3-(4-methanesulphonylamidophenyl)propanoic acid | 103790-23-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(4-methanesulphonylamidophenyl)propanoic acid
• 英文别名: 3-(4-(methylsulfonamido)phenyl)propanoic acid；3-[4-[(methanesulfonyl)amino]phenyl]propionic acid；3-[4-(methanesulfonamido)phenyl]propanoic acid
• CAS: 103790-23-4
• 化学式: C₁₀H₁₃NO₄S
• 分子量: 243.284
• InChiKey: PKVXOQIKRLHBPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methanesulphonylamidophenyl)propanoic acid 在 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 N-(4-(3-(2-(3,4-dichlorophenylamino)ethylamino)-propyl)phenyl)methanesulfonamide hydrochloride
  参考文献：
  名称：

  Synthesis, structural activity-relationships, and biological evaluation of novel amide-based allosteric binding site antagonists in NR1A/NR2B N-methyl-d-aspartate receptors☆

  摘要：

  The synthesis and structure-activity relationship analysis of a novel class of amide-based biaryl NR2B-selective NMDA receptor antagonists are presented. Some of the studied compounds are potent, selective, non-competitive, and voltage-independent antagonists of NR2B-containing NMDA receptors. Like the founding member of this class of antagonists (ifenprodil), several interesting compounds of the series bind to the amino terminal domain of the NR2B subunit to inhibit function. Analogue potency is modulated by linker length, flexibility, and hydrogen bonding opportunities. However, unlike previously described classes of NR2B-selective NMDA antagonists that exhibit off-target activity at a variety of monoamine receptors, the compounds described herein show much diminished effects against the hERG channel and alpha(1)-adrenergic receptors. Selections of the compounds discussed have acceptable half-lives in vivo and are predicted to permeate the blood-brain barrier. These data together suggest that masking charged atoms on the linker region of NR2B-selective antagonists can decrease undesirable side effects while still maintaining on-target potency. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.05.085
• 作为产物：
  描述：

  3-(4-氨基苯基)丙酸 在 甲醇 、 氯化亚砜 、 sodium hydroxide 作用下， 以 吡啶 为溶剂， 反应 1.17h， 生成 3-(4-methanesulphonylamidophenyl)propanoic acid
  参考文献：
  名称：

  NMDA RECEPTOR ANTAGONISTS FOR NEUROPROTECTION

  摘要：

  公开号：

  EP2170334B1

文献信息

• BRADYKININ RECEPTOR AGONISTS AND USES THEREOF TO TREAT OCULAR HYPERTENSION AND GLAUCOMA
  申请人：Combrink Keith D.

  公开号：US20120046285A1

  公开（公告）日：2012-02-23

  The invention provides compositions and methods for treating and/or preventing ocular disorders associated with increased intraocular pressure. In particular, the compounds are bradykinin agonists.

  这项发明提供了用于治疗和/或预防与眼内压增高相关的眼部疾病的组合物和方法。具体来说，这些化合物是激肽酶激动剂。
• Antiarrhythmic N-aminoalkylene alkyl and aryl sulfonamides
  申请人：The Upjohn Company

  公开号：US05155268A1

  公开（公告）日：1992-10-13

  The present invention provides novel sulfonanilide and benzene-alkylaminium compounds which are the products of processes utilizing novel intermediates. Both the novel compounds and the novel intermediates are useful for the therapeutic or prophylactic treatment of arrhythmic activity.

  本发明提供了新型磺酰苯胺和苯基-烷基铵化合物，这些化合物是利用新型中间体的过程产生的产物。这些新型化合物和新型中间体均可用于治疗或预防心律不齐活动。
• NMDA Receptor Antagonists for Neuroprotection
  申请人：Liotta Dennis C.

  公开号：US20090253710A1

  公开（公告）日：2009-10-08

  Provided are compounds, pharmaceutical compositions and methods of treatment or prophylaxis of disorders associated with NMDA receptor activity, including neuropathic pain, stroke, traumatic brain injury, epilepsy, and related neurologic events or neurodegeneration. Compounds are of the general Formula I, or a pharmaceutically acceptable salt, ester, prodrug or derivative thereof are provided: wherein: each (L) k -Ar 1 is a substituted or unsubstituted, mono or bicyclic aryl or heteroaryl; W is a bond, alkyl, or alkenyl; X is a bond, NR 1 or O and each R 1 and R 2 is independently H, alkyl, alkenyl or aralkyl or R 1 and R 2 taken together form a 5-8 membered ring; R 3− R 6 are selected from certain specific substituents or a carbonyl; Y is a bond, O, S, SO, SO 2 , CH 2 , NH, N(alkyl), or NHC(═O); and Z is OH, NR 6 R 7 , NR 8 SO 2 (alkyl), NR 8 C(O)NR 6 R 7 , NR 8 C(O)O(alkyl), NR 8 -dihydrothiazole, or NR 8 -dihydroimidazole or wherein Z can fuse with Ar 2 to form selected heterocycles.

  提供了与NMDA受体活性相关的疾病治疗或预防的化合物、制药组合物和方法，包括神经病理性疼痛、中风、创伤性脑损伤、癫痫和相关的神经事件或神经退行性疾病。提供了通式I的化合物或其药学上可接受的盐、酯、前药或衍生物: 其中：每个（L）k-Ar1是取代或未取代的、单环或双环芳基或杂环芳基；W是键、烷基或烯基；X是键、NR1或O，每个R1和R2是独立的H、烷基、烯基或芳基烷基，或R1和R2共同形成5-8成员环；R3-R6选自特定的取代基或羰基；Y是键、O、S、SO、SO2、CH2、NH、N（烷基）或NHC（═O）；Z是OH、NR6R7、NR8SO2（烷基）、NR8C（O）NR6R7、NR8C（O）O（烷基）、NR8-二氢噻唑或NR8-二氢咪唑，或Z可以与Ar2融合形成选择的杂环。
• Bradykinin receptor agonists and uses thereof to treat ocular hypertension and glaucoma
  申请人：Alcon Research, Ltd.

  公开号：US08252793B2

  公开（公告）日：2012-08-28

  The invention provides compositions and methods for treating and/or preventing ocular disorders associated with increased intraocular pressure. In particular, the compounds are bradykinin agonists.

  该发明提供了用于治疗和/或预防与眼内压增高相关的眼部疾病的组合物和方法。具体来说，这些化合物是激动肽酶激动剂。
• Indole derivatives having a selective vasoconstrictor activity
  申请人：GLAXO GROUP LIMITED

  公开号：EP0240096A1

  公开（公告）日：1987-10-07

  Compounds are disclosed of formula (I): wherein R, represents halogen, C1 3 alkoxy, or a group R6R7NCO(CH2)p-, R6CONH(CH2)P-, R6R7NSO2(CH2)p-, or R8SO2NH(CH2)p - (where R6 and R7, each independently represents hydrogen or C, 3 alkyl, Ra represents C1 3 alkyl and p is zero or 1); R2 represents hydrogen or C, 3 alkyl; R3 represents hydrogen or C, 3 alkyl; R4 and R5 each independently represents hydrogen, a C1 3 alkyl or a 2-propenyl group; A represents -CO- or -SO2-; n represents an integer from 2 to 5; an m represents zero or an integer from 1 to 4; and physiologically acceptable salts and solvates (e.g. hydrates) thereof. The compounds have potent and selective vasoconstrictor activity and are indicated as useful for the treatment of migraine. The compounds may be formulated as pharmaceutical compositions with pharmaceutically acceptable carriers or excipients for administration by any suitable means. Various methods for the preparation of the compounds are disclosed.

  公开了式(I)化合物： 其中 R 代表卤素、C1 3 烷氧基或一个基团 R6R7NCO(CH2)p-, R6CONH(CH2)P-, R6R7NSO2(CH2)p-、 或 R8SO2NH（CH2）p-（其中 R6 和 R7 各自独立地代表氢或 C，3 烷基，Ra 代表 C1 3 烷基，p 为 0 或 1）； R2 代表氢或 C，3 烷基； R3 代表氢或 C，3 烷基； R4 和 R5 各自独立地代表氢、 C1 3 烷基或 2-丙烯基； A 代表-CO-或-SO2-； n 代表 2 至 5 的整数；m 代表零或 1 至 4 的整数；及其生理上可接受的盐和溶液（如水合物）。 这些化合物具有强效和选择性血管收缩活性，可用于治疗偏头痛。这些化合物可与药学上可接受的载体或赋形剂配制成药物组合物，以任何合适的方式给药。公开了制备这些化合物的各种方法。