(S)-1-(2-naphthyl-sulfonyl)pyrrolidine-2-carbonyl chloride | 91872-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-(2-naphthyl-sulfonyl)pyrrolidine-2-carbonyl chloride
• 英文别名: N-(2-naphthylsulfonyl)-(S)-prolyl chloride；(2S)-1-(2-naphthylsulfonyl)pyrrolidin-2-carbonyl chloride；(S)-N-(2-naphthalenesulfonyl)prolyl chloride；(S)-1-(2-naphthylsulfonyl)pyrrolidine-2-carboxylic acid chloride；(S)-1-(2-naphthylsulfonyl)pyrrolidine-2-carbonyl chloride；(S)-1-(2-naphthylsulfonyl)pyrrolidin-2-carbonyl chloride；(2S)-1-naphthalen-2-ylsulfonylpyrrolidine-2-carbonyl chloride
• CAS: 91872-31-0
• 化学式: C₁₅H₁₄ClNO₃S
• 分子量: 323.8
• InChiKey: JHVKQEXNQYGGOH-AWEZNQCLSA-N

物化性质

• 沸点：
  495.4±55.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-naphthyl-sulfonyl)pyrrolidine-2-carbonyl chloride 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-Allyl-9-[(S)-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-1,9-dihydro-β-carboline-2-carboxylic acid phenyl ester
  参考文献：
  名称：

  A Novel Synthesis of Chiral 1-Allyl-1,2,3,4-tetrahydro-β-carboline Employing Allyltributyltin and Chiral Acyl Chlorides

  摘要：

  β-咔啉在其9-位被手性酰氯酰化，然后与烯丙基三丁基锡和2,2,2-三氯乙基氯甲酸酯反应以非对映选择性方式提供1-烯丙基-1,2-二氢咔啉衍生物。 N-9位上的手性酰基很容易被碱水溶液消除，定量地得到羧酸，而C-1位上没有外消旋化。形成的1-烯丙基-1,2-二氢-β-咔啉转化为1-烯丙基-1,2,3,4-四氢-β-咔啉。

  DOI：

  10.1055/s-1999-2952
• 作为产物：
  描述：

  N-(2-naphthylsulfonyl)-(S)-proline 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 反应 6.0h， 以96%的产率得到(S)-1-(2-naphthyl-sulfonyl)pyrrolidine-2-carbonyl chloride
  参考文献：
  名称：

  N-甲苯磺酰基-（S）-脯氨酰氯的消旋杂环胺的非对映选择性酰化及其结构类似物

  摘要：

  通过N-甲苯磺酰基-（S）-脯氨酰氯的非对映选择性酰化反应得到外消旋胺（2,3-二氢-4H-1,4-苯并恶嗪和1,2,3,4-四氢喹啉衍生物）的动力学拆分的比较研究并进行了结构类似物。考察了拆分剂结构对杂环胺酰化立体选择性的影响。在用带有构象受限的吡咯烷环和在氮原子上的保护基团上的芳族取代基的酰氯酰化的情况下，可获得最高的立体选择性。

  DOI：

  10.1007/s10593-014-1538-8

文献信息

• Cephalosporin compounds
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0376724A3

  公开（公告）日：1991-09-25

  Cephalosporin compounds of the formula: wherein R1 is amino or protected amino; R2 is substituted or unsubstituted heterocyclic group having 1 - 3 hetero atoms selected from oxygen and sulphur; R3 is carboxyl or protected carboxyl; R4 is nucleophilic compound residue; R5 is carboxyl, protected carboxyl and -COO-, a pharmaceutically acceptable salt thereof and their synthetic intermediate of the formula:wherein R11 is amino or protected amino; R2 is substituted or unsubstituted heterocyclic group having 1 - 3 hetero atoms selected from oxygen and sulfur; R3 is carboxyl or protected carboxyl; -COOY is carboxyl or protected carboxyl. Said cephalosporin compound is useful as antibacterial agent.

  头孢菌素类化合物，其通式为：其中R1为氨基或保护的氨基；R2为含有1至3个选自氧和硫的杂原子的取代或未取代的杂环基团；R3为羧基或保护的羧基；R4为亲核化合物残基；R5为羧基、保护的羧基和-COO-，以及它们的药学上可接受的盐和其合成中间体的通式：其中R11为氨基或保护的氨基；R2为含有1至3个选自氧和硫的杂原子的取代或未取代的杂环基团；R3为羧基或保护的羧基；-COOY为羧基或保护的羧基。所述头孢菌素化合物可作为抗菌剂使用。
• Synthesis and Biological Evaluation of Alkyl, Alkoxy, Alkylthio, or Amino-Substituted 2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones.
  作者：Hirozumi INOUE、Mikihiko KONDA、Tomiki HASHIYAMA、Hisao OTSUKA、AKishige WATANABE、Mitsunori GAINO、Kaoru TAKAHASHI、Tadamasa DATE、Kimio OKAMURA、Mikio TAKEDA、Hiroshi NARITA、Sakae MURATA、AKio ODAWARA、Haruhiko SASAKI、Taku NAGAO

  DOI：10.1248/cpb.45.1008

  日期：——

  5-benzothiazepine skeleton were synthesized and their vasodilating, antihypertensive, and platelet aggregation-inhibitory activities were investigated. (-)-cis-3-Acetoxy-5-[2-(di-methylamino) ethyl]-2,3-dihydro-8-methyl-2-(4-methylphenyl)-1,5-benzothiazepin- 4(5H)-one ((-)-13e) was selected for further studies as a potent inhibitor of platelet aggregation.

  合成了被1,5-苯并噻氮平骨架的稠合苯环上的烷基，烷氧基，烷硫基，羟基或氨基取代的2,3-二氢-1,5-苯并噻唑啉-4（5H）-并使其血管舒张，降压和血小板聚集抑制活性进行了研究。（-）-顺-3-乙酰氧基-5- [2-（二甲基氨基）乙基] -2,3-二氢-8-甲基-2-（4-甲基苯基）-1,5-苯并噻嗪-4（5H ）-（（-）-13e）被选作血小板聚集的有效抑制剂进行进一步研究。
• Naphtho thiazine (or oxaline) derivatives and preparations thereof
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US05246929A1

  公开（公告）日：1993-09-21

  Thiazine (or oxazine) derivatives of the formula [I]: ##STR1## wherein R.sup.1 and R.sup.2 are both H or form a naphthalene ring together with the benzene ring; R.sup.3 and R.sup.4 are both H, or one of them is halogen and another is H; X is S or O; R.sup.5 and R.sup.6 are each i) H, ii) lower alkyl, iii) cycloalkyl, iv) substituted phenyl, v) naphthyl, vi) lower alkyl which is substituted by substituted or unsubstituted phenyl, or vii) S-containing heterocyclic group; one of Z.sup.1 and Z.sup.2 is O and another is H.sub.2 ; A is lower alkylene; R.sup.7 and R.sup.8 are each i) H, ii) lower alkyl, iii) lower alkenyl, iv) lower alkynyl, or v) lower alkyl which is substituted by substituted or unsubstituted phenyl, or both form together N-containing heterocyclic group; provided that when both of R.sup.1 and R.sup.2 are H, Z.sup.2 is O and either one of R.sup.5 and R.sup.6 is substituted phenyl, naphthyl or S-containing heterocyclic group, or their salts, which have calcium antagonistic activity within the cerebral tissues and are useful for prophylaxis and treatment of ischemic encephalopathia and/or cerebral neurocyte dyscrasia, and process for preparing said compounds.

  吡嗪（或噁嗪）衍生物的化学式[I]：其中R.sup.1和R.sup.2均为H或者与苯环一起形成一个萘环；R.sup.3和R.sup.4均为H，或其中一个为卤素，另一个为H；X为S或O；R.sup.5和R.sup.6分别为i）H，ii）较低烷基，iii）环烷基，iv）取代苯基，v）萘基，vi）受取代或未取代苯基取代的较低烷基，或者vii）含S的杂环基；Z.sup.1和Z.sup.2中的一个为O，另一个为H.sub.2；A为较低烷基；R.sup.7和R.sup.8分别为i）H，ii）较低烷基，iii）较低烯基，iv）较低炔基，或v）受取代或未取代苯基取代的较低烷基，或者两者一起形成含N的杂环基；但当R.sup.1和R.sup.2均为H时，Z.sup.2为O，且R.sup.5和R.sup.6中的任一者为取代苯基、萘基或含S的杂环基时，或它们的盐，具有对大脑组织内钙拮抗活性，并且适用于缺血性脑病和/或脑神经细胞异常的预防和治疗的化合物的制备方法。
• Thiazine (or oxazine) derivatives and preparation thereof
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US05496815A1

  公开（公告）日：1996-03-05

  Thiazine derivatives of the formula [I]: ##STR1## wherein R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are each hydrogen atom; R.sup.3 is hydrogen atom or a halogen atom; X is sulfur atom; R.sup.6 is naphthyl, a sulfur-containing monoheterocyclic group or a substituted phenyl; Z.sup.1 is two hydrogen atoms; Z.sup.2 is oxygen atom; A is a lower alkylene; R.sup.7 and R.sup.8 are the same or different and are each i) hydrogen atom, ii) a lower alkyl, iii) a lower alkenyl, iv) a lower alkynyl, or v) a lower alkyl which is substituted by a substituted phenyl, or both form together with the adjacent nitrogen atom a nitrogen-containing monoheterocyclic group; except for the compound [I] wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each hydrogen atom, X is sulfur atom, R.sup.6 is a halogenophenyl, Z.sup.1 is two hydrogen atoms, Z.sup.2 is oxygen atom, A is a lower alkylene, R.sup.7 and R.sup.8 are the same or different and each a lower alkyl; or a pharmaceutically acceptable salt thereof, which have calcium antagonistic activity within the cerebral tissues and are useful for prophylaxis and treatment of ischemic encephalopathia.

  式[I]的噻嗪衍生物：其中R.sup.1、R.sup.2、R.sup.4和R.sup.5分别是氢原子；R.sup.3是氢原子或卤原子；X是硫原子；R.sup.6是萘基、含硫的单杂环基团或取代苯基；Z.sup.1是两个氢原子；Z.sup.2是氧原子；A是较低的烷基；R.sup.7和R.sup.8相同或不同，分别是i）氢原子，ii）较低烷基，iii）较低烯基，iv）较低炔基，或v）被取代苯基取代的较低烷基，或者两者与相邻氮原子一起形成含氮的单杂环基团；除了式[I]中R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5分别是氢原子，X是硫原子，R.sup.6是卤代苯基，Z.sup.1是两个氢原子，Z.sup.2是氧原子，A是较低的烷基，R.sup.7和R.sup.8相同或不同，分别是较低烷基；或者其药学上可接受的盐，具有在脑组织内的钙拮抗活性，并且用于预防和治疗缺血性脑病。
• Synthesis of halogen-substituted 1,5-benzothiazepine derivatives and their vasodilating and hypotensive activities
  作者：Hirozumi Inoue、Mikihiko Konda、Tomiki Hashiyama、Hisao Otsuka、Kaoru Takahashi、Mitsunori Gaino、Tadamasa Date、Keiichi Aoe、Mikio Takeda

  DOI：10.1021/jm00106a032

  日期：1991.2

  its derivatives (2) with halogen substituents on the fused benzene ring were synthesized. These compounds were evaluated for their effects on vertebral and coronary blood flows and antihypertensive activity. The structure-activity relationships are discussed. The 8-chloro derivative ((+)-2b), the most potent compound in this series, was selected for clinical evaluation as a cerebral vasodilating and

  为了提高地尔硫卓（1）的作用效果和持续时间，合成了1，5-苯并硫氮杂卓钙通道阻滞剂，其衍生物（2）在稠合的苯环上具有卤素取代基。评估了这些化合物对椎骨和冠状动脉血流以及降压活性的影响。讨论了构效关系。选择该系列中最有效的化合物8-氯衍生物（（+）-2b）作为脑血管扩张和降压药进行临床评估。