N-(5-乙酰基-2-(苄氧基)苯基)甲磺酰胺 | 14347-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-(5-乙酰基-2-(苄氧基)苯基)甲磺酰胺
• 英文名称: 1-[4-Phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanone
• 英文别名: 4'-benzyloxy-3'-(methylsulfonylamino)acetophenone；3-mesylamino-4-benzyloxyacetophenone；1-(4-benzyloxy-3-methanesulphonamidophenyl)ethanone；N-(5-acetyl-2-benzyloxy-phenyl)-methanesulfonamide；5'-Acetyl-2'-benzyloxymethansulfonanilid；N-(5-acetyl-2-phenylmethoxyphenyl)methanesulfonamide
• CAS: 14347-08-1
• 化学式: C₁₆H₁₇NO₄S
• 分子量: 319.381
• InChiKey: LVZYLKCBQBQPSI-UHFFFAOYSA-N

物化性质

• 沸点：
  514.7±60.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(5-乙酰基-2-(苄氧基)苯基)甲磺酰胺 在 palladium on activated charcoal 盐酸 、 dimethyl sulfide borane 、 氢气 、 溴 、 sodium ethanolate 作用下， 以 氯仿 、 丁酮 为溶剂， 反应 12.0h， 生成 N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulfonamide;hydrochloride
  参考文献：
  名称：

  Synthesis and structure-activity relationships among .alpha.-adrenergic receptor agonists of the phenylethanolamine type

  摘要：

  Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for alpha-adrenergic stimulant activity. In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, chlohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups. The other series is meta hydroxylated with the para position substituted by the same groups. The influence of these groups upon the alpha-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine, norepinephrine, and norphenylephrine. It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental. The most active compound, alpha-(aminomethyl)(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundredth the affinity and the same intrinsic activity as norepinephrine.

  DOI：

  10.1021/jm00181a008
• 作为产物：
  描述：

  溴甲苯 在 吡啶 、 platinum(IV) oxide 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 20.0~25.0 ℃ 、103.0 kPa 条件下， 反应 28.0h， 生成 N-(5-乙酰基-2-(苄氧基)苯基)甲磺酰胺
  参考文献：
  名称：

  Development of an Enabling Route to PF-00610355: A Novel Inhaled β₂-Adrenoreceptor Agonist

  摘要：

  The initial route used to prepare PF-00610355 (8) for early clinical development is described. Through careful choice of solvent, an efficient, telescoped route to carboxylic acid 23 was developed, affording this late-stage intermediate in 80% yield over 4 steps. Deprotection of 23 to give sodium salt 24a and coupling with amine 6 center dot HCl afforded the desired API. Effective synthetic routes to two of the starting materials, chiral bromide 1 and amine 6, are also described.

  DOI：

  10.1021/op2001904

文献信息

• Fibrinogen receptor antagonists and their use
  申请人：Piramal Life Sciences Limited

  公开号：US07759387B2

  公开（公告）日：2010-07-20

  This invention relates to novel fused bicyclic compounds of the general formula (I): wherein the symbols are defined herein, to pharmaceutical compositions containing the compounds, processes for preparing the compounds, and to methods of using the compounds, alone or in combination with other therapeutic agents. The compounds are antagonists of the platelet glycoprotein IIb/IIIa fibrinogen receptor complex, and are therefore useful for the inhibition of platelet aggregation, and for the treatment of thrombotic diseases and other diseases.

  这项发明涉及一般式(I)的新型融合双环化合物： 其中符号在此定义，包括含有这些化合物的药物组合物、制备这些化合物的方法，以及使用这些化合物的方法，单独或与其他治疗剂联合使用。这些化合物是血小板糖蛋白IIb/IIIa纤维蛋白原受体复合物的拮抗剂，因此对于抑制血小板聚集以及治疗血栓性疾病和其他疾病是有用的。
• Catecholamine surrogates useful as .beta..sub.3 agonists
  申请人：Bristol-Myers Squibb Company

  公开号：US05776983A1

  公开（公告）日：1998-07-07

  Compounds of the formula ##STR1## or pharmaceutically acceptable salts thereof wherein: A is a bond, --(CH.sub.2).sub.n -- or --CH(B)--, where n is an integer of 1 to 3 and B is --CN, --CON(R.sup.9)R.sup.9' or --CO.sub.2 R.sup.7 ; R.sup.1 is lower alkyl, aryl or arylalkyl; R.sup.2 is hydrogen, hydroxy, alkoxy, --CH.sub.2 OH, cyano, --C(O)OR.sup.7, --CO.sub.2 H, --CONH.sub.2, tetrazole, --CH.sub.2 NH.sub.2 or halogen; ##STR2## R.sup.3 is hydrogen, alkyl, heterocycle or R.sup.4 is hydrogen, alkyl or B; R.sup.5, R.sup.5', R.sup.8, R.sup.8' or R.sup.8" are independently hydrogen, alkoxy, lower alkyl, halogen, --OH, --CN, --(CH.sub.2).sub.n NR.sup.6 COR.sup.7, --CON(R.sup.6)R.sup.6', --CON(R.sup.6)OR.sup.6', --CO.sub.2 R.sup.6, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, --N(R.sup.6)SO.sub.2 R.sup.1, --N(R.sup.6)R.sup.6', --NR.sup.6 COR.sup.7, --OCH.sub.2 CON(R.sup.6)R.sup.6', --OCH.sub.2 CO.sub.2 R.sup.7 or aryl; or R.sup.5 and R.sup.5' or R.sup.8 and R.sup.8' may together with the carbon atoms to which they are attached form an aryl or heterocycle; R.sup.6 and R.sup.6' are independently hydrogen or lower alkyl; and R.sup.7 is lower alkyl; R.sup.9 is hydrogen, lower alkyl, alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl; or R.sup.9 and R.sup.9' may together with the nitrogen atom to which they are attached form a heterocycle; with the proviso that when A is a bond or --(CH.sub.2).sub.n and R.sup.3 is hydrogen or unsubstituted alkyl, then R.sup.4 is B or substituted alkyl. These compounds are beta.sub.3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity and gastrointestinal diseases.

  公式为##STR1##的化合物或其药学上可接受的盐，其中：A是键，--(CH.sub.2).sub.n --或--CH(B)--，其中n是1到3的整数，B是--CN，--CON(R.sup.9)R.sup.9'或--CO.sub.2 R.sup.7；R.sup.1是较低的烷基，芳基或芳基烷基；R.sup.2是氢，羟基，烷氧基，--CH.sub.2 OH，氰基，--C(O)OR.sup.7，--CO.sub.2 H，--CONH.sub.2，四唑基，--CH.sub.2 NH.sub.2或卤素；##STR2## R.sup.3是氢，烷基，杂环或R.sup.4是氢，烷基或B；R.sup.5，R.sup.5'，R.sup.8，R.sup.8'或R.sup.8"独立地是氢，烷氧基，较低烷基，卤素，--OH，--CN，--(CH.sub.2).sub.n NR.sup.6 COR.sup.7，--CON(R.sup.6)R.sup.6'，--CON(R.sup.6)OR.sup.6'，--CO.sub.2 R.sup.6，--SR.sup.7，--SOR.sup.7，--SO.sub.2 R.sup.7，--N(R.sup.6)SO.sub.2 R.sup.1，--N(R.sup.6)R.sup.6'，--NR.sup.6 COR.sup.7，--OCH.sub.2 CON(R.sup.6)R.sup.6'，--OCH.sub.2 CO.sub.2 R.sup.7或芳基；或R.sup.5和R.sup.5'或R.sup.8和R.sup.8'可以与它们连接的碳原子一起形成芳基或杂环；R.sup.6和R.sup.6'独立地是氢或较低烷基；R.sup.7是较低烷基；R.sup.9是氢，较低烷基，烷基，环烷基，芳基烷基，芳基，杂芳基；或R.sup.9和R.sup.9'可以与它们连接的氮原子一起形成杂环；但是当A是键或--(CH.sub.2).sub.n且R.sup.3是氢或未取代烷基时，R.sup.4是B或取代烷基。这些化合物是β.sub.3肾上腺素受体激动剂，因此在糖尿病、肥胖症和胃肠疾病的治疗中很有用。
• 7[(2-Hydroxyamino-2-disubstituted
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04143166A1

  公开（公告）日：1979-03-06

  The new 7-(.alpha.,.alpha.-disubstituted-acetamido)-3-substituted-3-cephem-4-carbo xylic acid of the present invention is represented by the following formula: ##STR1## wherein R.sup.1 is hydrogen, halogen, hydroxy, nitro, lower alkoxy or acylamino, R.sup.2 is hydrogen or acyl and R.sup.3 is lower alkanoyloxy, carbamoyloxy which may have lower alkyl, aryl or protective group for amino, or a heterocyclicthio which may have lower alkyl, aryl or protective group for amino, or a hetero- which may have lower alkyl.

  本发明的新7-(.alpha.,.alpha.-二取代-乙酰胺基)-3-取代-3-头孢-4-羧酸的化学式如下所示：##STR1##其中R.sup.1为氢、卤素、羟基、硝基、低烷氧基或酰氨基，R.sup.2为氢或酰基，R.sup.3为低烷酰氧基、氨基甲酰氧基，可能具有低烷基、芳基或氨基的保护基，或可能具有低烷基、芳基或氨基的杂环硫基，或可能具有低烷基的杂环基。
• PROCESS FOR THE PREPARATION OF TRICYCLIC AMINO ALCOHOL DERIVATIVES
  申请人：Asahi Kasei Kabushiki Kaisha

  公开号：EP1195371A1

  公开（公告）日：2002-04-10

  A process for the preparation of tricyclic amino alcohol derivatives of formula (1) or salts thereof which are useful in the treatment and prevention of diabetes, obesity, hyperlipidemia and so on; and intermediates useful for the process: wherein R1 is lower alkyl group or benzyl; *1 represents an asymmetric carbon atom; R2 is hydrogen, halogen, or hydroxyl; and A is one of the following groups: (wherein X is NH, O or S; R6 is hydrogen, hydroxyl, amino, or acetylamino; and *2 represents an asymmetric carbon atom when R6 is not hydrogen)

  一种用于制备式（1）的三环氨基醇衍生物或其盐的方法，该方法有助于治疗和预防糖尿病、肥胖、高脂血症等疾病；以及用于该方法的中间体：其中R1是较低的烷基或苄基；*1代表一个不对称碳原子；R2是氢、卤素或羟基；A是以下组之一：（其中X是NH、O或S；R6是氢、羟基、氨基或乙酰氨基；当R6不是氢时，*2代表一个不对称碳原子）
• Adrenergic agents. 4. Substituted phenoxypropanolamine derivatives as potential .beta.-adrenergic agonists
  作者：Carl Kaiser、Timothy Jen、Eleanor Garvey、Wayne D. Bowen、Donald F. Colella、Joe R. Wardell

  DOI：10.1021/jm00215a014

  日期：1977.5

  coupled with NMR spectral data, it appears that the previous suggestion that aryloxypropanolamines interact with beta-adrenocreceptors as a consequence of their ability to assume an orientation in which the benzene ring the ethanolamine moieties can be superimposed on those of corresponding adrenergic phenylethanolamines is invalid. An alternative "bicyclic" rigid conformation involving two intramolecular

  一系列的1-（取代的苯氧基）-3-（叔丁基氨基）-2-丙醇，其环取代基是3,4-二羟基（6f），3-和4-羟基（分别为6g和6h），制备3-羟基-4-甲基磺酰胺基（6i），其3,4-转位异构体（6j）和4-甲基磺酰基甲基（6k），并检查其β-肾上腺素能激动剂和/或拮抗剂的性能。这些化合物中的两个6f和6j在体外测试中是有效的β肾上腺素受体激动剂，可测量该化合物放松豚鼠气管平滑肌并提高豚鼠右心房收缩率的能力。几种化合物具有剂量依赖性作用。尽管它们在低浓度下产生有效的β-肾上腺素能激动剂活性，但6g，6h和6j却在较高浓度下拮抗了标准β-肾上腺素能受体激动剂的作用。甲基磺酰基甲基衍生物6k产生β-肾上腺素阻断作用，如异丙肾上腺素诱导的离体兔心脏制剂收缩率增加的减弱所证明。根据这些药理学结果，再结合NMR光谱数据，似乎先前的建议是芳氧基丙醇胺与β-肾上腺素受体相互作用，这是由于它们具有以下能力：