Benzocyclobutene Derivatives. Oximes with Muscle Relaxant Characteristics<sup>1</sup>

Ja, Skorcz; Jt, Suh; Ci, Judd

doi:10.1021/jm00323a004

Cited by 22 publications

(5 citation statements)

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“…[48] Similarly, isothiazolo[4,3-b]pyridine 2,2-dioxide (51) can be obtained from 2-chloro-3-(sulfonylamino)pyridine (50). [50,51] An aryne-mediated intramolecular substitution in 2-chloro-N-methyl-N-methanesulfonylaniline (52) [52,53] and (2-bromophenyl)methanesulfonamide (57) [54] results in The simplest benzosultam (59) can also be obtained upon treatment of sodium (2-aminophenyl)methanesulfonate (55) with POCl 3 (36% yield) [55] or by cyclization of (2-chlorophenyl)methanesulfonamide (56) in the presence of K 2 CO 3 and copper bronze (62% yield), [55] as shown in Scheme 14.…”

Section: Synthesis Of Benzosultamsmentioning

confidence: 99%

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Aza-ortho-xylylenes in Organic Synthesis

Wojciechowski

2001

Eur. J. Org. Chem.

129

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Section: Synthesis Of Benzosultamsmentioning

confidence: 99%

“…Further functionalization of the obtained N-alkyl-benzosultams by alkylation (Scheme 11), [51,56,57] nitroarylation, [49,51,56,58] and Knoevenagel condensation with aldehydes [56,59] provides the 3-substituted benzosultams.…”

Section: Synthesis Of Benzosultamsmentioning

confidence: 99%

Aza-ortho-xylylenes in Organic Synthesis

Wojciechowski

2001

Eur. J. Org. Chem.

129

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“…As an alternative to the condensation of an aldehyde with cyanoacetic acid, the appropriately substituted benzyl halide was used to alkylate methyl cyanoacetate in three cases. The resulting a-cyanocarboxylic ester was then saponified (NaOH) and the acid decarboxylated by heating in MJV-dimethylformamide to give the desired 3-substituted benzenepropanenitrile 2k, 1, and m. 56 2-(Benzyloxy)benzenepropanenitrile (2e), 4-iodobenzenepropanenitrile (2p), and 2,3,5-trichlorobenzenepropanenitrile (2v) are the only substituted propanenitriles that have not been reported. The next step of the synthetic sequence was the preparation of the 2-formylpropanenitriles 3.…”

Section: Introductionmentioning

confidence: 99%

Structure-based design of inhibitors of purine nucleoside phosphorylase. 1. 9-(Arylmethyl) derivatives of 9-deazaguanine

Montgomery¹,

Niwas²,

Rose³

et al. 1993

J. Med. Chem.

130

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Purine nucleoside phosphorylase (PNP, EC 2.4.2.1) is a salvage enzyme important to the T-cell-mediated part of the immune system and as such is an important therapeutic target. This paper describes the design, synthesis, and enzymatic evaluation of potent, competitive inhibitors of PNP. Potential inhibitors were designed using the three-dimensional structure of the enzyme in an iterative process that involved interactive computer graphics to model the native enzyme and complexes of it with the inhibitors, Monte Carlo-based conformational searching, and energy minimization. Studies of the enzyme/inhibitor complexes were used to determine priorities of the synthetic efforts. The resulting compounds were then evaluated by determination of their IC50 values and by X-ray diffraction analysis using difference Fourier maps. In this manner, we have developed a series of 9-(arylmethyl)-9-deazapurines (2-amino-7-(arylmethyl)-4H-pyrrolo[3,2-d]-pyrimidin-4-ones) that are potent, membrane-permeable inhibitors of the enzyme. The IC50 values of these compounds range from 17 to 270 nM (in 1 mM phosphate), with 9-(3,4-dichlorobenzyl)-9-deazaguanine being the most potent inhibitor. X-ray analysis explained the role of the aryl groups and revealed the rearrangement of hydrogen bonds in the binding of the 9-deazaguanines in the active site of PNP relative to the binding of the 8-aminoguanines that results in more potent inhibition of the enzyme.

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“…A racemic total synthesis of trichodermamide B based on this methodology was reported [9]. opening reactions by oximes to form O-alkylated products were reported by several groups, though most afforeded low yields [30][31][32][33]. Intramolecular O-alkylation of oximes for the formation of the oxazine ring was first introduced by Woodward in 1979 (Scheme 8, entry 1) [34].…”

Section: Lewis Acid-promoted 12-oxaza Cope Rearrangementmentioning

confidence: 99%