cas 836-42-0, 4-(Benzyloxy)benzyl chloride

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Topochemical polymerisation of assembled diacetylene macrocycle bearing dibenzylphosphine oxide in solid state
Novel diacetylene macrocycles 1 and 2 bearing dibenzylphosphine oxide were synthesised via Eglinton acetylenic intramolecular coupling. The X-ray analysis of crystals of macrocycles 1 and 2 demonstrated that the better-aligned tubular supramolecular structure was formed in macrocycle 1 than in macrocycle 2, which provided the possibility of diacetylene topochemical polymerisation in solid state of macrocycle 1. UV–vis, Raman spectroscopy and X-ray analysis indicated that the crystals of macrocycle 1 could undergo topochemical diacetylene polymerisation only on their surface by light irradiation; differential scanning calorimetry, solid-state 13C NMR spectroscopy and solubility test demonstrated that the crystals of macrocycle 1 could undergo diacetylene topochemical polymerisation inside solid by heat. As expected, based on the topological analysis of crystal structure, the crystals of macrocycle 2 could not undergo diacetylene topochemical polymerisation either by light irradiation or heat.
Zhang, Xiaoning,Deng, Chao,Wang, Meng,Liu, Xin,Lin, Chen,Peng, Luming,Wang, Leyong
p. 94 - 101
(2017)
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PO functional group-containing cryptands: From supramolecular complexes to poly[2]pseudorotaxanes
Two types of cryptand-based host-guest complexes were constructed successfully, in which PO functional groups were located at the different positions of the third arms. Consequently, supramolecular poly[2]pseudorotaxanes with almost linear and zigzag shapes were formed in the solid state. This journal is
Wang, Qi,Cheng, Ming,Xiong, Shuhan,Hu, Xiao-Yu,Jiang, Juli,Wang, Leyong,Pan, Yi
p. 2667 - 2670
(2015)
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Fumarate related impurity and preparation method and application thereof (by machine translation)
The preparation method of the related impurities comprises the following steps: No.No.No. STR8No.No. wherein the (I) preparation method, of ,R the related impurities is. shown, in the specification, and the preparation method of, the 1 present, application, further, discloses, the preparation method, and of the related impurities. (by machine translation)
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(2020/02/04)

Nickel-Catalyzed Asymmetric Reductive Arylbenzylation of Unactivated Alkenes
Herein, we report a nickel-catalyzed asymmetric two-component reductive dicarbofunctionalization of aryl iodide-tethered unactivated alkenes using benzyl chlorides as the challenging coupling partner. This arylbenzylation reaction enables the efficient synthesis of diverse benzene-fused cyclic compounds bearing a quaternary stereocenter with a high tolerance of sensitive functionalities in highly enantioselective manner. The preliminary mechanistic investigations suggest a radical chain reaction mechanism.
Jin, Youxiang,Yang, Haobo,Wang, Chuan
supporting information
p. 2724 - 2729
(2020/04/02)

Benzofuran compound and its preparation, use (by machine translation)
The invention relates to a benzofuran compound and its preparation, use, its structural formula such as formula (I) as shown: Wherein R1 , R2 , R4 Are selected from hydrogen, C1 - C5 Alkyl, nitro, halogen, ester, hydroxy, amino, amide base or alkoxyl; R3 Hydrogen, C1 - C5 Alkyl, benzyl, aromatic or heteroaromatic group. The invention also relates to the benzofuran compounds in inhibiting the application of gram-positive to be used repeatedly. The invention relates to 3 - oxime substituted benzene and furan structure aromatic ring as the center, the establishment and optimize the preparation method of the compound, and on the preparation of novel compound of the bacteriostatic screening experiment, through initial bacteriostatic test to confirm that preparation compound has broad-spectrum bacteriostatic activity. (by machine translation)
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Paragraph 0063-0064

(2017/08/18)

Beyond the affinity for protein kinase C: Exploring 2-phenyl-3-hydroxypropyl pivalate analogues as C1 domain-targeting ligands
Over the past fifteen years, we reported the design and synthesis of different series of compounds targeting the C1 domain of protein kinase C (PKC) that were based on various templates. Out of the pivalate templates, 2-[4-(benzyloxy)phenyl]-3-hydroxypropyl pivalate (compound 1) emerged as the most potent and promising PKCα ligand, showing a Ki value of 0.7 μM. In the present contribution our efforts are aimed at better understanding which structural modifications of the pivalate template are allowed for its affinity to the C1 domain of PKC to be preserved or increased. To this aim, thirteen novel analogues of 1 were designed and their interaction with the target was evaluated in silico. Designed compounds were then prepared and fully characterized as well as their affinity for the α and δ isoforms of PKC evaluated. Additionally, in order to investigate the role of chirality in the ligand-target interaction, the pure enantiomers of the most interesting PKC ligands were prepared and their affinity for PKC isoforms was determined. Results from our study revealed that: i) the presence of the ester function seems to be essential for the ligand-target interaction; ii) only a few structural modifications at the ester group are allowed for the C1 domain affinity to be preserved; and iii) the [3H]PDBu replacement experiments showed that the C1 domain of PKC does not exhibit enantiopreference for the pure stereoisomers of tested compounds. Altogether our observations provide further insights into the ligand-target interactions of the PKC C1 domain and represent a step-forward in future development of more specific and effective PKC ligands. This journal is
Rossi, Daniela,Talman, Virpi,Genn?s, Gustav Boije Af,Marra, Annamaria,Picconi, Pietro,Nasti, Rita,Serra, Massimo,Ann, Jihyae,Amadio, Marialaura,Pascale, Alessia,Tuominen, Raimo K.,Yli-Kauhaluoma, Jari,Lee, Jeewoo,Collina, Simona
p. 547 - 554
(2015/04/27)

Strategies for large-scale synthesis of coelenterazine for in vivo applications
A new application of two Negishi-type coupling reactions for the synthesis of coelenterazine is reported. The synthesis of coelenterazine in high purity on a gram scale will enable numerous approaches to bioluminescence imaging and possibly photodynamic therapy of deep-seated tumors. Coelenterazine is the substrate for several luciferases, among them Gaussia luciferase (gLuc). This synthesis starts with pyrazin-2-amine and uses inexpensive starting materials and catalysts. Georg Thieme Verlag Stuttgart New York.
Shrestha, Tej B.,Troyer, Deryl L.,Bossmann, Stefan H.
p. 646 - 652
(2014/03/21)

Structural insights into the substrate specificity of bacterial copper amine oxidase obtained by using irreversible inhibitors
Copper amine oxidases (CAOs) catalyse the oxidation of various aliphatic amines to the corresponding aldehydes, ammonia and hydrogen peroxide. Although CAOs from various organisms share a highly conserved active-site structure including a protein-derived cofactor, topa quinone (TPQ), their substrate specificities differ considerably. To obtain structural insights into the substrate specificity of a CAO from Arthrobacter globiformis (AGAO), we have determined the X-ray crystal structures of AGAO complexed with irreversible inhibitors that form covalent adducts with TPQ. Three hydrazine derivatives, benzylhydrazine (BHZ), 4-hydroxybenzylhydrazine (4-OH-BHZ) and phenylhydrazine (PHZ) formed predominantly a hydrazone adduct, which is structurally analogous to the substrate Schiff base of TPQ formed during the catalytic reaction. With BHZ and 4-OH-BHZ, but not with PHZ, the inhibitor aromatic ring is bound to a hydrophobic cavity near the active site in a well-defined conformation. Furthermore, the hydrogen atom on the hydrazone nitrogen is located closer to the catalytic base in the BHZ and 4-OH-BHZ adducts than in the PHZ adduct. These results correlate well with the reactivity of 2-phenylethylamine and tyramine as preferred substrates for AGAO and also explain why benzylamine is a poor substrate with markedly decreased rate constants for the steps of proton abstraction and the following hydrolysis. The Authors 2011. Published by Oxford University Press on behalf of the Japanese Biochemical Society. The Authors 2011. Published by Oxford University Press on behalf of the Japanese Biochemical Society. All rights reserved.
Murakawa, Takeshi,Hayashi, Hideyuki,Taki, Masayasu,Yamamoto, Yukio,Kawano, Yoshiaki,Tanizawa, Katsuyuki,Okajima, Toshihide
experimental part
p. 167 - 178
(2012/07/13)

An acid-promoted novel skeletal rearrangement initiated by intramolecular ipso-Friedel-Crafts-type addition to 3-alkylidene indolenium cations
An acid-promoted novel skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to 3-alkylidene indolenium cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and intramolecular Pictet-Spengler reaction proceeded sequentially, producing tricyclic indole derivatives.
Yokosaka, Takuya,Nemoto, Tetsuhiro,Hamada, Yasumasa
scheme or table
p. 5431 - 5433
(2012/07/03)

Discovery of highly potent and selective benzyloxybenzyl-based peroxisome proliferator-activator receptor (PPAR) δ agonists
A series of 1,4-benzyloxybenzylsulfanylaryl carboxylic acids were prepared and their activities for PPAR receptor subtypes (α, δ, and γ) with potential indications for the treatment of dyslipidemia were investigated. Analog 13a displayed the greatest binding affinity (IC50 = 10 nM) and selectivity (120-fold) for PPARδ over PPARα. Many of the analogs investigated were found to be highly selective for PPARδ and were dependent on the point of attachment of the substituent. In the 1,4-series, analog 28e was found to be the most potent (IC50 = 1.7 nM) and selective (>1000-fold) compound for PPARδ. None of the compounds tested showed appreciable binding affinity for PPARγ.
Bratton, Larry D.,Filzen, Gary F.,Geyer, Andrew,Hoffman, Jennifer K.,Lu, Gina,Pulaski, Jim,Trivedi, Bharat K.,Unangst, Paul C.,Xu, Xiangyang
p. 3624 - 3629
(2008/02/13)

Synthesis and preliminary evaluation of anticonvulsant activity of some [4-(benzyloxy)benzoyl]-and [4-(benzyloxy)benzyl]aminoalkanol derivatives
A variety of appropriate [4-(benzyloxy)benzoyl]- and [4-(benzyloxy)benzyl] aminoalkanol derivatives [I-XVII] was synthesized and evaluated for anticonvulsant activity using the maximal electroshock (MES) and subcutaneous pentylenetetrazole (ScMet) tests in mice and rats. Neurotoxicity (TOX) was determined by the rotorod test. The most active compounds in the MES test in mice were the appropriate 4-(benzyloxy) benzyl derivatives of (R,S)- and S-(+)-2-amino-1-butanol [XI, XIII], 3-[4-(benzyloxy)benzyl]amino-3-methyl-1- butanol [XV], and S-(+)-2-[4-(benzyloxy)benzyl]amino-3-methyl-1-butanol [XVI] - all exhibiting 100% anti-MES protection (at 30 mg/kg, mice, i.p.) and non-toxic in the active doses. 4-[4-(Benzyloxy)benzyl]amino-1-butanol [X] exhibited activity in both MES and ScMet (100 mg/kg, mice, i.p., 100% anticonvulsant protection, 0.5 h and 4 h after administration, respectively).
Waszkielewicz, Anna M.,Cegla, Marek,Marona, Henryk
p. 147 - 157
(2008/09/17)

Selective cleavage of allyl and propargyl ethers to alcohols catalyzed by Ti(O-i-Pr)4/MXn/Mg
(Chemical Equation Presented) Allyl and propargyl ethers were effectively deallylated or depropargylated to the parent alcohols via a C-O bond cleavage catalyzed by a low-valent titanium reagent (LVT), Ti(O-i-Pr)4/TMSCI/ Mg or Ti(O-i-Pr)4/MgBr2/Mg, under mild reaction conditions. Differentiation between the allyl and propargyl ethers was achieved by the reaction in the presence of AcOEt as an additive. The reagent also catalyzed intra- and intermolecular cyclotrimerization reactions of alkynes to substituted benzenes.
Ohkubo, Mutsumi,Mochizuki, Sayaka,Sano, Takeshi,Kawaguchi, Yuuki,Okamoto, Sentaro
p. 773 - 776
(2007/10/03)

2-Benzyl and 2-phenyl-3-hydroxypropyl pivalates as protein kinase C ligands
A series of 2-benzyl and 2-phenyl-3-hydroxypropyl pivalates designed to incorporate the principal pharmacophores of phorbol esters have been synthesized and tested as PKC-α ligands. Among the analogues, 13c exhibited the most potent binding affinity with a Ki = 0.7 μM. The synthesized analogues were subjected to molecular modeling analysis based on two alternative models of the phorbol pharmacophore and a docking study of 13c was carried out.
Lee, Jeewoo,Lee, Ju-Hyun,Kim, Su Yeon,Perry, Nicholas A.,Lewin, Nancy E.,Ayres, Jolene A.,Blumberg, Peter M.
p. 2022 - 2031
(2007/10/03)

Total synthesis of (-)-ephedradine A: An efficient construction of optically active dihydrobenzofuran-ring via C-H insertion reaction
The stereocontrolled total synthesis of (-)-ephedradine A (1) has been accomplished. Construction of optically active dihydrobenzofuran-ring was performed by a novel asymmetric C-H insertion reaction. After an intramolecular ester-amide exchange reaction and a Sharpless asymmetric aminohydroxylation reaction, construction of the complex macrocyclic ring was performed by Ns-strategy and an intramolecular aza-Wittig reaction. Graphical Abstract.
Kurosawa, Wataru,Kobayashi, Hideki,Kan, Toshiyuki,Fukuyama, Tohru
p. 9615 - 9628
(2007/10/03)

Compound
There is provided a compound of Formula I 1 wherein each T is independently selected from H, hydrocarbyl, —F—R, and a bond with one of D, E, P or Q, or together with one of P and Q forms a ring; Z is a suitable atom the valency of which is m; D, E and F are each independently of each other an optional linker group, wherein when Z is nitrogen E is other than CH2 and C═O; P, Q and R are independently of each other a ring system; and at least Q comprises a sulphamate group.
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Page/Page column 81

(2008/06/13)

Stereocontrolled total synthesis of (-)-ephedradine a (orantine)
The stereocontrolled total synthesis of (-)-ephedradine A has been accomplished. The synthesis features an asymmetric C-H insertion reaction, an intramolecular ester-amide exchange reaction, and a Sharpless asymmetric aminohydroxylation reaction. Construction of the complex macrocyclic ring was performed by Ns-strategy and an intramolecular aza-Wittig reaction. Copyright
Kurosawa, Wataru,Kan, Toshiyuki,Fukuyama, Tohru
p. 8112 - 8113
(2007/10/03)

Thiol compounds, their production and use
Compounds represented by general formula (1) or salts thereof which have a matrix metalloprotease inhibitory activity and are useful as drugs, wherein the rings A and B represent each an optionally substituted homocycle or heterocycle, etc.; R1s are the same or different and each represents hydrogen, optionally substituted hydrocarbyl, acyl, etc.; X1represents a bond, optionally substituted divalent aliphatic hydrocarbyl, etc.; X2represents a bond, optionally substituted divalent aliphatic hydrocarbyl, —O—, etc.; Ys are the same or different represents hydrogen, optionally substituted hydrocarbyl, oxo, etc.; m is 0 or 1; n is an integer of 1 to 3; q1is an integer of 1 to 2n+4; and q2is an integer of 0 to 2n+3, provided that q1+q2is 2n+4.
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(2008/06/13)

Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents
Structure-activity relationship studies of a new series of tripentones (thieno[2,3-b]pyrrolizin-8-ones), led us to prepare several derivatives with antiproliferative activities. The most promising 3-(3-hydroxy-4-methoxyphenyl)thieno[2,3-b]pyrrolizin-8-one 20 (leukemia L1210, IC50 = 15 nM) was shown to be a potent inhibitor of tubulin polymerization.
Lisowski, Vincent,Enguehard, Cecile,Lancelot, Jean-Charles,Caignard, Daniel-Henri,Lambel, Stephanie,Leonce, Stephane,Pierre, Alain,Atassi, Ghanem,Renard, Pierre,Rault, Sylvain
p. 2205 - 2208
(2007/10/03)

Purine derivatives and medicinal use thereof
A novel purine derivative exhibiting an effect to control inflammatory symptoms characteristic to nephritis and a medicine comprising this compound as an effective ingredient are provided. The compound is represented by the following general formula (I), wherein R1 is a hydrocarbon group having 17 or less carbon atoms and R2 is a hydrocarbon group having 16 or less carbon atoms, wherein one or more CH2 g roups in the hydrocarbon group which 7013 do not directly bind with the carbon atom at 2 or 7 position of the purine ring replaced are by carbonyl groups, sulfonyl groups, O, or S and/or one or more CH groups in the hydrocarbon group which do not directly bind with the carbon atom at 2 or 7 position of the purine ring are replaced by N, C-halogen, or C—C≡N, or a pharmaceutically acceptable salt thereof.
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(2008/06/13)

COMPOUNDS
This invention relates to novel carboxylic acid indole compounds and compositions for use in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).
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(2008/06/13)

6-(Alkylamino)-9-benzyl-9H-purines. A New Class of Anticonvulsant Agents
Several 9-alkyl-6-substituted-purines were synthesized and tested for anticonvulsant activity against maximal electroshock-induced seizures (MES) in rats.Most compounds were prepared in three steps from 5-amino-4,6-dichloropyrimidine or in two steps via alkylation of 6-chloropurine.Potent anticonvulsant activity against MES resided in compounds that contain a benzyl substituent at the 9-position of 6-(methylamino)- or 6-(dimethylamino)purine.Among commonly used agents for control of seizures, this type of structure represents a new class of potent anticonvulsant agents.
Kelley, James L.,Krochmal, Mark P.,Linn, James A.,McLean, Ed W.,Soroko, Francis E.
p. 606 - 612
(2007/10/02)

Biomimetic hydroxylation using oxo-iron systems: Correlation between the nature of the active species and distribution of the oxidized products
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Ono,Katsube
p. 1267 - 1276
(2007/10/02)

Method for preparing 4-hydroxyphenylacetic acid
A novel process for preparing 4-hydroxyphenylacetic acid which is useful as an intermediate for pharmaceutical is provided. A method for preparing 4-hydroxyphenylacetic acid comprising the steps of first reacting benzyl phenyl ether with formaldehyde and hydrogen chloride to form 4-benzyloxybenzyl chloride, second reacting the resultant 4-benzyloxybenzyl chloride with an alkali metal cyanide in at least one solvent selected from the group consisting of water and an organic solvent to form 4-benzyloxyphenylacetonitrile, and hydrolyzing the resultant 4-benzyloxyphenylacetonitrile in the presence of an acid catalyst.
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(2008/06/13)

Studies on the Chemical Constituents of Rutaceous Plants. Part 45. Novel Phenyl Propanoids: Cuspidiol, Boninenal, and Methyl Boninenalate
Cuspidiol, boninenal, and methyl boninenalate were established as having the structures 3-phenyl>propanol (1), (E)-3-phenyl>propenal (2), and (E)-3-phenyl>propenal (3) respectively.The three compounds were also independently synthesized.
Ishii, Hisashi,Ishikawa, Tsutomu,Tohojoh, Toshiaki,Murakami, Keiko,Kawanable, Eri,et al.
p. 2051 - 2058
(2007/10/02)

Methanolysis (Solvolysis) and Synthesis of 4'-Substituted 4-Benzyloxybenzyl Chlorides and Some Related Compounds: Comparisons with the Corresponding Benzoyl Compounds
The kinetics of methanolysis (solvolysis) in 97.4percent MeOH-dioxan of a series of 4'-substituted 4-benzyloxybenzyl chlorides, and of 4-anisyl, 4-phenoxybenzyl, and benzyl chlorides have been studied and discussed, including comparisons with the data for the corresponding series of benzoyl chlorides, previously reported by us.The 4'-substituted precursor alcohols, chlorides, and product methyl ethers are all new compounds. 4-Anisyl chloride and the series of benzyloxybenzyl chlorides react by the SN1 mechanism, whereas benzyl chloride react by the SN2 mechanism. 4-Phenoxybenzyl chloride shows intermediate behaviour.A similar pattern was observed with the corresponding benzoyl compounds.In both series the reactivity order is CH3O > 4'-CH3C6H4CH2O (-0.76) >C6H5CH2O (-0.74) > 4'-ClC6H4CH2O (-0.69) > 4'-NO2C6H4CH2O (-0.60) > C6H5O > H (values in paranthesis are new ?+ values).At 25 deg C the overall range of rates is 4290 in the benzyl series, compared with only 2.42 in the benzyl series.The Arrhenius parameters in the two series demonstrate, however, an underlying similarity with obvious differences superimposed.In both series, the introduction of 4-OR groups leads to a ΔS increase of ca. 40 J mol-1 K-1.In the benzyl series this is accompanied by ΔE decreases of ca. 6-10 kJ mol-1 whereas in the benzoyl series ΔE values increase by ca. 10-15 kJ mol-1.The equation log k = log k0 + n in mixtures with increasing content of dioxan, was used to study the rate dependence on MeOH concentration.Values of n are ca. 5 between 97.4 and 8.3percent MeOH, and ca. 3 between 83.3 and 50.0percent MeOH.
Jorge, Jorge Armando Luis,Kiyan, Nilo Zengo,Miyata, Yukino,Miller, Joseph
p. 100 - 103
(2007/10/02)

Studies of enzyme-mediated reactions. Part 12. Stereochemical course of the decarboxylation of (2S)-tyrosine to tyramine by microbial, mammalian, and plant systems.
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Battersby,Chrystal,Staunton
p. 31 - 42
(2007/10/02)