N-(2-naphthylsulfonyl)-(S)-proline | 91872-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-naphthylsulfonyl)-(S)-proline
• 英文别名: N-(2-naphthylsulfonyl)-L-proline；2-Naphthylsulfonyl-L-prolin；1-(naphthalene-2-sulfonyl)-L-proline；1-(Naphthalin-2-sulfonyl)-L-prolin；(S)-1-(2-naphthylsulfonyl)pyrrolidine-2-carboxylic acid；(S)-1-(Naphthalen-2-ylsulfonyl)pyrrolidine-2-carboxylic acid；(2S)-1-naphthalen-2-ylsulfonylpyrrolidine-2-carboxylic acid
• CAS: 91872-30-9
• 化学式: C₁₅H₁₅NO₄S
• mdl: MFCD01080692
• 分子量: 305.354
• InChiKey: GVNYVKRDASNULU-AWEZNQCLSA-N

物化性质

• 熔点：
  130-133 °C
• 沸点：
  549.9±60.0 °C(Predicted)
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-naphthylsulfonyl)-(S)-proline 在 TEA 、 硫化氢 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 乙酸乙酯 、 三乙胺 为溶剂， 反应 116.0h， 生成 (S)-1-(Naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid [2-oxo-2-pyrrolidin-1-yl-1-(4-thiocarbamoyl-benzyl)-ethyl]-amide
  参考文献：
  名称：

  Voigt; Wagner, Pharmazie, 1986, vol. 41, # 4, p. 233 - 235

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (2S)-1-naphthalen-2-ylsulfonylpyrrolidine-2-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2-naphthylsulfonyl)-(S)-proline
  参考文献：
  名称：

  Small molecule antagonists of the CC chemokine receptor 4 (CCR4)

  摘要：

  The identification, optimization, and structure-activity relationship (SAR) of small-molecule CCR4 antagonists is described. An initial screening hit with micromolar potency was identified that was optimized to sub-micromolar binding potency by enantiomer resolution, halogenation of the naphthalene ring, and extension of the alkyl chain linker between the central piperidine ring and the terminal aryl group. An antagonist was identified that showed good cross-reactivity against the mouse receptor and inhibited CCR4-based cell recruitment in dose-dependent fashion. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.03.030

文献信息

• Nitrile derivatives that inhibit cathepsin K
  申请人：——

  公开号：US20010008901A1

  公开（公告）日：2001-07-19

  Compounds of the formula: 1 wherein R 1 to R 7 and Y are as defined in the specification, and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof, are useful for treating diseases associated with cystein proteases, such as osteoporosis, osteoarthritis, rheumatoid arthritis, tumor metastasis, glomerulonephritis, atherosclerosis, myocardial infarction, angina pectoris, instable angina pectoris, stroke, plaque rupture, transient ischemic attacks, amaurosis fugax, peripheral arterial occlusive disease, restenosis after angioplasty and stent placement, abdominal aortic aneurysm formation, inflammation, autoimmune disease, malaria, ocular fundus tissue cytopathy and respiratory disease.

  该公式化合物：其中R1到R7和Y如规范中定义，并且其药用盐和/或药用酯是用于治疗与半胱氨酸蛋白酶相关的疾病，如骨质疏松症、骨关节炎、类风湿性关节炎、肿瘤转移、肾小球肾炎、动脉粥样硬化、心肌梗死、心绞痛、不稳定性心绞痛、中风、斑块破裂、短暂性缺血性发作、瞬间性视网膜动脉阻塞、外周动脉闭塞性疾病、血管成形术和支架植入术后再狭窄、腹主动脉瘤形成、炎症、自身免疫疾病、疟疾、眼底组织细胞病变和呼吸道疾病的有用化合物。
• Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Tosyl-(S)-Prolyl Chloride and its Structural Analogs
  作者：S. A. Vakarov、D. A. Gruzdev、E. N. Chulakov、L. Sh. Sadretdinova、M. A. Ezhikova、M. I. Kodess、G. L. Levit、V. P. Krasnov

  DOI：10.1007/s10593-014-1538-8

  日期：2014.9

  resolution of racemic amines (2,3-dihydro-4H-1,4-benzoxazine and 1,2,3,4-tetrahydroquinoline derivatives) via diastereoselective acylation with N-tosyl-(S)-prolyl chloride and its structural analogs was performed. The effect of resolving agent structure on the stereoselectivity of heterocyclic amine acylation was examined. The highest stereoselectivity was achieved in the case of acylation with acyl chlorides

  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。
• [EN] AZAPHENYLALANINE DERIVATIVES AND THEIR USE AS ANTITHROMBOTIC AGENTS<br/>[FR] DERIVES D'AZAPHENYLALANINE ET LEUR UTILISATION EN TANT QU'AGENTS ANTITHROMBONTIQUES
  申请人：LEK PHARMACEUTICALS

  公开号：WO2004067522A1

  公开（公告）日：2004-08-12

  Novel azaphenylalanine derivatives of the formula I and pharmaceutically acceptable salts thereof are described wherein the substituents have the meanings as specified in the description. The compounds are useful as anticoagulants.

  描述了一种公式I的新型假丝氨酸衍生物和其药用可接受的盐，其中取代基的含义如描述中所指定。这些化合物可用作抗凝剂。
• PROLINE SULFONAMIDE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
  申请人：Boss Christoph

  公开号：US20130150424A1

  公开（公告）日：2013-06-13

  The present invention relates to (S)-proline sulfonamide compounds of formula (I) wherein R 1 and R 2 are as described in the description, or pharmaceutically acceptable salts thereof, for use in the prevention or treatment of diseases or disorders related to the orexin system. The present invention also relates to the use of (S)-proline sulfonamide compounds of formula (II) as pharmaceuticals, to pharmaceutical compositions comprising compounds of formula (II), and especially their use in the prevention or treatment of diseases or disorders related to the orexin system.

  本发明涉及公式（I）中的（S）-脯氨酸磺酰胺化合物，其中R1和R2如说明书中所述，或其药学上可接受的盐，用于预防或治疗与促进素系统相关的疾病或障碍。本发明还涉及使用公式（II）中的（S）-脯氨酸磺酰胺化合物作为药物，制备含有公式（II）化合物的药物组合物，特别是它们在预防或治疗与促进素系统相关的疾病或障碍方面的使用。
• Process for the preparation of 8-hydroxy-5-[(1R)-1-hydroxy-2[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]-2(1H)-quinolinone monohydrochloride
  申请人：CHIESI FARMACEUTICI S.p.A.

  公开号：EP1953143A1

  公开（公告）日：2008-08-06

  The invention relates to a process for the preparation of 8-hydroxy-5-[(1R)-1-hydroxy-2 [[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]-2(1H)-quinolinone monohydrochloride of formula (I). Useful intermediates in the process are also disclosed.

  本发明涉及一种制备式为(I)的8-羟基-5-[(1R)-1-羟基-2[[(1R)-2-(4-甲氧基苯基)-1-甲基乙基]氨基]乙基]-2(1H)-喹啉酮单盐酸盐的方法。本方法还揭示了有用的中间体。