611-10-9Relevant articles and documents
Highly diastereoselective mercury-mediated synthesis of functionalized 2-azabicyclo[3.3.0]octane derivatives
Pe?anha, Emerson P,Verli, Hugo,Rodrigues, Carlos R,Barreiro, Eliezer J,Fraga, Carlos A.M
, p. 1607 - 1611 (2002)
In this paper we described the synthesis of the cis-2-azabicyclo[3.3.0]octane derivative (5b) employing highly diastereoselective mercury(II)-mediated intramolecular amino-cyclization, followed by reductive demercuration of ethyl erythro-1-allyl-2-amino-1
Studies toward the diastereoselective reduction of 2-alkoxycarbonyl-2-allyl-cyclopentanone derivatives with boron hydrides
Fraga,Barreiro
, p. 1133 - 1144 (1995)
The reduction of 2-alkoxycarbonyl-2-allyl-cyclopentanone derivatives with inexpensive boron hydrides were studied showing that this process depend on chelation factors instead steric ones, affording the isomeric alcohols 2a and 3a with high diastereomeric
Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer's disease: Design, synthesis and biological evaluation
He, Qi,Liu, Jing,Lan, Jin-Shuai,Ding, Jiaoli,Sun, Yongbing,Fang, Yuanying,Jiang, Neng,Yang, Zunhua,Sun, Liyuan,Jin, Yi,Xie, Sai-Sai
supporting information, p. 512 - 528 (2018/09/29)
A series of new coumarin-dithiocarbamate hybrids were designed and synthesized as multitarget agents for the treatment of Alzheimer's disease. Most of them showed potent and clearly selective inhibition towards AChE and MAO-B. Among these compounds, compound 8f demonstrated the most potent inhibition to AChE with IC50 values of 0.0068 μM and 0.0089 μM for eeAChE and hAChE, respectively. Compound 8g was identified as the most potent inhibitor to hMAO-B, and it is also a good and balanced inhibitor to both hAChE and hMAO-B (0.114 μM for hAChE; 0.101 μM for hMAO-B). Kinetic and molecular modeling studies revealed that 8g was a dual binding site inhibitor for AChE and a competitive inhibitor for MAO-B. Further studies indicated that 8g could penetrate the BBB and exhibit no toxicity on SH-SY5Y neuroblastoma cells. More importantly, 8g did not display any acute toxicity in mice at doses up to 2500 mg/kg and could reverse the cognitive dysfunction of scopolamine-induced AD mice. Overall, these results highlighted 8g as a potential multitarget agent for AD treatment and offered a starting point for design of new multitarget AChE/MAO-B inhibitors based on dithiocarbamate scaffold.
On the ozonolysis of unsaturated tosylhydrazones as a direct approach to diazocarbonyl compounds
Fegheh-Hassanpour, Younes,Ebrahim, Faisal,Arif, Tanzeel,Sintim, Herman O.,Claridge, Timothy D. W.,Amin, Nader T.,Hodgson, David M.
, p. 2876 - 2884 (2018/05/03)
The scope and limitations are described of reacting unsaturated tosylhydrazones with O3 followed by Et3N for the generation of 1,4- and 1,5-diazocarbonyl systems. Tosylhydrazones, from tosylhydrazide condensation with readily available δ- and ?-unsaturated α-ketoesters, led in the former case to a 2-pyrazoline whereas the latter cases led to α-diazo-?-ketoesters, although a terminal alkene produced a tetrahydropyridazinol. Using the ozonolysis-Et3N strategy, tosylhydrazones from cyclic enones give 2,5- and 2,6-diazoketones with aldehyde or ester functionality at the 1-position; the α-diazoaldehydes prefer the s-trans conformation, with a rotation barrier of 74 kJ mol-1 at 25 °C determined by NMR. This one-pot ozonolysis/Bamford-Stevens chemistry demonstrates both the tolerance of tosylhydrazones to ozone, and the subsequently added amine playing a dual role to directly transform the intermediate tosylhydrazone ozonides into products containing reactive diazo and ketone functionalities; such adducts are of particular value as precursors to cyclic carbonyl ylides for 1,3-dipolar cycloadditions.
1-(Arylmethyl)-5,6,7,8-tetrahydroquinazolline-2,4-diones and Analogs and the Use Thereof
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Paragraph 0151; 0199, (2014/09/30)
Disclosed are novel 1-(arylmethyl)-5,6,7,8-tetrahydroquinazoline-2,4-diones and analogs thereof, represented by the Formula I, wherein Ar, A, B, R3-R6 are defined herein. Compounds having Formula I are PARP inhibitors. Therefore, compounds of the invention may be used to treat clinical conditions that are responsive to the inhibition of PARP activity, such as cancer.
Phosphate tricyclic coumarin analogs as steroid sulfatase inhibitors: Synthesis and biological activity
Kozak, Witold,Dasko, Mateusz,Maslyk, Maciej,Pieczykolan, Jerzy S.,Gielniewski, Bartlomiej,Rachon, Janusz,Demkowicz, Sebastian
, p. 44350 - 44358 (2014/12/10)
In the present work, we report convenient methods for the synthesis and biological evaluation of phosphate tricyclic coumarin derivatives as potential steroid sulfatase inhibitors. The described synthesis includes the straightforward preparation of 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one, 3-hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-8,9,10,11-tetrahydro-7H-cyclohepta[c]chromen-6-one modified with various phosphate moieties. The inhibitory effects of the synthesized compounds were tested on STS isolated from human placenta as well as the MCF-7, MDA-MB-231 and MDA-MB-435S cancer cell lines. Most of the new STS inhibitors possessed IC50 values between 21 to 159 μM. In the course of our investigation, the largest inhibitory effects in the STS enzyme assays were observed for the three compounds 9p, 9r and 9s, with IC50 values of 36.4, 37.8 and 21.5 μM, respectively (IC50 value of 1.0 μM for the 665-COUMATE used as a reference). The compound 9r, exhibited the highest potency against MCF-7, an estrogen receptor positive (ER+) cell line, with a GI50 value of 24.7 μM. The structure-activity relationships of the synthesized coumarin derivatives with the STS enzyme are discussed.
1-(ARYLMETHYL)-5,6,7,8-TETRAHYDROQUINAZOLINE-2,4-DIONES AND ANALOGS AND THE USE THEREOF
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Page/Page column 23; 33, (2013/05/22)
Disclosed are novel 1-(arylmethyl)-5,6,7,8-tetrahydroquinazoline-2,4-diones and analogs thereof, represented by the Formula I, wherein Ar, A, B, R3-R6 are defined herein. Compounds having Formula I are PARP inhibitors. Therefore, compounds of the invention may be used to treat clinical conditions that are responsive to the inhibition of PARP activity, such as cancer.
Synthesis of five-and six-membered 1,3,3-trimethyl-2-(trimethylsilyl) cycloalkenes: A novel preparation of alkyl/alkenyl/aryl 2,5,5-trimethyl-1- cyclopentenyl ketones
Venkatesha, Manjunatha A.,Suresh, Hariprasad
, p. 759-768+S57-S61 (2013/07/26)
1,3,3-trimethyl-2-(trimethylsilyl)cyclopentene and 1,3,3-trimethyl-2- -(trimethylsilyl)cyclohexene were prepared in good yields by the Wurtz-Fittig coupling reaction of the corresponding 2-iodo-1,3,3-trimethylcyclopentene and 2-chloro-1,3,3-trimethylcyclohexene with metallic sodium and chlorotrimethylsilane in anhydrous ether solvent. The Friedel-Crafts acylation reaction of 1,3,3-trimethyl-2-(trimethylsilyl)cyclopentene with six different acid chlorides and the novel preparation of six alkyl/alkenyl/aryl 2,5,5-trimethyl-1-cyclopentenyl ketones are reported.
2-METHYLENE-5-SUBSTITUTED-METHYLENECYCLOPENTANONE DERIVATIVES AND USE THEREOF
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Page/Page column 12, (2011/04/18)
The invention relates to 2-methylene-5-substituted-methylenecyclopentanone derivatives of formula I, and the use thereof. The derivatives of formula I as active components are useful for preparing a medicine for the treatment and/or prevention of cancer diseases such as breast cancer, lung cancer, colon cancer, rectal cancer, stomach cancer, prostate cancer, bladder cancer, uterus cancer, pancreatic cancer and ovary cancer. The active compounds of the invention may be used as an anticancer drug alone or used in combination with one or more other antitumor drugs. A combined therapy can be carried out by administrating each therapeutic component concurrently, subsequently or separately.
2-METHYLENE-5-SUBSTITUTED METHYLENE CYCLOPENTANONE DERIVATIVES AND USE THEREOF
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Page/Page column 16-17, (2010/11/19)
The invention relates to 2-methylene-5-substituted-methylenecyclopentanone derivatives of formula I, and the use thereof. The derivatives of formula I as active components are useful for preparing a medicine for the treatment and/or prevention of cancer diseases such as breast cancer, lung cancer, colon cancer, rectal cancer, stomach cancer, prostate cancer, bladder cancer, uterus cancer, pancreatic cancer and ovary cancer. The active compounds of the invention may be used as an anticancer drug alone or used in combination with one or more other antitumor drugs. A combined therapy can be carried out by administrating each therapeutic component concurrently, subsequently or separately.
