cas 27640-33-1, (S)-(+)-2-INDOLINEMETHANOL

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SYNTHESIS OF PYRROLIZIDINES AND RELATED COMPOUNDS BY ALDOL CYCLIZATION OF N--α-AMINOALDEHYDES
Treatment of 1--2-pyrrolidinecarbaldehyde with sodium hydride in tetrahydrofuran (THF) gave the aldol condensation product, 5,6,7,7a-tetrahydro-2-methylthio-3H-pyrrolizin-3-one.However, when the same aldehyde was treated with sodium hydroxide in aqueous THF, 5,6,7,7a-tetrahydro-7a-hydroxy-3-methylthio-3H-pyrrolizin-3-one was obtained.These reactions were applied to the synthesis of indolizidine and pyrroloindole derivatives.
Ikeda, Masazumi,Harada, Suzumi,Yamasaki, Atsuko,Kinouchi, Katsuko,Ishibashi, Hiroyuki
p. 943 - 954
(1988)
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CHIRAL PHOSPHORAMIDITE AUXILIARIES AND METHODS OF THEIR USE
Disclosed are P-stereogenic groups that may be used in the synthesis of compounds including stereochemically enriched P-stereogenic phosphorothioates. P-stereogenic groups may be provided in nucleoside phosphoramidites including a sugar bonded to a nucleobase and to a stereochemically enriched phosphoramidite as well as methods of their use and methods of making them.
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(2019/01/16)

Design and synthesis of novel indoline-(thio)urea hybrids
A series of novel indoline-(thio)urea were designed and prepared using indoline(s) as a new platform and tested as organocatalysts in the Michael and Morita–Baylis–Hillman reactions. Most of the compounds were found to be very active catalysts although they did not promote the enantioselectivity. As agents for the conversion of thiocarbonyl compounds into carbonyl compounds, potentials of PIFA and DDQ were also displayed. Furthermore, DFT calculations rationalized the experimentally observed non-enantioselectivity of the catalysts.
Lafzi, Ferruh,Kilic, Haydar,Tanriver, Gamze,Avc?, ?yküm Naz,Catak, Saron,Saracoglu, Nurullah
supporting information
p. 3510 - 3527
(2019/11/14)

FUSED THIAZOLOPYRIMIDINE DERIVATIVES AS MNKS INHIBITORS
The present invention relates to compounds of formulae I and H, or pharmaceutically acceptable salts or esters thereof. Further aspects of the invention relate to pharmaceutical compositions and therapeutic uses of said compounds in the treatment of diseases of uncontrolled cell growth, proliferation and/or survival, inappropriate cellular immune responses, inappropriate cellular inflammatory responses, or neurodegenerative disorders, preferably tauopathies, even more preferably, Alzheimer's disease.
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Page/Page column 71

(2017/06/12)

Enantioselective Synthesis of 2-Bromomethyl Indolines via BINAP(S)-Catalyzed Bromoaminocyclization of Allyl Aniline
An enantioselective bromoamination of allyl aniline with N-bromosuccinimide (NBS) catalyzed by BINAP(S) (BINAP monosulfide) is described. This protocol could provide a range of chiral 2-bromomethyl indolines in good to excellent yields with up to 87% ee.
Yu, Sheng-Nan,Li, Yin-Long,Deng, Jun
p. 2499 - 2508
(2017/07/22)

Green Organocatalytic Synthesis of Indolines and Pyrrolidines from Alkenes
Employing a green and efficient 2,2,2-trifluoroacetophenone-catalyzed oxidation of alkenes, which utilizes H2O2 as the green oxidant, a novel and sustainable synthesis of indolines and pyrrolidines was developed. This constitutes a cheap, general and environmentally-friendly protocol for the synthesis of substituted nitrogen-containing heterocycles. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated leading to the desired nitrogen heterocycles in good to excellent yields. (Figure presented.).
Theodorou, Alexis,Kokotos, Christoforos G.
p. 1577 - 1581
(2017/05/05)

Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst
The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
Murray, James I.,Flodén, Nils J.,Bauer, Adriano,Fessner, Nico D.,Dunklemann, Daniel L.,Bob-Egbe, Opetoritse,Rzepa, Henry S.,Bürgi, Thomas,Richardson, Jeffery,Spivey, Alan C.
supporting information
p. 5760 - 5764
(2017/05/12)

Asymmetric Hydrogenation of Unprotected Indoles Catalyzed by η6-Arene/N-Me-sulfonyldiamine-Ru(II) Complexes
Protecting-group-free transformation is a challenging and important issue in atom-economical organic synthesis. The η6-arene/N-Me-sulfonyldiamine-Ru(II)-BF4 complex-catalyzed asymmetric hydrogenation of 2-substituted unprotected indoles in weakly acidic hexafluoroisopropanol gives optically active indoline compounds with up to >99% ee. Under mild reaction media, halogen atoms and synthetically important protecting groups (e.g., silyl ether, acetal, benzyl ether, and ester) on indoles are maintained, which is advantageous for the synthesis of further complex indoline molecules.
Touge, Taichiro,Arai, Takayoshi
supporting information
p. 11299 - 11305
(2016/10/12)

MORPHOLINO COMPOUNDS, USES AND METHODS
The invention relates to morpholino-derivatives according to Formula (I) or stereoisomers or pharmaceutically acceptable salts or solvate thereof, wherein R1, R2, R3, R4, R5, R6, R7/s
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Paragraph 0333-0335

(2014/06/11)

Design, synthesis, and biological activities of novel hexahydropyrazino[1, 2-a]indole derivatives as potent inhibitors of apoptosis (IAP) proteins antagonists with improved membrane permeability across MDR1 expressing cells
We previously reported octahydropyrrolo[1,2-a]pyrazine derivative 2 (T-3256336) as a potent antagonist for inhibitors of apoptosis (IAP) proteins. Because compound 2 was susceptible to MDR1 mediated efflux, we developed another scaffold, hexahydropyrazino[1,2-a]indole, using structure-based drug design. The fused benzene ring of this scaffold was aimed at increasing the lipophilicity and decreasing the basicity of the scaffold to improve the membrane permeability across MDR1 expressing cells. We established a chiral pool synthetic route to yield the desired tricyclic chiral isomers. Chemical modification of the core scaffold led to a representative compound 50, which showed strong inhibition of IAP binding (X chromosome-linked IAP [XIAP]: IC 50 23 nM and cellular IAP [cIAP]: IC50 1.1 nM) and cell growth inhibition (MDA-MB-231 cells: GI50 2.8 nM) with high permeability and low potential of MDR1 substrate.
Shiokawa, Zenyu,Hashimoto, Kentaro,Saito, Bunnai,Oguro, Yuya,Sumi, Hiroyuki,Yabuki, Masato,Yoshimatsu, Mie,Kosugi, Yohei,Debori, Yasuyuki,Morishita, Nao,Dougan, Douglas R.,Snell, Gyorgy P.,Yoshida, Sei,Ishikawa, Tomoyasu
p. 7938 - 7954
(2014/01/06)

MORPHOLINO COMPOUNDS, USES AND METHODS
The invention relates to morpholino-derivatives according to Formula (I) or stereoisomers or pharmaceutically acceptable salts or solvate thereof, wherein R1, R2, R3, R4, R5, R6, R7/s
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Page/Page column 70-71

(2012/12/13)

Hexafluoroisopropanol: A powerful solvent for the hydrogenation of indole derivatives. Selective access to tetrahydroindoles or cis-fused octahydroindoles
Pd/C in HFIP was used to hydrogenate indole derivatives under relatively mild conditions, leading to potential synthetic intermediates of bioactive compounds. Depending on their substitution, tetrahydroindoles or octahydroindoles could selectively be obtained.
Clarisse, Damien,Fenet, Bernard,Fache, Fabienne
experimental part
p. 6587 - 6594
(2012/09/08)

Substituted Spiroamine Compounds
Substituted spiroamine compounds corresponding to the formula (I) In which m, n, o, p, Q, r, s, t, R1, R2, R3, R4a, R4b, R5a, R5b, R6a, R6b, R7, R8, R9, R10 and R11 have defined meanings; a process for the preparation of such compounds, pharmaceutical compositions containing such compounds and the use of substituted spiroamines for the treatment or inhibition of pain and/or other conditions mediated by the bradykinin 1 receptor.
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(2010/05/13)

SUBSTITUTED SULFONAMIDE DERIVATIVES
The invention relates to substituted sulfonamide derivatives, processes for the preparation thereof, medicaments containing these compounds and the use of substituted sulfonamide derivatives for the preparation of medicaments.
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Page/Page column 69-70

(2009/10/22)

Synthesis of novel (3a,S)-1-aryl/aryloxy/alkoxy-3a,4-dihydro-3H-1λ5- [1,3,2]oxazaphospholo [3,4-a] indole-1-ones, thiones, and selenones
Synthesis of novel (3a,S)-1-aryl/aryloxy/alkoxy-3a,4-dihydro-3H-1λ5- [1,3,2]oxazaphospholo [3,4-a] indole-1-ones, thiones, and selenones was achieved in two steps with high yields from 2,3-dihydro-1H-indol-2(S)yl methanol (1) and dichlorophenyl phosphine/ethyl dichlorophosphite (2a and b) in the presence of triethylamine in dry THF followed by treatment with hydrogen peroxide, sulfur, and selenium. The compounds 4g-k have been synthesized by the direct cyclocondensation of 1 with different substituted phenyl phosphorodichloridates (2c-e, g) and bis(2-chloroethyl) phosphoramidic dichloride (2f). Copyright Taylor & Francis Group, LLC.
Babu, B. Hari,Prasad, G. Syam,Raju, C. Naga,Reddy, C. Suresh
p. 1398 - 1406
(2008/09/20)

Kinetic resolutions of lndolines by a nonenzymatic acylation catalyst
The first method for the kinetic resolution of indolines through catalytic N-acylation is described. To improve the selectivity factor, new planar-chiral PPY-derived catalysts were synthesized, wherein the chiral environment was systematically modified. This work provides a rare example of a nonenzyme-based acylation catalyst for the kinetic resolution of amines. Copyright
Arp, Forrest O.,Fu, Gregory C.
p. 14264 - 14265
(2008/03/13)

Dual enantioselective Diels-Alder process in the cyclization of chiral acrylamide with dienes
Diels-Alder cycloadditions of chiral acrylamides with cyclopentadiene or 2, 3-dimethyl butadiene proceed with high diastereofacial selectivity. Either endo-R or endo-S products have been obtained depending upon the structures of acrylamides and Lewis acids used. The endo form was exclusively obtained over the exo form. The dependence of the mechanism of formation of opposite configurations of endo-R or endo-S products on the Lewis acids is discussed. Copyright 2004 John Wiley & Sons, Ltd.
Jung, Doo Young,Park, Doo Han,Kim, Sung Han,Kim, Yong Hae
p. 1017 - 1022
(2007/10/03)

Stereoselective dimerization of benzylic amines derived from indoline
Treatment of benzylic amines derived from 2-(acyloxymethyl)-5-nitroindolines with sodium hexamethyldisilazide leads to dimeric products resulting from deprotonation in the benzylic position, oxidation of the resulting carbanion to radical by the nitroaren
Nowak, Ireneusz,George, Clifford
p. 895 - 900
(2007/10/03)

PYRIMIDINE-5-CARBOXAMIDE COMPOUNDS, PROCESS FOR PRODUCING THE SAME AND USE THEREOF
A compound of the formula wherein R1 is a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 nitrogen atom(s), which heterocycle is attached by a secondary nitrogen atom constituting the heterocycle; X is an oxygen atom, a nitrogen atom optionally substituted by a hydrocarbon group having 1 to 5 carbon atom(s) or a sulfur atom optionally oxidized with 1 or 2 oxygen, Y is a bond or a C1-5 alkylene group, R2 is (1) a hydrogen atom, (2) a hydroxy group, (3) a C1-5 alkoxy group, (4) a C1-5 alkylthio group, (5) a carbocycle having 3 to 15 carbon atoms or (6) a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 heteroatom(s), provided that when Y is a bond, R2 is a carbocycle having 3 to 15 carbon atoms or a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 heteroatom(s) and; one of R3 and R4 is a hydrogen atom or a group of the formula: -Z-R5 (Z is a bond or C1-10 alkylene group optionally having substituent(s) and R5 is (1) a hydrogen atom, (2) a hydroxy group, (3) a C1-5 alkoxy group, (4) a nitrile group, (5) a C1-5 alkoxy-carbonyl group, (6) a carboxyl group, (7) a carbamoyl group, (8) a (mono or di-C1-5 alkyl)carbamoyl group, (9) an amino group, (10) a (di or mono-C1-5 alkyl)amino group, (11) a (C1-5 alkoxy-carbonyl)amino group, (12) a C1-5 alkylthio group, (13) a carbocycle having 3 to 15 carbon atoms or (14) a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 heteroatom(s)); the other is a group of the formula: -Z-R5 (Z and R5 are as defined above); and R3 and R4 may form, together with the adjacent nitrogen atom, a heterocycle having a skeleton consisting of 3 to 15 atoms, which heterocycle is attached by a secondary nitrogen atom constituting the heterocycle, wherein the above-mentioned heterocycle and a carbocycle having 3 to 15 carbon atoms are each optionally substituted by substituent(s) selected from the group consisting of C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C7-16 aralkyl, C3-8 cycloalkyl, C3-8 cycloalkenyl, C6-14 aryl, C1-8 alkoxy, C1-3 alkylenedioxy, hydroxy, halogen atom, amino, (di or mono-C1-5 alkyl)amino, (C1-5 alkoxy-carbonyl)amino, (C1-5 acyl)amino, (C1-5 acyl) (C1-5 alkyl)amino, C1-5 alkylthio, nitrile, nitro, C1-5 alkoxy-carbonyl, carboxyl, C1-5 alkyl-carbonyloxy, oxo, thioxo, C1-6 acyl group, sulfamoyl and (di or mono-C1-5 alkyl)sulfamoyl, or a salt thereof or a prodrug thereof have a superior cGMP specific phosphodiesterase (PDE) inhibitory activity, and can be used as an agent for the prophylaxis or treatment of cardiovascular diseases such as angina pectoris, heart failure, cardiac infarction, hypertension, arteriosclerosis and the like, allergic diseases such as asthma, or disorders of male or female genital function and the like.
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(2008/06/13)

Heterocycle carboxamides as antiviral agents
The present invention provides a compound of formula I which is useful as antiviral agents, in particular, as agents against viruses of the herpes family.
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(2008/06/13)

Synthesis and application in enantioselective hydrogenation of new free and chromium complexed aminophosphine-phosphinite ligands
A straightforward synthesis of new free and Cr(CO)3 complexed AMPP ligands (4-7) is described starting from (S)-indoline-2-carboxylic acid. The ligands were applied successfully in the asymmetric hydrogenation of α-functionalized ketones i.e. a ketolactone 8, a ketoamide 9 and an aminoketone 10 leading to the corresponding optically active alcohols in 99, 97, and 99% ee respectively.
Pasquier, Corinne,Naili, Said,Pelinski, Lydie,Brocard, Jacques,Mortreux, Andre,Agbossou, Francine
p. 193 - 196
(2007/10/03)

Asymmetric Deprotonations: Lithiation of N-(tert-Butoxycarbonyl)indoline with sec-Butyllithium/ (-)-Sparteine
The asymmetric lithiation of N-Boc indoline (1) with s-BuLi/(-)-sparteine and subsequent substitution provides the 2-substituted N-Boc indolines 3 and 5-11 with excellent enantiomeric ratios and in variable yields. The asymmetric lithiation-substitution sequence with N-Boc-7-chloroindoline (12) provides products 13-19 with good enantiomeric ratios. Mechanistic investigation establishes that the enantioselectivities arise from an initial asymmetric deprotonation to provide the enantioenriched and configurationally stable organolithium intermediates (S)-28 and (S)-29, which react stereoselectively with electrophiles.
Bertini Gross, Kathleen M.,Jun, Young M.,Beak, Peter
p. 7679 - 7689
(2007/10/03)

Heterocyclic compounds having anti-diabetic activity and their use
Compounds of formula (I): STR1 [wherein: X represents an unsubstituted or substituted indolyl, indolinyl, azaindolyl, azaindolinyl, imidazopyridyl or imidazopyrimidinyl group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethyl group; R represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a nitro group, an aralkyl group or a unsubstituted or substituted amino group; and m is an integer of from 1 to 5] have hypoglycemic and anti-diabetic activities.
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(2008/06/13)

Tricyclic quinoxalinediones
Tricyclic quinoxalinediones of the formula: STR1 wherein X is alkyl, halogen, cyano, trifluoromethyl, nitro, hydroxy, amino, etc.; R 1 is H, etc.; R 2 is H, alkyl, cycloalkyl, alkenyl, alkynyl, cycloalkylalkyl, arylalkyl, substituted arylalkyl, aryl, or substituted aryl; W is H, CO 2 R 3, CO 2 Y, CONR 3 R 4, CONR 3 Y, CON(OR 3)R 4, COR 3, CN, tetrazolyl, or substituted alkyl; R 3 and R 4 independently are H, alkyl, cycloalkyl, alkenyl, alkynyl, etc.; Y is mono-substituted alkyl or di-substituted alkyl; and n is an integer 0 or 1, or a pharmaceutically acceptable salt thereof, which are useful as a selective antagonist of glutamate receptor for the treatment or prevention of various diseases in animals including human being, for example, minimizing damage of central nervous system induced by ischaemic or hypoxylic conditions, treatment and/or prevention of neurodegenerative disorders, and further analgesics, antidepressants, anxiolitics, and anti-schizophrenics.
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(2008/06/13)

AMINO-SUBSTITUTED PYRAZOLES HAVING CRF ANTAGONISTIC ACTIVITY
The invention relates to compounds of the formula I STR1 and to pharmaceutically acceptable salts thereof, wherein Z, A, Y, X 1, R. sub.1, R 2, and R 3 are as defined herein. The invention further relates to pharmaceutical compositions containing, and to
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(2008/06/13)

Diastereoselective addition of organolithiums to new chiral hydrazones. Enantioselective synthesis of (R)-coniine
The reactions of organolithiums with the new chiral hydrazones derived from (S)-indoline-2-carboxylic acid afforded chiral hydrazines with high diastereoselectivities (up to 99% de) and the present method was utilized for the preparation of high optically pure (R)-coniine (94% ee).
Kim, Yong Hae,Choi, Jun Young
p. 5543 - 5546
(2007/10/03)

Metal-catalyzed reaction of indoline diazoamides possessing a C-2 CH2X substituent: Site-selectivity, diastereoselectivity, and chemoselectivity
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Wee, Andrew G. H.,Slobodian
p. 2897 - 2900
(2007/10/03)

Tricyclic Quinoxalinediones: 5,6-Dihydro-1H-pyrroloquinoxaline-2,3-diones and 6,7-Dihydro-1H,5H-pyridoquinoxaline-2,3-diones as Potent Antagonists for the Glycine Binding Site of the NMDA Receptor
A series of tricyclic quinoxalinediones, 5,6-dihydro-1H-pyrroloquinoxaline-2,3-diones and 6,7-dihydro-1H,5H-pyridoquinoxaline-2,3-diones, were synthesized and was evaluated for their affinity for the glycine binding site of the NMDA receptor using a -5,7-dichlorokynurenic acid binding assay.The six-membered ring-fused tricyclic quinoxalinedione 18g (Ki = 9.9 nM) displayed high affinity for the glycine site.The anilide derivative 20g (Ki = 2.6 nM) was 4-fold more potent than 18g and as potent as L-689,560, one of the most potent glycineantagonists so far prepared.Although the carboxylic acid derivative of the corresponding five-membered ring-fused tricyclic quinoxalinedione 18e (Ki = 7.3 nM) had affinity comparable to that of 18g, the anilide derivative 20e largely decreased in the affinity in contrast to 20g.Enantiomers 23g, 24g, 25g, and 26g were prepared and tested.Only the S enantiomer 25g (Ki = 0.96 nM) retained the affinity among the anilide derivatives, whereas both enantiomers 23g (Ki = 2.3 nM) and 24g (Ki = 9.6 nM) were active among the carboxylic acid derivatives.The origin of the high affinity of carboxylic acid derivatives such as 18e and 18g would be a charge-charge interaction between the anionic carboxylate residues of the compounds and the cationic proton-donor site in the receptor.
Nagata, Ryu,Tanno, Norihiko,Kodo, Toru,Ae, Nobuyuki,Yamaguchi, Hiroshi,et al.
p. 3956 - 3968
(2007/10/02)

(Mercaptopropanoyl)indoline-2-carboxylic Acids and Related Compounds as Potent Angiotensin Converting Enzyme Inhibitors and Antihypertensive Agents
1-(3-Mercapto-2-methyl-1-oxopropyl)indoline-2-carboxylic acids (7b) and related compounds were synthesized in order to examine their ability to inhibit angiotensin converting enzyme (ACE) and to reduce the systolic blood pressure of spontaneously hypertensive rats (SHR).All four possible stereoisomers of the precursor 1-indoline-2-carboxylic acid (6b) were characterized with absolute stereochemical assigment.The removal of the benzoyl group of the precursor to give 7b was conveniently carried out by treatment with 2-methoxyethylamine.Three of the four stereoisomers of the benzoyl derivative 6 showed in vitro ACE inhibitory activity in the following order: 6b(S,S) > 6b(S,R) > 6b(R,S).The stereoisomer having the R,R configuration was essentialy inactive.The substitution at the C5 of the indoline nucleus with the Et or OMe group caused only marginal changes in the inhibitory activity.The mercaptan 7b(S,S) was the most active ACE inhibitor synthesized in this study, showing in vitro potency 3 times that of captopril.The augmentation of the potency may be due to the increased hydrophobicity of 7b (S,S) compared with captopril and suggests the presence of a hydrophobic pocket at the active site of ACE.When tested in spontaneously hypertensive rats, 7b(S,S) exhibited oral antihypertensive activity 27 times that of captopril.The corresponding benzoyl derivative 6b(S,S) was 24 times as potent as captopril.The thio lactone 10 obtained by cyclization of 7b(S,S) as a potential prodrug was less potent than the parent compound, 7b(S,S), in the ACE inhibitory and antihypertensive tests.
Kim, Dong H.,Guinosso, Charles J.,Buzby, George C.,Herbst, David R.,McCaully, Ronald J.,et al.
p. 394 - 403
(2007/10/02)

Stereoselective synthesis of a new perhydroindole derivative of chiral iminodiacid, a potent inhibitor of angiotensin converting enzyme
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Vincent,Remond,Portevin,et al.
p. 1677 - 1680
(2007/10/02)