cas 129368-70-3, (6-BROMOHEXYLOXY)-TERT-BUTYLDIMETHYL-

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Effective synthesis of ferrulactone II based on the use of 2-carboxyethyltriphenylphosphonium bromide
A simple synthesis of S,3Z-dodecen-11-olide, a component of the aggregation pheromone of the rusty grain beetle Cryptolestes ferrugineus (Stephen), was developed.The key stage was Wittig olefination of C9-aldehyde, prepared from S-propylene oxide, with C3
Cheskis, B. A.,Shpiro, N. A.,Moiseenkov, A. M.
p. 760 - 763
(1993)
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A novel method for direct conversion of tetrahydropyranyl ethers into t-butyldimethylsilyl ethers with t-butyldimethylsilyl triflate and dimethyl sulfide
Direct conversion of THP ethers into TBS ethers has been achieved with TBSOTf and dimethyl sulfide in dichloromethane.
Kim,Kee
p. 2899 - 2900
(1990)
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Synthesis and antitumor activity of novel pyridinium fullerene derivatives
Purpose: We have previously reported that some cationic fullerene derivatives exhibited anticancer activity, and they are expected to be a potential lead compound for an anti-drug resistant cancer agent. However, they are bis-adducts and a mixture of multiple regioisomers, which cannot be readily separated due to the variability of substituent positions on the fullerene cage. To overcome this issue, we evaluated the antiproliferative activities of a set of mono-adduct derivatives and examined their structure-activity relationship. In addition, the in vivo antitumor activity of selected derivatives was also examined. Methods: Nineteen pyridinium fullerene derivatives were newly designed and synthesized in this study. Their antiproliferative activities were evaluated using several cancer cell lines including drug-resistant cells. Furthermore, in vivo antitumor activity of several derivatives was investigated in mouse xenograft model of human lung cancer. Results: The derivatives inhibited the proliferation of cancer cell lines, including cisplatin-resistant cells and doxorubicin-resistant cells. It was also shown that compound 10 (10 μM), 13 (10 μM) and cis-14 (10 μM) induced the intracellular oxidative stress. In addition, compound 13 (20 mg/kg) and cis-14 (15 mg/kg) significantly exhibited antitumor activity in mouse xenograft model of human lung cancer. Conclusion: We synthesized a novel set of mono-adduct fullerene derivatives functionalized with pyridinium groups and found that most of them show potent antiproliferative activities against cancer cell lines and some of them show significant antitumor activities in vivo. We propose that these fullerene derivatives serve as the lead compounds for a novel type of antitumor agents.
Yasuno, Takumi,Ohe, Tomoyuki,Ikeda, Hitomi,Takahashi, Kyoko,Nakamura, Shigeo,Mashino, Tadahiko
p. 6325 - 6337
(2019)
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Studies directed towards the total synthesis of (±)-himbacine
The synthesis of aldehyde 11a is reported based upon the intramolecular Diels-Alder reaction of triene 10, the butenolide-diene part of which was obtained in one step via the condensation of the enolate derived from the (Z)-enoate ester 5 with 2-acetoxypropanal. Aldehyde 11a possesses the correct stereochemistry of the tricyclic part of himbacine, an important muscarine receptor antagonist.
De Baecke, Govert,De Clercq, Pierre J.
p. 7515 - 7518
(1995)
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Weinreb Amide, Ketone and Amine as Potential and Competitive Secondary Molecular Stations for Dibenzo-[24]Crown-8 in [2]Rotaxane Molecular Shuttles
This paper reports the synthesis and study of new pH-sensitive DB24C8-based [2]rotaxane molecular shuttles that contain within their axle four potential sites of interaction for the DB24C8: ammonium, amine, Weinreb amide, and ketone. In the protonated state, the DB24C8 lay around the best ammonium site. After either deprotonation or deprotonation-then-carbamoylation of the ammonium, different localizations of the DB24C8 were seen, depending on both the number and nature of the secondary stations and steric restriction. Unexpectedly, the results indicated that the Weinreb amide was not a proper secondary molecular station for the DB24C8. Nevertheless, through its methoxy side chain, it slowed down the shuttling of the macrocycle along the threaded axle, thereby partitioning the [2]rotaxane into two translational isomers on the NMR timescale. The ketone was successfully used as a secondary molecular station, and its weak affinity for the DB24C8 was similar to that of a secondary amine.
Coutrot, Frédéric,Gauthier, Maxime
supporting information
p. 17576 - 17580
(2021/12/09)

Preparation method of alkyl nitrile compound
The invention discloses a preparation method of an alkyl nitrile compound shown as formula I. The preparation method comprises the following step: in a solvent, in the presence of an additive, carrying out substitution reaction as shown in the specification on a cyanation reagent and an alkyl halide shown as formula II to obtain the alkyl nitrile compound shown as formula I, wherein the cyanationreagent is Zn (CN) 2 and/or Cu (CN) 2; the additive is one or more of an inorganic base, an organic base and a quaternary ammonium salt.
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Paragraph 0101-0103

(2020/05/14)

LIPID NANOPARTICLE
PROBLEM TO BE SOLVED: To provide lipid nanoparticles useful as a carrier for drug active ingredients such as siRNA and having excellent delivery efficiency even if the particle diameter has become small. SOLUTION: Provided is a lipid nanoparticle containing a cationic lipid represented by the following general formula (I) [a is an integer from 3 to 5; b is 0 or 1; R1 and R2 are each independently a group having 20 or more carbon atoms represented by the following general formula (A) (q represents an integer from 1 to 9, r represents 0 or 1, s represents an integer from 1 to 3, t represents 0 or 1, u represents an integer from 1 to 8, c represents 0 or 1, v represents an integer from 4 to 12); X represents a group represented by the following general formula (B) (d is an integer of 0 to 3, R3 and R4 are each independently a C1-4 alkyl group or a C2-4 alkenyl group) or a 5- to 7-membered non-aromatic heterocyclic group]; and a neutral lipid with a hydrophilic group having 2 or more carbon atoms and a linear hydrophobic group. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0082-0085

(2019/12/03)

BRIDGED COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS
Novel bridged compounds are disclosed herein, along with their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and methods of using such compounds as antibacterial agents. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating bacterial infections and associated diseases and conditions.
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Paragraph 00153; 00157

(2016/08/23)

Antibacterial activities of fluorescent nano assembled triphenylamine phosphonium ionic liquids
Staphylococcus aureus, a Gram positive coccal bacterium is a major cause of nosocomial infection. We report the synthesis of new triphenylamine phosphonium ionic liquids which are able to self-assemble into multiwall nanoassemblies and to reveal a strong
Brunel, Frédéric,Lautard, Christelle,Garzino, Frédéric,Giorgio, Suzanne,Raimundo, Jean M.,Bolla, Jean M.,Camplo, Michel
supporting information
p. 3770 - 3773
(2016/07/21)

Synthesis of Macrocyclic Lactones via Ring Transformation of 4-(ω-Hydroxyalkyl)-1,3-oxazol-5(4H)-ones
The synthesis of α-benzamido-α-benzyl lactones 23 of various ring size was achieved either via ‘direct amide cyclization’ by treatment of 2-benzamido-2-benzyl-ω-hydroxy-N,N-dimethylalkanamides 21 in toluene at 90 – 110° with HCl gas or by ‘ring transformation’ of 4-benzyl-4-(ω-hydroxyalkyl)-2-phenyl-1,3-oxazol-5(4H)-ones under the same conditions. The precursors were obtained by C-alkylations of 4-benzyl-2-phenyl-1,3-oxazol-5(4H)-one (15) with THP- or TBDMS-protected ω-hydroxyalkyl iodides. Ring opening of the THP-protected oxazolones by treatment with Me2NH followed by deprotection of the OH group gave the diamides 21, whereas deprotection of the TBDMS series of oxazolones 25 with TBAF followed by treatment with HCl gas led to the corresponding lactones 23 in a one-pot reaction.
Fritschi, Stephan P.,Linden, Anthony,Heimgartner, Heinz
p. 523 - 538
(2016/07/22)

Copper-catalyzed hydroalkylation of terminal alkynes
We have developed a copper-catalyzed hydroalkylation of terminal alkynes using alkyl triflates as coupling partners and (Me2HSi)2O as a hydride donor. The hydroalkylation proceeds with excellent anti-Markovnikov regioselectivity and provides exclusively (E)-alkenes. We have demonstrated that both alkyl- and aryl-substituted alkynes can be used as substrates, together with 1° alkyl and benzylic triflates. Finally, the transformation can be accomplished in the presence of a wide range of functional groups. Overall, the new hydroalkylation reaction allows highly efficient and diastereospecific synthesis of (E)-alkenes from readily available terminal alkynes and alkyl triflates. On the basis of a preliminary mechanistic study, we propose that the hydroalkylation reaction involves copper hydride formation, hydrocupration of an alkyne, and alkylation of an alkenyl copper intermediate.
Uehling, Mycah R.,Suess, Alison M.,Lalic, Gojko
supporting information
p. 1424 - 1427
(2015/02/19)

DI-SUBSTITUTED PYRIDINUM POLYMERS AND SYNTHESIS THEREOF
A method of producing a di-substituted pyridinium polymer by microwave-assisted polymerisation of a 2, 3, or 4-substituted pyridine monomer of the formula NC5R4—R′—X, wherein R is selected from hydrogen, hydroxyl, and substituted or unsubstituted alkyl, alkoxy, aryl, alkaryl, aralkyl, and alkenyl groups, R′ is a linking group, and X is a leaving group. Using this method, di-substituted pyridinium polymer compositions may be obtained wherein at least 50% of the di- substituted pyridinium polymer chains in the composition have the same degree of polymerisation.
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Page/Page column 7

(2012/05/21)

Synthesis, modification, and evaluation of (R)-de-O-methyllasiodiplodin and analogs as nonsteroidal antagonists of mineralocorticoid receptor
Macrolide (R)-de-O-methyllasiodiplodin (1), discovered to be a potent nonsteroidal antagonist of the mineralocorticoid receptor (MR), was synthesized via an efficient method and evaluated for MR antagonistic activity together with its analogs. Among all the tested compounds, compounds 18a, 18b and 18c, exhibited more potent antagonistic activity against MR with IC50 values ranging from 0.58 to 1.11 μM. Generally, it was obviously demonstrated that acetylation at phenolic hydroxyl groups and the ring size in analogs of 1 were very important for MR antagonist activity.
Jiang, Cheng-Shi,Zhou, Rong,Gong, Jing-Xu,Chen, Li-Li,Kurtán, Tibor,Shen, Xu,Guo, Yue-Wei
supporting information; experimental part
p. 1171 - 1175
(2011/04/16)

BI-FUNCTIONAL QUINOLINE ANALOGS
Provided are compounds of Formula I: wherein X is: R1 and R2 together with the phenyl to which they are bound may form a bicyclic, fused heterocyclic ring, and all other variables are as defined herein, as well as their use in treating pulmonary inflammation or bronchoconstriction and compositions comprising and processes for preparing the same.
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Paragraph 0312

(2013/03/26)

FRICTIONLESS MOLECULAR ROTARY MOTORS
A rotaxane consisting of a cucurbituril and an uncharged guest molecule, having low or null affinity therebetween is provided as well as processes for providing the same. Various uses as energy converters (“frictionless” molecular motors), biochips and biosensors using the same are also provided.
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Page/Page column 34-35

(2010/02/17)

Synthesis of the C5-C30 fragment of cyclodidemniserinol trisulfate via I2-mediated deprotection and ring closure tandem reaction
The marine natural product cyclodidemniserinol trisulfate displayed moderate HIV-1 integrase inhibitory activity. Its novel structure triggered our interest to synthesize it. In our total synthesis effort, the natural product was dissected into four fragments based on the rational retrosynthetic analysis. All four fragments were successfully prepared with orthogonal protection. And the assembly of fragment A and B furnished the C5-C30 key subunit by employing the I2-mediated deprotection and intramolecular ketal formation tandem reaction in the presence of NaHCO3 in MeCN. Our work provided flexible and practical approaches to synthesize and derive the 3,5,7-trisubstituted 6,8-dioxabicyclo [3.2.1] octane based analogs to search for new structure HIV-1 integrase inhibitors.
Liu, Jian-Hua,Jin, Yi,Long, Ya-Qiu
experimental part
p. 1267 - 1273
(2010/04/02)

Primary alkyl bromides from dimethylthiocarbamates
The conversion of primary alkyl dimethylthiocarbamates into alkyl bromides using the Vilsmeier reagent occurs in high yields in the presence of other non-acid sensitive and non-nucleophilic functional groups. Georg Thieme Verlag Stuttgart · New York.
Moynihan, Meghan F.,Tucker, Joseph W.,Abelt, Christopher J.
experimental part
p. 3565 - 3568
(2009/06/18)

Methods and compositions for treating cancer
The invention provides compounds and methods for treating cancer. Exemplary compounds are multi-functional compounds with two different moieties connected by a linker. Compounds of the invention can activate one or more pathways that result in the inhibit
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Page/Page column 10; sheet 5

(2010/02/15)

Discovery of thiochroman and chroman derivatives as pure antiestrogens and their structure-activity relationship
In order to develop pure antiestrogens, a series of 7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman and 7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman derivatives with sulfoxide containing side chains at the 4-position were designed, synthesized, and eva
Kanbe, Yoshitake,Kim, Myung-Hwa,Nishimoto, Masahiro,Ohtake, Yoshihito,Kato, Nobuaki,Tsunenari, Toshiaki,Taniguchi, Kenji,Ohizumi, Iwao,Kaiho, Shin-ichi,Morikawa, Kazumi,Jo, Jae-Chon,Lim, Hyun-Suk,Kim, Hak-Yeop
p. 4803 - 4819
(2007/10/03)

COMPOUNDS, METHODS AND FORMULATIONS FOR THE ORAL DELIVERY OF A GLUCAGON LIKE PEPTIDE (GLP)-1 COMPOUND OR AN MELANOCORTIN 4 RECEPTOR (MC4) AGONIST PEPTIDE
The present invention relates to novel compounds, methods, and formulations useful for the oral delivery of a GLP-1 compound or an MC4 agonist peptide.
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Page/Page column 13

(2008/06/13)

Metal salts of 3-methyl-chromane or thiochromane derivatives
The present invention relates to metal salts of 3-methyl-chromane or thiochromane derivatives, stereoisomers or hydrates thereof, and an anti-estrogenic pharmaceutical composition which comprises the above compound as an active component and exhibits a hi
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(2008/06/13)

Benzopyran or thiobenzopyran derivatives
The present invention provides novel benzopyran compounds, pharmaceutically acceptable salts thereof and stereoisomers thereof where the benzopyran compounds of the invention are compounds according to Formula I: The present invention further provides pharmaceutical compositions which possess anti-estrogenic activity and comprise at least one benzopyran compound of the invention and a method of treating breast cancer by administration of an effective amount of a benzopyran compound provided by the present invention.
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Page/Page column 138-139

(2010/01/31)

Methods and compositions for destruction of selected proteins
Compounds having an ansamycin anitibiotic, or other moiety which binds to hsp90, coupled to a targeting moiety which binds specifically to a protein, receptor or marker can provide effective targeted delivery of the ansamycin antibiotic leading to the deg
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Page column 5-7

(2010/02/05)

An expeditious synthesis of ostopanic acid, a plant anticancer agent
A new and stereoselective synthesis is described as an easy route to ostopanic acid using a versatile reagent: (2E,4E)-5-bromopentadienal.
Castet-Caillabet, Dominique,Ramondenc, Yvan,Pie, Gerard,Duhamel, Lucette
p. 7583 - 7588
(2007/10/03)

Zwitterionic sulfobetaine inhibitors of squalene synthase
A substantial number of sulfobetaines (e.g., 10) have been synthesized and evaluated as inhibitors of squalene synthase (SS) on the basis of the idea that their zwitterionic structure would have properties conducive both to binding in the active site and to passage through cell membranes. When the simple sulfobetaine moiety is incorporated into compounds containing hydrophobic portions like those in farnesyl diphosphate (1) or presqualene diphosphate (2), inhibition of SS in a rat liver microsomal assay was indeed observed. For example, farnesylated sulfobetaine 10 has IC50 = 10 μM and aromatic derivative 35 has IC50 = 2 μM for SS inhibition. A wide variety of structural modifications, exemplified by compounds 43, 52, 76, 85, 91, 99, 111, and 115, was investigated. Unfortunately, no inhibitors in the submicromolar range were discovered, and exploration of a different type of zwitterion seems necessary if this appealing approach to inhibition of SS is going to provide a potential antihypercholesterolemic agent.
Spencer, Thomas A.,Onofrey, Thomas J.,Cann, Reginald O.,Russel, Jonathon S.,Lee, Laura E.,Blanchard, Daniel E.,Castro, Alfredo,Gu, Peide,Jiang, Guojian,Shechter, Ishaiahu
p. 807 - 818
(2007/10/03)

Preparation of α,ω-Diols of Long Carbon Chains and Their Use in Polyurethane Synthesis
NaH promoted coupling reaction of HO(CH2)1O-TBDMS (1, TBDMS=SiMe2(t-Bu)) and Br(CH2)12O-TBDMS (2) followed by deprotection of the organosilyl groups affords HO(CH2)12O(CH2)12OH (5). 1,12-Dodecanediol reacts with an excess amount of 2 in the presence of NaH to give TBDMS-O(CH2)12O(CH2)12O(CH 2)12O-TBDMS (6) which is turned into HO(CH2)12O(CH2)12O(CH 2)12OH (7) by removal of the protecting groups. Similar 1 : 2 condensation of hydroquinone with 2 and with Br(CH2)6O-TBDMS (3) leads to formation of the corresponding α,α-diols, HO(CH2)12OC6H4O(CH2) 12OH (9) and HO(CH2)6OC6H4O(CH2) 6OH (11), respectively. The four new long α,ω-diols are isolated and characterized by means of IR and NMR spectroscopy as well as elemental analyses. Polyaddition reactions of 5, 7, 9, and 11 to 1,3-bis(isocyanatomethyl)benzene and 1,1′-methylenebis[4-isocyanatobenzene] give the corresponding poly(urethane)s in high yields. The obtained polymers, which were characterized by IR and NMR spectroscopy, have molecular weights over 20000 as determined from gel permeation chromatography using polystyrene standards.
Osakada, Kohtaro,Takenaka, Yasumasa,Yamaguchi, Isao,Yamamoto, Takakazu
p. 1477 - 1482
(2007/10/03)

Studies directed towards the total synthesis of (+)-himbacine
A convergent strategy towards himbacine (1), involving a Julia coupling between aldehyde 5 and sulfone 6 was found to be ineffective. The aldehyde 5 was synthesized via the thermal intramolecular cycloaddition of 4 with preferred formation of the endo-adduct. The Diels-Alder precursor 4 was obtained from butenolide 7, the result of a single-step condensation between the enoate derived from the (Z)-conjugated olefin 12 and 2-acetoxypropanal. In the context of the synthesis of sulfone 6 Taber's method for the synthesis of 2,6-trans-disubstituted piperidine was adapted towards a large scale synthesis of 49, a useful intermediate for the synthesis in this area.
Hofman, Sven,De Baecke, Govert,Kenda, Beno?t,De Clercq, Pierre J.
p. 479 - 489
(2007/10/03)

Restricting the flexibility of crosslinked, interfacial peptide inhibitors of HIV-1 protease
Interfacial peptides of HIV-1 protease were crosslinked with varying length alkyl-chains containing either a single cis or trans double bond, or a triple bond to remove degrees of freedom within the tethers. The synthesis of these compounds and their effects on the activity of HIV-1 protease are described.
Ulysse, Luckner G.,Chmielewski, Jean
p. 3281 - 3286
(2007/10/03)

Optical Isomers of 3,13-Dimethylheptadecane: Sex Pheromone Components of the Western False Hemlock Looper, Nepytia freemani (Lepidoptera: Geometridae)
(3S,13R)-3,13-Dimethylheptadecane [(3S,13R)-3,13-dime-17Hy] is the major pheromone component of the western false hemlock looper (WFHL), Nepytia freemani. In comparative gas chromatographic-electroantennographic detection (GC-EAD) analyses of stereoselectively synthesized isomers, 1 pg of (3S,13R)-dime-17Hy elicited significantly stronger electrophysiological responses by male WFHL antennae than did 1 pg of separately injected (3R,13R)-, (3R,13S)- or (3S,13S)-3,13-dime-17Hy. In field experiments with individually tested stereoisomers, (3S,13R)-3,13-dime-17Hy was the only stereoisomer to attract males, but the four-stereoisomer blend was 3.6 times more attractive. Quaternary and all binary combinations of (3S,13R)-3,13-dime-17Hy with the other stereoisomers were equally attractive, suggesting that synergistic behavioral activity in WFHL resided with either one of (3R,13R)-, (3R,13S)-, or (3S,13S)-3,13-dime-17Hy. Because optical isomers of (di)methylhydrocarbons do not separate on currently available columns, it remains unknown whether female WFHL also produce a four-stereoisomer pheromone blend. Substitutionality of pheromone stereoisomers without loss of behavioural activity has not previously been reported, but favorably compares with the concept of pheromone redundancy that was first suggested for the multiple pheromone component blend of the cabbage looper moth, Trichoplusia ni.
King, G. G. Skip,Gries, Regine,Gries, Gerhard,Slessor, K. N.
p. 2027 - 2046
(2007/10/03)

Mild Deprotection of tert-Butyl and tert-Amyl Ethers Leading either to Alcohols or to Trialkylsilyl ethers
Tert-butyl and tert-amyl ethers afford the corresponding tert-butyldimethylsilyl ethers when treated by one equivalent of tert-butyldimethylsilyl triflate (TBDMSOTf), followed by one equivalent of 2,6-lutidine.However, treatment by a catalytic amount of TBDMSOTf without base, led to the corresponding free alcohols.
Franck, Xavier,Figadere, Bruno,Cave, Andre
p. 711 - 714
(2007/10/02)

Design and synthesis of analogues of ionomycin
Based on the analysis of the crystal structure of the Ca2+ salt of ionomycin and the chemical and physical data on ionomycin, a number of ionomycin analogues have been synthesized to study the structural features affecting the Ca2+ binding and transport. Compounds 2, 3, and 4 were synthesized to study the effect of additional intramolecular oxygen coordination sites on Ca2+ transport. Compounds 5a-5d were prepared to study the effect of lipid solubility on Ca2+ binding and transport. Compounds 6a-6c were prepared to study the effect of the distance between the β-diketone and the carboxyl group on Ca2+ transport. A general synthetic route to these compounds has been developed. The key reactions in this route are the consecutive regioselective alkylations of the dianion of 2,4-pentanedione with the appropriate bromides.
Hu,Weiler
p. 1500 - 1511
(2007/10/02)

A new EGF-active polymeric pyridinium alkaloid from the sponge Callyspongia fibrosa
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Davies-Coleman,Faulkner,Dubowchik,Roth,Polson,Fairchild
p. 5925 - 5930
(2007/10/02)

Synthesis of β-Resorcylic Macrolides via Organopalladium Chemistry. Application to the Total Synthesis of (S)-Zearalenone
The β-resorcyclic macrolides are a class of naturally occurring 12- and 14-membered macrolides.Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest.In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct β-resorcylic macrolides.The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones.This methodology was then used to prepare (S)-zearalenone (1).
Kalivretenos, A.,Stille, J. K.,Hegedus, L. S.
p. 2883 - 2894
(2007/10/02)