparation method of 3-chloropropionyl chloride. Beta-propiolactone and bis(trichloromethyl) carbonate react under the action of a catalyst to generate 3-chloropropionyl chloride. The preparation method of 3-chloropropionyl chloride is economical, environmentally friendly, simple in reaction route, little in waste gas, safe and controllable.
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Paragraph 0017-0021

(2021/03/05)

Development of Benzenesulfonamide Derivatives as Potent Glutathione Transferase Omega-1 Inhibitors
Glutathione transferase omega-1 (GSTO1-1) is an enzyme whose function supports the activation of interleukin (IL)-1β and IL-18 that are implicated in a variety of inflammatory disease states for which small-molecule inhibitors are sought. The potent reactivity of the active-site cysteine has resulted in reported inhibitors that act by covalent labeling. In this study, structure-activity relationship (SAR) elaboration of the reported GSTO1-1 inhibitor C1-27 was undertaken. Compounds were evaluated for inhibitory activity toward purified recombinant GSTO1-1 and for indicators of target engagement in cell-based assays. As covalent inhibitors, the kinact/KI values of selected compounds were determined, as well as in vivo pharmacokinetics analysis. Cocrystal structures of key novel compounds in complex with GSTO1-1 were also solved. This study represents the first application of a biochemical assay for GSTO1-1 to determine kinact/KI values for tested inhibitors and the most extensive set of cell-based data for a GSTO1-1 inhibitor SAR series reported to date. Our research culminated in the discovery of 25, which we propose as the preferred biochemical tool to interrogate cellular responses to GSTO1-1 inhibition.
Xie, Yiyue,Tummala, Padmaja,Oakley, Aaron J.,Deora, Girdhar Singh,Nakano, Yuji,Rooke, Melissa,Cuellar, Matthew E.,Strasser, Jessica M.,Dahlin, Jayme L.,Walters, Michael A.,Casarotto, Marco G.,Board, Philip G.,Baell, Jonathan B.
p. 2894 - 2914
(2020/04/08)

Monoterpenoid-based inhibitors of filoviruses targeting the glycoprotein-mediated entry process
In this study, we screened a large library of (+)-camphor and (?)-borneol derivatives to assess their filovirus entry inhibition activities using pseudotype systems. Structure-activity relationship studies revealed several compounds exhibiting submicromolar IC50 values. These compounds were evaluated for their effect against natural Ebola virus (EBOV) and Marburg virus. Compound 3b (As-358) exhibited the good antiviral potency (IC50 = 3.7 μM, SI = 118) against Marburg virus, while the hydrochloride salt of this compound 3b·HCl had a strong inhibitory effect against Ebola virus (IC50 = 9.1 μM, SI = 31) and good in vivo safety (LD50 > 1000 mg/kg). The results of molecular docking and in vitro mutagenesis analyses suggest that the synthesized compounds bind to the active binding site of EBOV glycoprotein similar to the known inhibitor toremifene.
Baev, Dmitriy S.,Maksyutov, Rinat A.,Mordvinova, Ekaterina D.,Pyankov, Oleg V.,Salakhutdinov, Nariman F.,Shcherbakov, Dmitriy N.,Shcherbakova, Nadezhda S.,Sokolova, Anastasiya S.,Tolstikova, Tatyana G.,Yarovaya, Olga I.,Zaykovskaya, Anna V.,Zybkina, Anastasiya V.
(2020/09/09)

Synthesis, molecular docking studies, and absorption, distribution, metabolism, and excretion prediction of novel sulfonamide derivatives as antibacterial agents
A series of novel sulfonamide-amide derivatives were synthesized from 3-(2,4 dichlorophenylamino)-3-oxopropane-1-sulfonylchloride and a variety of amines under solvent-free conditions at room temperature. 3-(2,4-dichlorophenylamino)-3-oxopropane-1 sulfonylchloride was synthesized in four steps starting from 2,4-dichloroaniline and chloropropanoic acid in good yield and purity. The synthesized compounds were screened for their in vitro antibacterial activity against Escherichia coli (ATCC 25922) and Staphylococcus aureus (ATCC 29213). Molecular docking of sulfonamide derivatives into S. aureus tyrosyl-tRNA synthetase (TyrRS)-active site was also performed and among these, 5m and 5g tightly fit the active sites that might be inhibitors of TyrRS for further investigations. Also in the silico metabolism profile, drug-like properties and absorption, distribution, metabolism, excretion and toxicity (ADMET) of the title compounds were calculated by the preADMET server.
Mohebali, Farzaneh,Nazifi, Zahrasadat,Mohamad Reza Nazifi, Seyed,Mohammadian, Hossein,Massah, Ahmad R.
p. 558 - 566
(2019/02/09)

A production device for 5-chloro-indanone and a production method thereof
The present invention relates to a production device for 5-chloro-indanone, including an acrylic acid storage tank, at least two gas liquid reactors connected in series, a thionyl chloride storage tank, at least two first flow reactors connected in series, a 3-chloropropionyl chloride storage tank, a chlorobenzene storage tank, at least two second flow reactors connected in series, and at least two third flow reactors connected in series. A gas outlet of each first flow reactor is connected to a gas inlet of the gas liquid reactor at the rearmost end through a pipeline provided with a condenser. A feeding port of the second flow reactor in the front end is provided with a first aluminium chloride feeding device. A feeding port of the third flow reactor in the front end is provided with a second aluminium chloride feeding device. The invention relates to a method for producing the 5-chloro-indanone by utilizing the production device. The production device and method can achieve continuous cyclic production and a high product yield.
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Paragraph 0021

(2019/04/10)

3 - Chloropropionyl production device
The utility model relates to a 3 - chloropropionyl production device, including acrylic acid storage tank, at least two serially connected gas-liquid reactor, thionyl chloride storage tank, at least two serially connected continuous reactor and 3 - chloropropionyl storage tank; acrylic acid storage tank with the discharge port of the foremost end of the pipeline located in the gas-liquid reactor is connected with feed opening; at the last end of the discharge port of the gas-liquid reactor through the pipeline with the locates at foremost a continuous reactor connected to the feed ports of the, the discharge port of the thionyl chloride storage tank through the pipeline with the locates at foremost a continuous reactor is connected with feed opening; at the last end of the discharge port of the continuous reactor through the pipeline with 3 - chloropropionyl connected to the feed ports of the storage tank; the air outlet of the continuous reactor is provided with a condenser through a pipeline with the last end of the gas-liquid located connected with the inlet of the reactor. The utility model of the 3 - chloropropionyl production equipment to achieve continuous circulation production, high product yield.
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Paragraph 0016; 0017; 0018; 0019

(2019/06/24)

Formamide catalyzed activation of carboxylic acids-versatile and cost-efficient amidation and esterification
A novel, broadly applicable method for amide C-N and ester C-O bond formation is presented based on formylpyrrolidine (FPyr) as a Lewis base catalyst. Herein, trichlorotriazine (TCT), which is the most cost-efficient reagent for OH-group activation, was employed in amounts of ≤40 mol% with respect to the starting material (100 mol%). The new approach is distinguished by excellent cost-efficiency, waste-balance (E-factor down to 3) and scalability (up to >80 g). Moreover, high levels of functional group compatibility, which includes acid-labile acetals and silyl ethers, are demonstrated and even peptide C-N bonds can be formed. In comparison to reported amidation procedures using TCT, yields are considerably improved (for instance from 26 to 91%) and esterification is facilitated for the first time in synthetically useful yields. These significant enhancements are rationalized by activation by means of acid chlorides instead of less electrophilic acid anhydride intermediates.
Huy, Peter H.,Mbouhom, Christelle
p. 7399 - 7406
(2019/08/20)

PROCESS FOR THE MANUFACTURING OF A 3-HALOPROPIONYL HALIDE IN A FLOW REACTOR
The present disclosure relates to a process for the manufacturing of a 3-5 halopropionylhalide, wherein the process comprises the steps of: a) providing a flow reactor comprising a reaction chamber; b) providing reactants comprising: i. acrylic acid; ii. a reaction co-agent selected from the group consisting of N,N-0 disubstituted amides; and iii. a halogenating agent; and c) incorporating the reactants into the reaction chamber of the flow reactor, thereby forming a reaction product stream comprising a 3-halopropionylhalide; wherein the molar ratio of acrylic acid to the halogenating agent is 1 to at least 5 0.8; wherein the temperature of the reaction chamber of the flow reactor is greater than 60°C; and wherein the residence time of the reaction product stream comprising the 3-halopropionylhalide in the reaction chamber of the flow reactor is greater than 10 minutes.
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Page/Page column 25

(2019/07/13)

Discovery of a New Class of Inhibitors of Vaccinia Virus Based on (?)-Borneol from Abies sibirica and (+)-Camphor
A series of the bornyl ester/amide derivatives with N-containing heterocycles were designed and synthesized as vaccinia virus (VV) inhibitors. Bioassay results showed that among the designed compounds, derivatives 6, 13, 14, 34, 36 and 37 showed the best inhibitory activity against VV with the IC50 values of 12.9, 17.9, 3.4, 2.5, 12.5 and 7.5 μm, respectively, and good cytotoxicity. The primary structure–activity relationship (SAR) study suggested that the combination of a saturated N-heterocycle, such as morpholine or 4-methylpiperidine, and a 1,7,7-trimethylbicyclo[2.2.1]heptane scaffold was favorable for antiviral activity.
Sokolova, Anastasiya S.,Yarovaya, Olga I.,Bormotov, Nikolay I.,Shishkina, Larisa N.,Salakhutdinov, Nariman F.
(2018/09/06)

Atom- and Mass-economical Continuous Flow Production of 3-Chloropropionyl Chloride and its Subsequent Amidation
3-Chloropropionyl chloride is a chemically versatile building block with applications in the field of adhesives, pharmaceuticals, herbicides and fungicides. Its current production entails problems concerning safety, prolonged reaction times and the use of excessive amounts of chlorinating reagents. We developed a continuous flow procedure for acid chloride formation from acrylic acid and a consecutive 1,4-addition of hydrogen chloride generating 3-chloropropionyl chloride, as presented in this paper. Up to 94 % conversion was reached in 25 minutes at mild temperatures and pressures. This continuous flow method offers a safer alternative and is highly efficient in terms of consumption of starting product and shorter residence time. Valorization of this building block is exemplified by the synthesis of beclamide, a compound with sedative and anticonvulsant properties. Over 80 % conversion towards this drug was achieved in 1 minute in a continuous flow setup. Further research is needed to telescope the synthesis of 3-chloropropionyl chloride and subsequent beclamide formation without intermediate purification.
Movsisyan, Marine,Heugebaert, Thomas S. A.,Roman, Bart I.,Dams, Rudolf,Van Campenhout, Rudy,Conradi, Matthias,Stevens, Christian V.
supporting information
p. 11779 - 11784
(2018/08/01)

Synthetic method of L-carnosine
The invention discloses a synthetic method of L-carnosine, and belongs to the technical field of organic matter synthesis. The method comprises the following steps: dissolving 3-chloropropionic acid in an organic solvent, and converting the 3-chloropropionic acid by a chloroformylation reagent to form corresponding 3-chloropropionyl chloride; condensing trimethylsilane protected L-histidine and the 3-chloropropionyl chloride to obtain a corresponding amide product; removing protection agents by using water or an alkaline solution to obtain an intermediate; carrying out aminolysis on the intermediate to obtain crude L-carnosine; and purifying the crude L-carnosine to obtain finished L-carnosine. The synthetic method has the advantages of low raw material consumption, short reaction steps, few wastes, high yield, obtaining of high-quality L-carnosine free from hydrazine, and meeting of industrial production demands.
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Paragraph 0005; 0027; 0028; 0029; 0030

(2017/08/28)

Synthesis and in vitro study of novel borneol derivatives as potent inhibitors of the influenza A virus
Herein, we present the design and synthesis of a series of novel heterocyclic derivatives of (-)-borneol and (-)-isoborneol as potent inhibitors of the influenza A virus. All compounds were tested for their toxicity against MDCK cells and for virus-inhibiting activity against the influenza virus A/Puerto Rico/8/34 (H1N1). Compounds 7, 16 and 26 containing a morpholine fragment exhibited the highest efficiency as agents inhibiting the replication of the influenza virus A(H1N1) with selectivity indices of 82, 45 and 65, correspondingly. Derivatives 9 (SI = 23) and 18 (SI = 25) containing a 1-methylpiperazine motif showed moderate antiviral activity. Structure-activity analysis of this new series of borneol derivatives revealed that a 1,7,7-trimethylbicyclo[2.2.1]heptan scaffold is required for the antiviral activity.
Sokolova,Yarovaya,Semenova,Shtro,Orshanskaya,Zarubaev,Salakhutdinov
supporting information
p. 960 - 963
(2017/07/12)

Synthesis and biological activity of heterocyclic borneol derivatives
(figure presented) A series of novel heterocyclic derivatives of (–)-borneol has been prepared by the interaction of (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]-heptan-2-yl 2-chloroacetate and (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 3-chloropropanoate with different N- and S-nucleophiles. The obtained products were screened for antiviral, antiulcer, and analgesic activity.
Sokolova, Anastasiya S.,Yarovaya, Оlga I.,Shtro, Anna A.,Borisova, Marina S.,Morozova, Ekaterina A.,Tolstikova, Tatyana G.,Zarubaev, Vladimir V.,Salakhutdinov, Nariman F.
p. 371 - 377
(2017/09/30)

Identification, Synthesis, and Biological Evaluation of the Major Human Metabolite of NLRP3 Inflammasome Inhibitor MCC950
MCC950 is an orally bioavailable small molecule inhibitor of the NOD-like receptor pyrin domain-containing protein 3 (NLRP3) inflammasome that exhibits remarkable activity in multiple models of inflammatory disease. Incubation of MCC950 with human liver microsomes, and subsequent analysis by HPLC-MS/MS, revealed a major metabolite, where hydroxylation of MCC950 had occurred on the 1,2,3,5,6,7-hexahydro-s-indacene moiety. Three possible regioisomers were synthesized, and coelution using HPLC-MS/MS confirmed the structure of the metabolite. Further synthesis of individual enantiomers and coelution studies using a chiral column in HPLC-MS/MS showed the metabolite was R-(+)- N-((1-hydroxy-1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)-4-(2-hydroxypropan-2-yl)furan-2-sulfonamide (2a). Incubation of MCC950 with a panel of cytochrome P450 enzymes showed P450s 2A6, 2C9, 2C18, 2C19, 2J2, and 3A4 catalyze the formation of the major metabolite 2a, with a lower level of activity shown by P450s 1A2 and 2B6. All of the synthesized compounds were tested for inhibition of NLRP3-induced production of the pro-inflammatory cytokine IL-1β from human monocyte derived macrophages. The identified metabolite 2a was 170-fold less potent than MCC950, while one regioisomer had nanomolar inhibitory activity. These findings also give first insight into the SAR of the hexahydroindacene moiety.
Salla, Manohar,Butler, Mark S.,Pelingon, Ruby,Kaeslin, Geraldine,Croker, Daniel E.,Reid, Janet C.,Baek, Jong Min,Bernhardt, Paul V.,Gillam, Elizabeth M. J.,Cooper, Matthew A.,Robertson, Avril A. B.
p. 1034 - 1038
(2016/12/16)

Safe, selective, and high-yielding synthesis of acryloyl chloride in a continuous-flow system
Acid chlorides are an important class of compounds and their high reactivity and instability has prompted us to develop a straightforward procedure for their synthesis with ondemand and on-site synthesis possibilities. The focus of this report is acryloyl chloride, mainly important for the acrylate and polymer industry. A continuous-flow methodology was developed for the fast and selective synthesis of the otherwise highly unstable acryloyl chloride. Three routes were investigated in a microreactor setup and all three can potentially be used for its production. The methodology was further expanded to the synthesis of other unstable acid chlorides by both the thionyl chloride and the oxalyl chloride mediated processes. The most sustainable method was the oxalyl chloride mediated procedure under solvent-free conditions, in which nearequimolar amounts of carboxylic acid and oxalyl chloride were used in the presence of catalytic amounts of DMF at room temperature. Within 1 to 3 min, nearly full conversions into the acid chlorides were achieved.
Movsisyan, Marine,Heugebaert, Thomas S. A.,Dams, Rudy,Stevens, Christian V.
p. 1945 - 1952
(2018/08/17)

Easily assembled, modular N,O-chelating ligands for Ta(V) complexation: A comparative study of ligand effects in hydroaminoalkylation with N-methylaniline and 4-methoxy-N-methylaniline
The influence of structurally related N,O-chelating ligands with additional heteroatoms (N, O, P, S) on the reactivity of in situ generated tantalum complexes for the hydroaminoalkylation of amines has been explored. Reactivity was probed by evaluating the catalytic ability of these N,O-chelating systems with N-methylaniline and 4-methoxy-N-methylaniline substrates. Enhanced reactivity is observed with amide proligands bearing an ortho-methoxyphenyl group on the nitrogen. 4-Methoxy-N-methylaniline is found to be more prone to undergo C-H functionalization via hydroaminoalkylation than N-methylaniline. The use of the related substrate 2-methoxy-N-methylaniline is not tolerated, and instead C(sp3)-O bond cleavage was observed.
Garcia, Pierre,Payne, Philippa R.,Chong, Eugene,Webster, Ruth L.,Barron, Benedict J.,Behrle, Andrew C.,Schmidt, Joseph A.R.,Schafer, Laurel L.
p. 5737 - 5743
(2013/07/11)

STABILIZED ISOCYANATE GROUP-CONTAINING ETHYLENICALLY UNSATURATED COMPOUND
An object of the present invention is to improve the stability of an ethylenically unsaturated compound having an isocyanate group in the molecule by preventing a polymerization of the ethylenically unsaturated compound. The present invention relates to a stabilizing composition for an isocyanate group-containing ethylenically unsaturated compound, comprising: an isocyanate group-containing ethylenically unsaturated compound (A) which comprises one or more isocyanate groups and one or more ethylenically unsaturated groups in the molecule; and a stabilizing agent (B) which is a compound in which at least one of the ethylenically unsaturated groups in the compound (A) is replaced with an alkyl group which may have a substituent.
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Paragraph 0061; 0062

(2013/12/04)

STABILIZED ISOCYANATE GROUP-CONTAINING ETHYLENICALLY UNSATURATED COMPOUND
An object of the present invention is to improve the stability of an ethylenically unsaturated compound having an isocyanate group in the molecule by preventing a polymerization, a multimerization reaction and a discoloration reaction of the ethylenically unsaturated compound. The present invention relates to a stabilizing composition for an isocyanate group-containing ethylenically unsaturated compound, comprising: an isocyanate group-containing ethylenically unsaturated compound (A) which comprises one or more isocyanate groups and one or more ethylenically unsaturated groups in the molecule; and a stabilizing agent (B) which is a compound in which at least one of the ethylenically unsaturated groups in the compound (A) is replaced with an alkyl halide group or an amino alkyl group which may have a substituent.
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Paragraph 0091

(2013/12/04)

Design and synthesis of 3-(azol-1-yl)phenylpropanes as microbicidal spermicides for prophylactic contraception
We designed a series of 25 3-(azol-1-yl)phenylpropanes which yielded 10 compounds (3, 4, 7, 8, 13, 14, 19, 21, 23, 26) that irreversibly immobilized 100% human sperm at 1% (w/v) concentration in 60 s; 12 compounds (8, 9, 15, 16, 19-21, 23-25, 27, 28) that showed potent microbicidal activity at 12.5-50 μg/mL against Trichomonas vaginalis; and 17 compounds (3-11, 13, 15, 19, 21, 23, 26, 28, 30) that exhibited potent anticandida activity with minimum inhibitory concentration (MIC) of 12.5-50 μg/mL. Almost all the compounds exhibited high level of safety towards normal vaginal flora (Lactobacillus) and human cervical (HeLa) cells in comparison to the marketed spermicide nonoxynol-9 (N-9). All the biological activities were evaluated in vitro. Two compounds (4, 8) with good safety profile exhibited multiple (spermicidal, antitrichomonas and anticandida) activities, warranting further lead optimization for furnishing a prophylactic vaginal contraceptive.
Kumar, Lalit,Sarswat, Amit,Lal, Nand,Jain, Ashish,Kumar, Sumit,Kiran Kumar,Maikhuri, Jagdamba P.,Pandey, Atindra K.,Shukla, Praveen K.,Gupta, Gopal,Sharma, Vishnu L.
supporting information; experimental part
p. 176 - 181
(2011/02/27)

Dithiocarbamic acid esters as anticancer agent. Part 1: 4-Substituted-piperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl esters
A variety of 4-N atom substituted derivatives were synthesized and evaluated for their in vitro anticancer activities using 4-methylpiperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl ester 4 as lead compound. Among them, compound 6a without any substituent on 4-N atom (R1 = H) was found to be the most active anticancer agent with IC50 = 5.3 μM against HL-60 and IC50 = 11.5 μM against Bel-7402, respectively. Increase in the polarity and/or introduction of suitable acyl groups at the 4-N atom of the lead compound 4 are favorable for the improvement of activity.
Hou, Xueling,Ge, Zemei,Wang, Tingmin,Guo, Wei,Cui, Jingrong,Cheng, Tieming,Lai, Chingshan,Li, Runtao
p. 4214 - 4219
(2007/10/03)

Synthesis and evaluation of 7-hydroxyindan-1-one-derived chiral auxiliaries
A series of novel chiral acetals were prepared from 7-hydroxyindan-1-one and a variety of substituted chiral nonracemic C2-symmetric 1,2-ethanediols (R = Me, Ph, CH2OMe, CH2OBn, CH 2O(1-Np), and i-Pr). These acetals were evaluated as chiral auxiliaries for use in asymmetric synthesis. A high degree of stereochemical induction was observed in the diethylaluminum chloride-promoted Diels-Alder reaction of an acrylate derivative (R = i-Pr) with cyclopentadiene (91:9 dr). This demonstrated that these acetals could serve as effective chiral directors in asymmetric substrate-directed reactions.
Narine, Arun A.,Wilson, Peter D.
p. 413 - 419
(2007/10/03)

METHOD FOR PRODUCING (METH)ACRYLATE DERIVATIVE HAVING ISOCYANATE GROUP
The invention aims to provide a method whereby (meth)acrylate derivatives having an isocyanate group can be obtained in high yield by dehydrochlorination of 3-chloropropionate derivatives having an isocyanate group under industrially advantageous and mild conditions, and the content of residual hydrolyzable chlorine can be reduced. A method for producing a (meth)acrylate derivative having an isocyanate group comprises performing dehydrochlorination of a 3-chloropropionate derivative having an isocyanate group in the presence of a basic nitrogen compound having a tertiary nitrogen, the tertiary nitrogen of the basic nitrogen compound having
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Page/Page column 18-19

(2008/06/13)

On the reactions between phosphorus pentachloride and lactones
Reactions between PCl5 and substituted or unsubstituted β-, γ- and ε-lactones have been investigated. Although γ-butyrolactone substituted at α-position with an alkyl radical has given phosphorylated products of both cyclic ethers and chlorinated carboxylic acid chlorides along with γ-chlorobutanoic acid chloride, halogen substituted γ-butyrolactone such as α-bromo-γ-butyrolactone yielded α-bromo-γ-chlorobutanoic acid chloride in similar manner with β-propiolactone which gives β-chloropropionic acid chloride. The nature of radicals present at γ-position also affects the reaction products. Methyl or heptyl radicals yielded different products; in the latter case phosphorylated products were not isolated. The reaction pathway of ε-caprolactone with PCl5 is changed by the temperature of the reaction mixture. It reacts at 20-30°C to give α,α-dichlorooxepane and ε-chlorohexanoic acid chloride, while a phosphorylated product was observed at 60-70°C. Possible mechanisms of these reactions are discussed.
Ismaili, Valeh Mehralioglu,Aydin, Adnan,Kantaeva
p. 137 - 142
(2007/10/03)

Effect of Spectral Shifts on the Resolution of trans-1-(2-Naphthyl)-2-phenylethene Conformer UV Spectra Based on Principal Component Analysis with Self-Modeling
Application of principal component analysis with self-modeling (PCA-SM) to a matrix consisting of UV absorption spectra of trans-1-(2-naphthyl)-2-phenylethene (NPE) at different temperatures leads to two resolved pure component spectra.The significance of this resolution is evaluated by examining the spectra of three conformationally restricted NPE analogues: trans-1--2-phenylethene (1-MPE), trans-1--2-phenylethene (3-MPE), and trans-3-styrylidenebenzindane (BPE).It is established that temperature effects on the UV spectra of NPE reflect primarily the temperature dependence of the individual conformer spectra rather than any changes in conformer composition.Pure component UV absorption spectra generated by PCA-SM on the spectrothermal matrix of NPE UV spectra bear no resemblance to either the analogue spectra or the known NPE conformer spectra.PCA-SM treatment of a simulated spectral matrix shows that spectral shifts are reflected predictably in the appearance of the second eigenvector.The implications of our findings on results obtained from other PCA-SM spectral resolutions of spectrothermal matrices are discussed.
Saltiel, Jack,Choi, Jong-Oh,Sears, Donald F. Jr.,Eaker, David W.,Mallory, Frank B.,Mallory, Clelia W.
p. 13162 - 13170
(2007/10/02)

α-FLUOROACRYLIC ACID CHLORANHYDRIDE
Kinetic studies were carried out on the reaction of 2-fluoro-3-chloropropanoic acid and other halo- and methoxy-substituted propanoic acids with thionyl chloride at 50-110 deg C.The catalytic dehydro-chlorination of 2-fluoro-3-chloropropanoic acid chloranhydride by tertiary amines and their salts was investigated.Dimethylaniline chlorohydrate was shown to be an effective catalyst, providing maximum dehydrochlorination at a concentration of 20percent.A mechanism for the reaction was proposed.
Boguslavskaya, L. S.,Morozova, T. V.
p. 716 - 720
(2007/10/02)

Serotonin Receptor Affinity of Cathinone and Related Analogues
A series of cathinone (α-aminopropiophenone) analogues was examined using the isolated rat fundus preparation. (S)-(-)-Cathinone possesses twice the serotonin receptor affinity of (+/-)-cathinone and four times the affinity of racemic amphetamine.Several derivatives of cathinone were found to either possess a lower affinity than the parent compound or did not interact with the receptors in a competitive manner.Several novel analogues, 1-(aminomethyl)-3,4-dihydronaphthalene hydrochloride (3), 4-(aminomethyl)-3-chromene hydrochloride (4b), as well as its 6-methoxy derivative, 4a, interact with serotonin receptors but in a fashion which is, most likely, dissimilar to the interaction of the substituted cathinone analogues.
Glennon, Richard A.,Liebowitz, Stephen M.
p. 393 - 397
(2007/10/02)

Process for preparing amides by reaction in presence of molecular sieve
There is provided a process for preparing amides which comprises reacting an amine, or an amide, and an acid halide, or anhydride, in suitable molecular proportions, in an inert organic diluent, in the presence of an effective amount of a molecular sieve, until the reaction is completed, separating the molecular sieve, and recovering the amide from the organic mother liquor.
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(2008/06/13)

Process for the simultaneous preparation of 2,5-dioxo-1,2-oxa-phospholanes and β-halogenpropionic acid halide
2,5-Dioxo-1,2-oxa-phospholanes of the formula (I) STR1 wherein R1 is an organic radical and R2 and R3 each also represents an organic radical or hydrogen, are prepared by reacting 2-haloformylethyl-phosphinic acid halides of the formula (II) STR2 wherein R1, R2 and R3 are defined as in formula (I) and X means Cl or Br, preferably Cl, with an approximatey equimolar quantity of acrylic acid. The compounds (II) may also be produced in the reaction batch and in situ by reacting about equimolar quantities of a dihalophosphine of the formula (III) STR3 with an α,β-unsaturated acid (IV) In the formulae (III) and (IV) R1, R2, R3 and X are defined as indicated above. In the reaction there is formed, in addition to the compounds (I), practically exclusively β-halopropionic acid and no free hydrogen halide. The phospholanes (I) are valuable flame retarding agents for plastics, intermediates, for example, for the synthesis of biocidals etc.
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(2008/06/13)

3-[3',4'-Dichloro-6'-alkyl-phenyl]-Δ2 -pyrazoline derivatives and their use as optical brighteners
Novel pyrazolines are obtained by condensation of substituted propiophenones or vinyl-phenyl-ketones with substituted phenyl hydrazines. The products are useful as optical brighteners of a great variety of the shade of their fluorescence and of an improved fastness to light.
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(2008/06/13)