93407-96-6

Usage

Molecular weight

315.4

Appearance

White crystalline solid

Solubility

Soluble in common organic solvents such as ethanol, methanol, and acetonitrile

Purity

>=98% (HPLC)

Melting point

85-88°C

Derivation

Synthesized from ethylamine and 4-methylbenzenesulfonyl chloride

Use

Commonly used as a protecting group for the amino group in organic synthesis, especially in peptide synthesis

Selective removal

The Z-group can be selectively removed under mild acidic or basic conditions without affecting the rest of the molecule.

Upstream product

• 77987-49-6 benzyl 2-hydroxyethylcarbamate 
• 98-59-9 p-toluenesulfonyl chloride 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 25711-25-5 benzyl aziridine-1-carboxylate 
• 263011-15-0 {2-[(2-dimethylamino-ethyl)-methyl-amino]-ethyl}-carbamic acid benzyl ester 
• 343248-63-5 (2S)-N-(N'-(benzyloxycarbonyl)-2'-aminoethyl)-proline methyl ester 
• 439093-09-1 {2-[(3-dimethylamino-propyl)-methyl-amino]-ethyl}-carbamic acid benzyl ester 
• 696617-49-9 N-(4-phenylbutyl)-N-(benzyloxycarbonyl)ethane-1,2-diamine 
• 147688-25-3 N-Benzyl-N'-benzyloxycarbonyl-ethylenediamine 
• 147688-15-1 13-Benzyloxycarbonylaminoethylen-1,4,7,10-tetraoxa-13-azacyclopentadecane 
• 147688-17-3 16-Benzyloxycarbonylaminoethylene-1,4,7,10,13-pentaoxa-16-azacyclooctadecane 
• 147688-19-5 7,16-Bis(benzyloxycarbonylaminoethylene)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane 
• 147688-26-4 3,9-Dibenzyl-1,11-bis(benzyloxycarbonylamino)-6-oxa-3,9-diazaundecane-4,8-dione 
• 1226998-66-8 BrH*C₁₀H₁₅NS 
• 133118-02-2 4'-(2-(N-benzyloxycarbonylamino)ethoxy)-acetophenone 
• 299422-78-9 C₁₇H₁₉ClNO₄P 

Relevant academic research and scientific papers

Preparation method of N-(2-aminoethyl) morpholine

The invention provides a preparation method of N-(2-aminoethyl) morpholine, which comprises the following steps: S1, adding ethanolamine into dichloromethane to fully dissolve, dropwise adding benzyl chloroformate into the solution, and reacting under alkaline conditions to generate an intermediate 1; S2, adding the intermediate 1 into dichloromethane, fully dissolving, dropwise adding 4toluenesulfonyl chloride, and reacting under an alkaline condition to generate an intermediate 2; S3, adding the intermediate 2 into acetonitrile to be fully dissolved, adding morpholine into the acetonitrile to generate an intermediate 3, wherein the structural formula of the intermediate 3 is shown as the following formula (3); and S4, adding the intermediate 3 into methanol, fully dissolving, and carrying out a catalytic hydrogenation reaction under the action of a catalyst to generate N-(2-aminoethyl)morpholine. According to the N-(2-aminoethyl)morpholine preparation method provided by the embodiment of the invention, the raw materials used in the reaction are cheap and easily available, the toxicity is low, the operation is simple and convenient, and the method has less three wastes and is more environment-friendly.

Identification of Highly Selective Lipoprotein-Associated Phospholipase A2 (Lp-PLA2) Inhibitors by a Covalent Fragment-Based Approach

Covalent ligands are of great interest as therapeutic drugs or biochemical tools. Here, we reported the discovery of highly selective and irreversible inhibitors of lipoprotein-associated phospholipase A2 (Lp-PLA2) using a covalent fragment-based approach. The crystal structure of Lp-PLA2 in complex with a covalent fragment not only reveals the covalent reaction mechanism but also provides a good starting point to design compound 8, which has a more than 130,000-fold and 3900-fold increase in potency and selectivity, respectively, compared to those of the covalent fragment. Furthermore, fluorescent probes with high selectivity and sensitivity are developed to characterize Lp-PLA2 and its enzymatic activity in vitro or even in living cells in a way more convenient than immunoblotting tests or immunofluorescence imaging. Overall, we provide a paradigm for application of the covalent fragment-based strategy in covalent ligand discovery and the advantage of enol-cyclocarbamate as a new warhead in designing covalent inhibitors of serine hydrolases.

Oxazolidinone compound as well as preparation method, application and pharmaceutical composition thereof

The invention relates to an oxazolidinone compound used as an Lp-PLA2 covalent inhibitor and a pharmaceutical composition of the oxazolidinone compound, the structure of the oxazolidinone compound isshown as a general formula I, and R1, R2 and R3 are defined as the specification and claims. The compound shown in the general formula I or the stereoisomer or the pharmaceutically acceptable salt thereof can be used as the Lp-PLA2 covalent inhibitor to prevent and/or treat and/or improve diseases related to Lp-PLA2 enzyme activity. Meanwhile, the stereoisomer or the pharmaceutically acceptable salt of the compound shown in the general formula I can be used as an Lp-PLA2 specific molecular probe.

Design, Synthesis, and Structure-Activity Relationships of Novel Tetrahydroisoquinolino Benzodiazepine Dimer Antitumor Agents and Their Application in Antibody-Drug Conjugates

A series of tetrahydroisoquinoline-based benzodiazepine dimers were synthesized and tested for in vitro cytotoxicity against a panel of cancer cell lines. Structure-activity relationship investigation of various spacers guided by molecular modeling studie

CONJUGATED CHEMICAL INDUCERS OF DEGRADATION AND METHODS OF USE

The subject matter described herein is directed to antibody-CIDE conjugates (Ab-CIDEs), to pharmaceutical compositions containing them, and to their use in treating diseases and conditions where targeted protein degradation is beneficial.

Modular One-Step Three-Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy

Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.

CONJUGATES COMPRISING SELF-IMMOLATIVE GROUPS AND METHODS RELATED THERETO

In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and an active agent. The antibody-drug conjugate may comprise a self- immolative group. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

CONJUGATES COMPRISING PEPTIDE GROUPS AND METHODS RELATED THERETO

In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and at least two active agents. In preferred embodiments, the linker comprises a peptide sequence of a plurality of amino acids, and at least two of the active agents are covalently coupled to side chains of the amino acids. The antibody-drug conjugate may comprise a self-immolative group, preferably two-self-immolative groups. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

Removal of the phosphate group in mechanism-based inhibitors of inositol monophosphatase leads to unusual inhibitory activity.

Inositol monophosphatase is widely held to be the therapeutic target for inhibition by lithium ion in the treatment of bipolar disorder. In a continued effort to improve the bioavailability of alternative inhibitors, we have designed and tested two new se

Nonpeptide bradykinin B2 receptor antagonists: Conversion of rodent-selective bradyzide analogues into potent, orally-active human bradykinin B2 receptor antagonists

The 1-(2-nitrophenyl)thiosemicarbazide (TSC) derivative, (S)-l-[4-(4-benzhydrylthiosemicarbazido)-3-nitrobenzenesulfonyl] pyrrolidine-2-carboxylic acid {2-[(2-dimethylaminoethyl)methylamino]ethyl} amide (bradyzide; (S)-4), was recently disclosed as a novel, potent, orally active nonpeptide bradykinin (BK) B2 receptor antagonist. The compound inhibited the specific binding of [3H]BK to NG108-15 cell membrane preparations (rodent neuroblastoma-glioma) expressing B2 receptors with a Ki of 0.5 ± 0.2 nM. Compound (S)-4 also demonstrated oral efficacy against Freund's complete adjuvant (FCA)-induced mechanical hyperalgesia in rats with an ED50 value of 0.84 μmol/kg. After we optimized the terminal binding determinants projecting from the TSC framework, we found that it was possible to replace the potentially toxicophoric nitro and divalent sulfur moieties with only a 15-fold loss in binding affinity ((S)-14a). However, bradyzide and its congeners were found to have much lower affinities for cloned human B2 receptors, expressed in Cos-7 cells. The hitherto synthesized TSC series was screened against the human B2 receptor, and the dibenzosuberane (DBS) pharmacophore emerged as the key structural requirement for potency. Incorporation of this group resulted in a series of derivatives ((S)-14d,e and 19b-d) with Ki ranges of 10.7-176 nM in NG108-15 cells (expressing the rodent B2 receptor) and 0.79-253 nM in Cos-7 cells (expressing the human B2 receptor). There was no evidence of agonist activity with any of the nonpeptides in any of the cell lines tested. In vivo, oral administration of compound 19c reversed FCA-induced and turpentine-induced mechanical hyperalgesia in rodents with ED50 values of 0.027 and 0.32 μmol/kg, respectively. The selectivity profiles of compounds (S)-14f and (S)-14g were also assessed to determine the conformational and/or steric preferences of the double-ring arrangement. The affinity of (S)-14g for the human B2 receptor suggested that it may be a hydrophobic interaction with the ethane bridge of the DBS moiety that accounts for the increased potency of compounds (S)-14d,e and 19b,c at this receptor, by favoring a binding mode inaccessible to the unsubstituted diphenylmethyl derivative, (S)-4.