5600-63-5

Usage

InChI:InChI=1/C10H10ClNO3/c11-10(13)3-1-2-8-4-6-9(7-5-8)12(14)15/h4-7H,1-3H2

Upstream product

• 79-37-8 oxalyl dichloride 
• 5600-62-4 4-(4-nitrophenyl)butanoic acid 

Downstream Products

• 95461-37-3 N,N'''-Di<γ-(p-nitrophenyl)butyryl>-N',N''-dispirotripiperazinium dichloride 
• 143665-55-8 N-(3,4-Dimethoxy-benzyl)-N-methyl-4-(4-nitro-phenyl)-butyramide 
• 169898-36-6 methyl 12α-hydroxy-3α-<4-(4-nitrophenyl)butanoyloxy>-5β-cholan-24-oate 
• 169898-38-8 methyl 3α-<(4-nitrophenyl)acetoxy>-12α-<4-(4-nitrophenyl)butanoyloxy>-5β-cholan-24-oate 
• 61445-60-1 4-(4-nitro-phenyl)-butyric acid amide 
• 138909-46-3 (S)-1-<4-(4-nitrophenyl)butyryl>pyrrolidine-2-carboxylic acid 
• 493005-73-5 (S)-4-Methylsulfanyl-2-{4-[4-(4-nitro-phenyl)-butyrylamino]-benzoylamino}-butyric acid methyl ester 
• 269402-54-2 N/[3-(dimethylamino)propyl]-4-{4-[bis(2-chloroethyl)amino]phenyl}-butyramide 
• 218629-17-5 dimethyl 2,3-dihydro-5-<3-(4-aminophenyl)propyl>-1H-pyrrolizine-6,7-dicarboxylate 
• 218629-16-4 dimethyl 2,3-dihydro-5-<3-(4-nitrophenyl)propyl>-1H-pyrrolizine-6,7-dicarboxylate 
• 427897-34-5 1-(4-Fluorophenyl)-4-(4-nitrophenyl)-butan-1-one 
• 93130-63-3 4-(4-Guanidino-phenyl)-butyric acid phenyl ester; compound with methanesulfonic acid 
• 93131-00-1 4-(4-Amino-phenyl)-butyric acid phenyl ester; hydrochloride 
• 143665-56-9 4-(4-Amino-phenyl)-N-(3,4-dimethoxy-benzyl)-N-methyl-butyramide 

Relevant academic research and scientific papers

Ruthenium(II)-Catalyzed Enantioselective ?-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-Ones

We report the Ru-Catalyzed enantioselective annulation of 1,4,2-Dioxazol-5-Ones to furnish ?-Lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C-H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-Withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- A nd enantioselectivities; the competing Curtius-Type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C-H bonds was also achieved with remarkable tolerance to the Ca?C and Ca‰iC bonds.

Ruthenium(II)-Catalyzed Enantioselective γ-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-ones

We report the Ru-catalyzed enantioselective annulation of 1,4,2-dioxazol-5-ones to furnish γ-lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C - H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- and enantioselectivities; the competing Curtius-type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C - H bonds was also achieved with remarkable tolerance to the C=C and C=C bonds.

Non- C2-Symmetric Chiral-at-Ruthenium Catalyst for Highly Efficient Enantioselective Intramolecular C(sp3)-H Amidation

A new class of chiral ruthenium catalysts is introduced in which ruthenium is cyclometalated by two 7-methyl-1,7-phenanthrolinium heterocycles, resulting in chelating pyridylidene remote N-heterocyclic carbene ligands (rNHCs). The overall chirality results from a stereogenic metal center featuring either a or Δabsolute configuration. This work features the importance of the relative metal-centered stereochemistry. Only the non-C2-symmetric chiral-at-ruthenium complexes display unprecedented catalytic activity for the intramolecular C(sp3)-H amidation of 1,4,2-dioxazol-5-ones to provide chiral -lactams with up to 99:1 er and catalyst loadings down to 0.005 mol % (up to 11 ?200 TON), while the C2-symmetric diastereomer favors an undesired Curtius-type rearrangement. DFT calculations elucidate the origins of the superior C-H amidation reactivity displayed by the non-C2-symmetric catalysts compared to related C2-symmetric counterparts.

Synthesis of a novel 'smart' bifunctional chelating agent 1-(2-[β,d-galactopyranosyloxy]ethyl)-7-(1-carboxy-3-[4-aminophenyl]propyl)-4,10-bis(carboxymethyl)-1,4,7,10-tetraazacyclododecane (Gal-PA-DO3A-NH2) and its Gd(III) complex

A new synthetic pathway to 1-(2-[β,d-galactopyranosyloxy]ethyl)-7-(1-carboxy-3-[4-aminophenyl]propyl)-4,10-bis(carboxymethyl)-1,4,7,10-tetraazacyclododecane (Gal-PA-DO3A-NH2) and 1-(2-[β,d-galactopyranosyloxy]ethyl)-4,7,10-tris(carboxymethyl)-1, 4,7,10-tetraazacyclododecane (Gal-DO3A) chelating agents was developed involving full hydroxyl- and carboxyl-group protection in precursors to product. Two sequences of cyclen-N-functionalisation were subsequently investigated, one successfully, towards synthesis of the novel 'smart' bifunctional Gal-PA-DO3A-NH2 chelate. The longitudinal proton relaxivities of the neutral [Gd-(Gal-PA-DO3A-NH2)] and [Gd-(Gal-DO3A)] complexes were increased by 28% and 37% in the presence of β-galactosidase, respectively.

BENZTROPINE COMPOUNDS AND USES THEREOF

Disclosed are benztropine analogs having the formula (I) in which Ar is a C6-C20 monocyclic aryl group or a C10-C20 bicyclic aryl group or a heteroaryl, heterocyclic, or arylheterocyclic group having 2 to 12 carbon atoms and one or more heteroatoms selected from the group consisting of N, O, S, P, and any combination thereof; m = 1 to 5; n = 1 to 3; and R1 to R4 are as described in the specification; or a pharmaceutically acceptable salt or solvate thereof; pharmaceutical compositions and use thereof, e.g., in treating mental disorders.

Synthesis and pharmacokinetic profile of a quaternary ammonium derivative of chlorambucil, a potential anticancer drug for the chemotherapy of chondrosarcoma

As a part of our targeting program based on the affinity of the quaternary ammonium moiety for cartilage, our objective was to develop more selective anticancer drugs towards chondrosarcoma that would concentrate in this malignant cartilaginous tissue and so improve the therapeutic index through a reduction of side effects. For this purpose we have synthesized and labeled with 14C a quaternary ammonium (QA) derivative of chlorambucil. Biological studies performed in rats showed that [14C]-CQA and [ 14C]-chlorambucil exhibited different pharmacokinetic profiles. The blood elimination of [14C]-CQA was faster than that of parent compound. [14C]-CQA was principally excreted by the fecal way. However, until 15 min after administration, levels of radioactivity were measured in cartilaginous tissues of rats given [14C]-CQA which was not the case for the rats which had received [14C]-chlorambucil. Although rates of radioactivity were quantified only during 15 min, these results prove that the functionalization of chlorambucil by a quaternary ammonium group allows the molecule to be carried selectively to cartilaginous tissues.

Non-thiol farnesyltransferase inhibitors: Evaluation of different AA(X)-peptidomimetic substructures in combination with arylic cysteine replacements

In the course of our studies on non-thiol farnesyltransferase inhibitors based on the 2,5-diaminobenzophenone AAX-peptidomimetic substructure, we have developed the (4-nitrophenyl)butyryl (R1), the (2-naphthyl)acryloyl (R2), the 4-nitrocinnamoyl (R3), and the 5-(4-nitrophenyl)furylacryloyl (R4) groups as useful cysteine replacements. In this study, we combined these four groups with other AA(X)-peptidomimetic substructures (5-10: R = H) reported in the literature. The 5-(4-nitrophenyl)furylacryloyl moiety (R4) turned out to be the most useful non-thiol cysteine replacement yielding in all cases the most active inhibitors. By combination of this 5-(4-nitrophenyl)furylacryloyl moiety (R4) with the structurally simple AAX-peptidomimetics 4-aminobenzophenone (5) and 4-aminodiphenylsulfone (6) potent, readily accessible non-thiol farnesyltransferase inhibitors were obtained (IC50 = 12 nM and 10 nM).

Non-thiol farnesyltransferase inhibitors: Structure-activity relationships of aralkylsubsituted benzophenones

We describe a novel class of benzophenone-based farnesyltransferase inhibitors exploiting a novel aryl binding region in the farnesyltransferase's active site. The present study was mainly focussed on structural modifications of the trimethylene spacer of the 4-phenyl butyroyl residue of our lead structure (IC50 = 530 nM). These modifications turned out to have little effect on activity as had the replacement of the terminal aryl by cyclohexyl (IC50 = 440 nM vs. IC50 = 530 nM).

Synthesis and pharmacological characterization of novel 6-fluorochroman derivatives as potential 5-HT(1A) receptor antagonists

A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT(1A) receptor. N-2-[[(6-Fluorochroman-8- yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252- 1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT(1A) receptor, some of which were selective with respect to α1-adrenergic and D2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolinstimulated adenylate cyclase assays in CHO cells expressing the human 5-HT(1A) receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screens and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3- benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT- induced behavioral and electrophysiological responses in rats.

Catechol based inhibitors of 15-lipoxygenase

A potent 15-lipoxygenase (15-LO) inhibitor, compound 6, was identified by mass screening the Parke-Davis compound portfolio. The active moiety of compound 6 was determined to be the catechol functionality. Additional analogs were prepared and analyzed for inhibitory activity against 5-, 12-, and 15-lipoxygenase.