cas 60032-63-5, 3-IODO-4-HYDROXYBENZALDEHYDE

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Synthesis and radioiodination of some daunorubicin and doxorubicin derivatives
Daunorubicin and doxorubicin are efficient agents for cancer treatment. Their clinical efficacy is, however, hampered by their indiscriminant toxicity. This problem may be circumvented by encapsulating the drugs in liposomes and selectively targeting the tumor cells using tumor targeting agents. Furthermore, the antitumor effect could be enhanced by attaching the Auger electron emitter, 125I, to daunorubicin and doxorubicin derivatives. In this context a number of ester, amide, and amine derivatives of daunorubicin and doxorubicin were synthesized. Benzoic acid ester derivatives of daunorubicin were synthesized by nucleophilic esterification of the 14-bromodaunorubicin with the potassium salt of the corresponding benzoic acid, resulting in good yields. Nicotinic acids and benzoic acids, activated with a succinimidyl group, were coupled to the amino group of daunorubicin to give the corresponding amide derivatives. Amine derivatives were obtained by the reductive amination of aromatic aldehydes with daunorubicin hydrochloride. The stannylated ester and amide derivatives were used as precursors for radioiodination. Radiolabeling with 125I was performed using chloramine-T as an oxidant. The optimized labeling resulted in high radiolabeling yields (85-95%) of the radioiodinated daunorubicin and doxorubicin derivatives. Radioiodination of the amines was conducted at the ortho position of the activated phenyl rings providing moderate radiochemical yields (55-75%).
Ghirmai, Senait,Mume, Eskender,Tolmachev, Vladimir,Sj?berg, Stefan
p. 15 - 24
(2005)
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Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate
Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene gives practical yields only in dichloromethane. In the case of thiophene and N -acetyl- p -toluidine, electrophilic iodination is accompanied by a small extent of chlorination.
Hussain, Anwar,Sarkar, Akash Mamon,Sereda, Grigoriy,Zefirov, Nikolai
p. 1140 - 1146
(2020/04/01)

Alpha-Cyano-4-Hydroxy-3-Iodocinnamic Acid as a Matrix in Maldi Mass Spectrometry
A heavy-atom derivative of CHCA, a primary matrix molecule for matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS), is synthesized and purified. This new matrix molecule α-cyano-4-hydroxy-3-iodocinnamic acid (CHICA) is characterized by 1H NMR and mass spectrometry. CHICA is shown to increase MALDI-MS yield for the test analytes human angiotensin II and sex pheromone inhibitor as compared to both CHCA and an alternative heavy-atom CHCA derivative matrix. An optimal CHICA matrix concentration is determined to be 4 mg/mL. Analyte ion yield is shown to be comparable for CHICA and CHCA for analyte concentrations below 0.001 mg/mL. For analyte concentrations above this threshold, use of CHICA resulted in higher analyte yield and significantly lower relative standard deviation.
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Paragraph 0077

(2019/06/15)

Synthesis and cycloaddition reactions of strained alkynes derived from 2,2′-dihydroxy-1,1′-biaryls
A series of strained alkynes, based on the 2,2′-dihydroxy-1,1′-biaryl structure, were prepared in a short sequence from readily-available starting materials. These compounds can be readily converted into further derivatives including examples containing fluorescent groups with potential for use as labelling reagents. The alkynes are able to react in cycloadditions with a range of azides without the requirement for a copper catalyst, in clean reactions with no observable side reactions.
Mistry, Anish,Knighton, Richard C.,Forshaw, Sam,Dualeh, Zakaria,Parker, Jeremy S.,Wills, Martin
supporting information
p. 8965 - 8975
(2018/12/10)

Ultrasonically assisted halogenation of aromatic compounds using isoquinolinium bound hypervalent chromium and tetrabutylammonium halides in PEG-600 solutions under acid free and solvent-free conditions
Isoquinolinium bound Cr(VI) reagents like isoquinolinium dichromate (IQDC) and isoquinolinium chlorochromate (IQCC) have been successfully accomplished as efficient reagents for oxidative halogenation of aromatic compounds using tetrabutylammonium halide (TBAX) as halogenating agents in aqueous polyethylene glycol (PEG-600) under acid free conditions. Tetrabutylammonium bromide (TBAB) has been used for bromination and tetrabutylammonium iodide (TBAI) for iodination. The halogenation reactions that occurred smoothly in 2 to 7 h under conventional conditions are accelerated magnificently under sonication with few minutes (25 to 70 min) of reaction time and fairly good yields. The reactions occurred at moderate temperature under mild and environmentally safe conditions with simple work up.
Sambashiva Rao,Ramesh, Kola,Rajanna,Chakrvarthi
p. 1892 - 1896
(2018/07/10)

P2X3 AND/OR P2X2/3 COMPOUNDS AND METHODS
The present disclosure provides novel compounds and methods for preparing and using these compounds. In one embodiment, the compounds are of the structure of formula (I), wherein R1-R7 are defined herein. In a further embodiment, these compounds are useful in method for regulating one or both of the P2X3 or P2X2/3 receptors. In another embodiment, these compounds are useful for treating pain in patients by administering one or more of the compounds to a patient. In another embodiment, these compounds are useful for treating respiratory dysfunction in patients by administering one or more of the compounds to a patient.
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Paragraph 0221-0224

(2018/04/17)

A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine
Two consecutive Cu-catalyzed Ullmann-type C-O couplings permitted the first successful entry toward the curare alkaloids (±)-tubocurine and (±)-curine. Starting from vanillin, the synthetic sequence comprises 15 linear steps and includes a total of 24 transformations. In addition, the total synthesis of tubocurine represents a formal total synthesis of the famous arrow poison alkaloid tubocurarine.
Otto, Nicola,Ferenc, Dorota,Opatz, Till
p. 1205 - 1217
(2018/06/18)

Isoquinolinium Dichromate and Chlorochromate as Efficient Catalysts for Oxidative Halogenation of Aromatic Compounds under Acid-Free Conditions
Isoquinolinium dichromate and isoquinolinium chlorochromate were found as efficient catalysts to trigger oxidative bromination and iodination of aromatic hydrocarbons with KBr/KI and KHSO4 under acid-free conditions. Reaction times reduced highly significantly under sonication, followed by corresponding mono bromo derivatives in very good yield with high regioselectivity.
Rao, A. Sambashiva,Rajanna,Reddy, K. Rajendar,Kulkarni, Subhash
p. 832 - 837
(2016/02/12)

Benzocarbazoles dioxane derivatives, its preparation process and its use in medicine
The invention relates to a benzodioxane derivative, a preparation method thereof and application of the derivative in medicines. Specifically, the invention relates to a novel benzodioxane derivative shown as a formula (I), medial salt thereof or a medicine composition containing the derivative, and a preparation method of the derivative. The invention further relates to a use of the benzodioxane derivative and the medial salt thereof or the medicine composition containing the derivative in preparing therapeutic agent, especially GPR 40 agonist, and a drug for treating the diseases such as diabetes, metabolic disorders and the like, wherein each substituent group in the formula (I) is as defined in the description.
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Paragraph 0630; 0632-0635

(2016/10/10)

Harnessing reversible oxidative addition: Application of diiodinated aromatic compounds in the carboiodination process
An I for an I: Conditions for the intramolecular carboiodination and the simultaneous convergent intramolecular carboiodination/intermolecular Heck reaction of various diiodoarenes were developed. The ability of the Pd 0/QPhos catalyst/ligand combination to undergo reversible oxidative addition allows these reactions to proceed well, thus increasing both the appeal and utility of this class of substrates in site-selective cross-coupling reactions. Copyright
Petrone, David A.,Lischka, Matthias,Lautens, Mark
p. 10635 - 10638
(2013/10/21)

2,2′-biphenols via protecting group-free thermal or microwave-accelerated suzuki-miyaura coupling in water
User-friendly protocols for the protecting group-free synthesis of 2,2′-biphenols via Suzuki-Miyaura coupling of o-halophenols and o-boronophenol are presented. The reactions proceed in water in the presence of simple additives such as K2CO3, KOH, KF, or TBAF and with commercially available Pd/C as precatalyst. Expensive or laboriously synthesized ligands or other additives are not required. In the case of bromophenols, efficient rate acceleration and short reaction times were accomplished by microwave irradiation.
Schmidt, Bernd,Riemer, Martin,Karras, Manfred
p. 8680 - 8688
(2013/09/24)

TREATMENT OF DISEASES BY EPIGENETIC REGULATION
The present disclosure provides non-naturally occurring polyphenol compounds that inhibit the bromodomain and extra terminal domain (BET) proteins. The disclosed compositions and methods can be used for treatment and prevention of diseases or disorders that are susceptible to administration of a BET inhibitor.
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Paragraph 0458; 0459

(2013/11/05)

Topical anti-inflammatory activity of boropinic acid and its natural and semi-synthetic derivatives
Boropinic acid is a natural isopentenyloxycinnamic acid extracted from the aerial parts of Boronia pinnata Sm. (Rutaceae) with soybean 5-lipoxygenase inhibitory activity. In this paper the topical anti-inflammatory activity of boropinic acid and some of its natural and semi-synthetic derivatives was evaluated using the Croton oil ear test in mice as a model of acute inflammation. Some of the tested compounds (15, 17, 19, 20) revealed an effect comparable (ID50 = 0.18 ÷ 0.72 μmol/cm2) to that of the reference drug indomethacin (ID50 = 0.23 μmol/cm 2), a non-steroidal anti-inflammatory drug.
Epifano, Francesco,Sosa, Silvio,Tubaro, Aurelia,Marcotullio, M. Carla,Curini, Massimo,Genovese, Salvatore
supporting information; experimental part
p. 769 - 772
(2011/03/18)

Green and efficient method for the iodination of phenols in water
In this article, green conversion of phenols to the corresponding iodide derivatives is reported. The reactions were conducted in water, using potassium iodide as the source of iodine and potassium ferrate as the oxidizing agent. The selected phenols were successfully iodinated in good to excellent yields in mild and non-toxic reaction conditions. Copyright Taylor & Francis Group, LLC.
Tajik, Hassan,Dadras, Akbar,Hosseini, Abolfazl
experimental part
p. 258 - 261
(2011/06/26)

Fused Thiazole Derivatives As Kinase Inhibitors
A series of 6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5H)-one derivatives, which are substituted in the 2-position by a substituted morpholin-4-yl moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.
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Page/Page column 13

(2011/01/12)

A mild and simple iodination of phenols with trichloroisocyanuric acid/I2/wet SiO2 system
Molecular iodine in the presence of trichloroisocyanuric acid and wet sio2 has been utilized efficiently for iodination of phenols under mild reaction conditions.
Akhlaghinia, Batool,Rahmani, Marzieh
experimental part
p. 3 - 6
(2010/08/19)

Ecofriendly iodination of activated aromatics and coumarins using potassium iodide and ammonium peroxodisulfate
An environmentally benign protocol for the iodination of activated aromatics, such as phenols, anilines, and hydroxycou-marins, using inexpensive commercially available potassium iodide and ammonium peroxodisulfate (1:2.5 molar equivalents per mole of substrate) in aqueous methanol (MeOH-H 2O, 6:1) at room temperature has been developed. The protocol provides for ortho-selective monoiodination as the predominant product without added acid and it is compatible with a number of common oxidizible functional groups, such as formyl, benzylic C-H, aromatic amines and hydroxymethyl. Good to acceptable yields of monoiodinated products in acceptable reaction times and exclusive ortho-iodination for 7-hydroxycoumarins, despite the presence of vinylogous electronrich C3, are some of the key advantageous features of the method. Georg Thieme Verlag Stuttgart.
Ganguly, Nemai C.,Barik, Sujoy Kumar,Dutta, Sanjoy
experimental part
p. 1467 - 1472
(2010/09/16)

NOVEL ANTI-INFLAMMATORY AGENTS
Disclosed are methods of regulating interleukin-6 (IL-6) and/or vascular cell adhesion molecule-1 (VCAM-1) and methods of treating and/or preventing cardiovascular and inflammatory diseases and related disease states, such as, for example, atherosclerosis, asthma, arthritis, cancer, multiple sclerosis, psoriasis, and inflammatory bowel diseases, and autoimmune disease(s) by administering a naturally occurring or synthetic quinazolone derivative. The invention provides novel synthetic quinazolone compounds, as well as pharmaceutical compositions comprising those compounds.
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Page/Page column 89-90

(2010/11/05)

Total synthesis of 3′,3?-binaringenin and related biflavonoids
The synthesis of natural 3++,3?-binaringenin and four related biflavonoids was performed in good overall yield (15-35%) starting from readily available phloroglucinol and 4-hydroxy- or 4-methoxybenzaldehyde. Preliminary results indicate that some of these compounds have an interesting activity against S. aureus. Georg Thieme Verlag Stuttgart.
Sagrera, Gabriel,Seoane, Gustavo
supporting information; experimental part
p. 2776 - 2786
(2010/10/19)

FUSED THIAZOLE DERIVATIVES AS KINASE INHIBITORS
A series of 6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5H)-one derivatives, which are substituted in the 2-position by a substituted morpholin-4-yl moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.
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Page/Page column 36

(2009/03/07)

A new drug-release method using the Staudinger ligation
Many drugs induce severe side-effects caused by their lack of selectivity. One way to overcome this problem is to design a specific system which releases a free drug in a controlled manner. Herein we describe a new way to liberate a drug from a prodrug using the Staudinger ligation as the trigger.
Azoulay, Michel,Tuffin, Gerald,Sallem, Wafa,Florent, Jean-Claude
p. 3147 - 3149
(2007/10/03)

Syntheses and radical scavenging activities of resveratrol derivatives
Nine new resveratrol derivatives, having bromo, iodo, and fluoroethyl groups, were designed and synthesized. All compounds having free phenol groups showed good free radical scavenging activity. Among them, 2-bromoresveratrol 19 has a similar free radical scavenging activity to (+)-catechin.
Lee, Hyun Jung,Seo, Jai Woong,Lee, Bong Ho,Chung, Kyoo-Hyun,Chi, Dae Yoon
p. 463 - 466
(2007/10/03)

Iodination of aromatic compounds under mild and solvent-free conditions
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Hajipour, Abdol R.,Ruoho, Arnold E.
p. 647 - 651
(2007/10/03)

Tetramethylammonium dichloroiodate: An efficient and environmentally friendly iodination reagent for iodination of aromatic compounds under mild and solvent-free conditions
Tetramethylammonium dichloroiodate (1, TMADCI) as a mild and efficient iodination reagent was prepared. Iodination of different aromatic compounds with this reagent takes place fast and with high yields under solvent-free conditions.
Hajipour, Abdol R.,Arbabian, Marty,Ruoho, Arnold E.
p. 8622 - 8624
(2007/10/03)

Sulfonamidopyrrolidinone factor Xa inhibitors: Potency and selectivity enhancements via P-1 and P-4 optimization
Sulfonamidopyrrolidinones were previously disclosed as a selective class of factor Xa (fXa) inhibitors, culminating in the identification of RPR120844 as a potent member with efficacy in vivo. Recognizing the usefulness of the central pyrrolidinone template for the presentation of ligands to the S-1 and S-4 subsites of fXa, studies to optimize the P-1 and P-4 groups were initiated. Sulfonamidopyrrolidinones containing 4-hydroxy- and 4- aminobenzamidines were discovered to be effective inhibitors of fXa. X-ray crystallographic experiments in trypsin and molecular modeling studies suggest that our inhibitors bind by insertion of the 4-hydroxybenzamidine moiety into the S-1 subsite of the fXa active site. Of the P-4 groups examined, the pyridylthienyl sulfonamides were found to confer excellent potency and selectivity especially in combination with 4-hydroxybenzamidine. Compound 20b (RPR130737) was shown to be a potent fXa inhibitor (K1 = 2 nM) with selectivity against structurally related serine proteinases (> 1000 times). Preliminary biological evaluation demonstrates the effectiveness of this inhibitor in common assays of thrombosis in vitro (e.g. activated partial thromboplastin time) and in vivo (e.g. rat FeCl2-induced carotid artery thrombosis model).
Choi-Sledeski, Yong Mi,McGarry, Daniel G.,Green, Daniel M.,Mason, Helen J.,Becker, Michael R.,Davis, Roderick S.,Ewing, William R.,Dankulich, William P.,Manetta, Vincent E.,Morris, Robert L.,Spada, Alfred P.,Cheney, Daniel L.,Brown, Karen D.,Colussi, Dennis J.,Valeria, Chu,Heran, Christopher L.,Morgan, Suzanne R.,Bentley, Ross G.,Leadley, Robert J.,Maignan, Sebastien,Guilloteau, Jean-Pierre,Dunwiddie, Christopher T.,Pauls, Henry W.
p. 3572 - 3587
(2007/10/03)

A concise synthesis of thyroxine (T4) and 3,5,3'-Triiodo-L-thyronine (T3)
The mono- and di-iodo derivatives of 1-oxaspiro[2,5]bicycloocta-4,7-dien-6-one, 8 and 9, reacted readily with 3,5-diiodo-L-tyrosine at pH 8.0 to give 3,5,3'-triiodo-L-thyronine (T3) and thyroxine in 70% and 94% yields respectively. In turn, 8 and 9 were prepared by the sodium bismuthate oxidation of their corresponding iodinated p-hydroxybenzyl alcohol derivatives, 6 and 7 in 32% and 37% yields.
Salamonczyk, Grzegorz M.,Oza, Vibha B.,Sih, Charles J.
p. 6965 - 6968
(2007/10/03)

[125I/127I]iodoHoechst 33342: synthesis, DNA binding, and biodistribution.
An iodinated analog of the DNA-minor-groove-binding agent Hoechst 33342 has been synthesized and evaluated for DNA binding and tumor targeting. The bis-benzimidazole ring system of the title compound was constructed from the piperazinyl terminus via a Pinner-type cyclization followed by oxidative cyclization of the diamine Schiff base. To synthesize radioiodoHoechst 33342, (trimethylstannyl)Hoechst 33342 was prepared by the same strategy and subjected to mild radioiododestannylation in the presence of lactoperoxidase. After purification by HPLC, the radiochemical was separated in carrier-free form with > 85% radiochemical yield and > 99% chemical and radiochemical purity. Fluorescence spectrometric analysis of the binding of iodoHoechst 33342 to calf thymus DNA gave an equilibrium association constant (Ka) of 2.57 x 10(7) M-1 comparable to the Ka value of Hoechst 33342. Fluorescence microscopy of viable V79 cells demonstrated that the iodinated dye stained the nuclei with avidity similar to that of the noniodinated dye. The biodistribution of [125I]-iodoHoechst 33342 in LS174T tumor-bearing athymic mice 4 h postadministration showed a tumor uptake of 3-4% injected dose per gram (ID/g), tumor/blood ratio of 6-8, and tumor/ nontumor ratios above unity for most organs. A low thyroid uptake (approximately 2% ID/g) indicated that the radiochemical did not deiodinate and was stable in vivo.
Harapanhalli,McLaughlin,Howell,Rao,Adelstein,Kassis
p. 4804 - 4809
(2007/10/03)

New Synthetic Applications of Water-Soluble Acetate Pd/TPPTS Catalyst Generated in Situ. Evidence for a True Pd(0) Species Intermediate
Studies on the sp-sp intermolecular coupling reactions with the palladium water-soluble catalyst prepared in situ from palladium(II) acetate and sulfonated triphenylphosphine P(C6H4-m-SO3Na)3 (TPPTS) in a homogeneous acetonitrile-water system, without Cu(I) promotor, afford diynes with moderate yields (45-65percent).Under the same conditions, the sp2-sp coupling of 2-iodophenols or 2-iodoanilines and terminal alkynes followed by intramolecular cyclization gives indolic and furanic products in good yields (60-99percent).Under these aqueous conditions, an efficient and short synthesis of eutypine illustrated the synthetic potentiality of the coupling.Furthermore, through a series of kinetic and 31P NMR experiments, we have demonstrated that a mixture of Pd(OAc)2 and TPPTS affords spontaneously a palladium(0) complex, through formation of bivalent complex Pd(OAc)2(TPPTS)2.A detailed mechanism of the reaction has been investigated thoroughly and the pertinent rate constants measured.The resulting palladium(0) complex reacts with phenyl iodide via an oxidative addition.This complex is considerably less reactive than the corresponding complex generated from PPh3, probably due to steric effects.
Amatore, Christian,Blart, Errol,Genet, Jean Pierre,Jutand, Anny,Lemaire-Audoire, Sandrine,Savignac, Monique
p. 6829 - 6839
(2007/10/03)

The Synthesis of Natural Acetylenic Compounds from Eutypa lata (Pers:F.) TUL.
The synthesis of a series of novel acetylenic compounds 1-7, isolated recently from the fungus Eutypa lata, is described.The crucial step is the coupling reaction between protected aryl halogenide and the acetylenic chain as a cuprous acetylide (Scheme I).A more efficient method using bis(triphenylphosphine)palladium dichloride () as catalyst was also carried out with success.
Defranq, Eric,Zesiger, Thierry,Tabacchi, Raffaele
p. 425 - 430
(2007/10/02)