1-(对氨基苯基)环戊烷羧酸 | 91640-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(对氨基苯基)环戊烷羧酸
• 英文名称: 1-(p-aminophenyl)cyclopentanecarboxylic acid
• 英文别名: 1-(4-amino-phenyl)cyclopentanecarboxylic acid；1-(4-aminophenyl)cyclopentanecarboxylic acid；1-<4-Amino-phenyl>-cyclopentan-carbonsaeure-(1)；1-(4-aminophenyl)cyclopentane-1-carboxylic acid
• CAS: 91640-63-0
• 化学式: C₁₂H₁₅NO₂
• mdl: MFCD00805863
• 分子量: 205.257
• InChiKey: YIQOEBGLMQXPHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  405.9±38.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(对氨基苯基)环戊烷羧酸 在 盐酸 、 氯化亚砜 、 sodium carbonate 、 sodium nitrite 作用下， 以 苯 为溶剂， 反应 9.5h， 生成 2-(diethylamino)ethyl 1-(p-cyanophenyl)cyclopentanecarboxylate
  参考文献：
  名称：

  Muscarinic receptor binding profile of para-substituted caramiphen analogs

  摘要：

  Para-substituted analogues of the antimuscarinic agent caramiphen were synthesized and evaluated for their ability to bind to the M1 and M2 subtypes of the muscarinic receptor. The purpose of the set was to look for a possible relationship in binding affinity or receptor subtype selectivity with aromatic substituent parameters such as Hammett's-sigma or Hansch's pi-values. It is felt this could be determined initially with only four properly chosen substituents. In this approach, substituents were chosen which have an extreme value for sigma and for pi, in a positive and negative direction, in all combinations. The substituents chosen for examination were amino (-sigma, -pi); 1-pyrrolidinyl (-sigma, +pi); 1-tetrazolyl (+sigma, -pi), and iodo (+sigma, +pi). It was determined in this research that caramiphen binds with high affinity (K(i) = 1.2 nM) and is selective for the M1 over M2 muscarinic receptor subtype (26-fold). An examination of para-substitution reveals that compounds with electron-withdrawing (+sigma) substituents showed M1 selectivity, while the derivatives with electron-donating groups (-sigma) were nonselective in the binding assays. On the basis of this finding, the nitro and cyano derivatives were prepared and found to be M1 selective. The +sigma derivatives showed a decrease in M2 affinity while the p-nitro and p-iodo derivatives retained approximately equal affinity as caramiphen for the M1 site. The nitro- and iodocaramiphen derivatives were as potent (M1, K(i) = 5.52 and 2.11 nM, respectively) and showed a greater selectivity of M1 over M2 binding than the M1 prototypical agent pirenzepine (M1, K(i) = 5.21 nM).

  DOI：

  10.1021/jm00114a005
• 作为产物：
  描述：

  1-(4-氨基苯基)环戊甲腈 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 9.0h， 以100%的产率得到1-(对氨基苯基)环戊烷羧酸
  参考文献：
  名称：

  WO2008/117175

  摘要：

  公开号：
• 作为试剂：
  描述：

  1-(4-硝基苯基)环戊烷羧酸 、 钠 、 盐酸 、 potassium carbonate 、 甲氧基乙酰氯 在 氯化镍 三苯基膦 、 ice 、 1-(对氨基苯基)环戊烷羧酸 、 乙醚 作用下， 以 水 、 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以to afford 25.4 g (yield 91.6%) of the desired compound as white crystals的产率得到1-(4-methoxyacetylaminophenyl)cyclopentanecarboxylic acid
  参考文献：
  名称：

  13-substituted milbemycin derivatives, their preparation and their use against insects and other pests

  摘要：

  化合物的式子(I)及其盐：其中R1代表甲基、乙基、异丙基或s-丁基；R2代表氢或烷基。R3代表氢、可选取代的烷酰基、可选取代的烯酰基、可选取代的炔酰基、烷基磺酰基或烷氧羰基，或者R2和R3与它们连接的氮原子一起形成一个饱和的、可选取代的4到6元杂环环基。-a-基团与它连接的碳原子一起形成一个3到6元的环烷基团。这些化合物具有驱虫、杀螨和杀虫活性。

  公开号：

  US06653342B2

文献信息

• NOVEL BENZAMIDE DERIVATIVES AS MODULATORS OF THE FOLLICLE STIMULATING HORMONE
  申请人：Bonnet Beatrice

  公开号：US20100249123A1

  公开（公告）日：2010-09-30

  The present invention provides new compounds of formula I, wherein Q, R 1 , R 2 , R 4 , R 5 , R 6 , X i , R 7 , R 8 , M and G 1 n are defined as in formula I; invention compounds are modulators of follicle-stimulating hormone—(“FSH”) which are useful for male and female contraception as well as other disorders modulated by FSH receptor.

  本发明提供了新的I式化合物，其中Q、R1、R2、R4、R5、R6、Xi、R7、R8、M和G1n如I式中所定义；发明化合物是促卵泡素-（“FSH”）的调节剂，可用于男性和女性避孕以及其他受FSH受体调节的疾病。
• Synthesis of a potential M1 muscarinic agent [76Br]bromocaramiphen
  作者：V. Strijckmans、D. H. Hunter、F. Dolle、C. Coulon、C. Loc'h、B. Mazière

  DOI：10.1002/(sici)1099-1344(199605)38:5<471::aid-jlcr854>3.0.co;2-q

  日期：1996.5

  [Br-76]bromocaramiphen was prepared from the iodo-analogue by a Cu+ nucleophilic bromodeiodination exchange. The radiolabelling yield was 40-45%. The radiochemical and chemical purities assessed by radio-TLC and HPLC were 98%. The precursor, iodocaramiphen, was synthesized from commercially available 1-phenylcyclopentanecarboxylic acid with a 10% overall yield in a 5 step procedure. This synthesis includes the formation of 1-(p-nitrophenyl)-, 1-(p-aminophenyl)- and 1-(p-iodophenyl) cyclopentane carboxylic acid. In vivo studies in rats showed high uptake in brain. A 10% decrease was observed by coinjecting with the radiotracer a cold load of QNB, a non subtype selective muscarinic ligand. The metabolite study performed in the polls tissues indicated that there was still 92% of unchanged radiotracer 30 min p.i. After coinjection of dextrometorphan, a sigma ligand, a reduction of the radioactivity uptake by 20 to 27% was observed in the pens, the colter, the striatum and the cerebellum. These data suggest that [Br-76]bromocaramiphen is not a potential probe for investigating the status of central M(1) muscarinic receptors because of its high lipophilicity (log P-7.4 = 2.4) and its affinity for sigma sites.
• 13-SUBSTITUTED MILBEMYCIN DERIVATIVES, THEIR PREPARATION AND THEIR USE AGAINST INSECTS AND OTHER PESTS
  申请人：Sankyo Lifetech Company Limited

  公开号：EP1276748B1

  公开（公告）日：2006-01-11
• US6653342B2
  申请人：——

  公开号：US6653342B2

  公开（公告）日：2003-11-25
• [EN] ARYLETHANOLAMINE DERIVATIVES AND THEIR USE AS AGONISTS OF ATYPICAL BETA-ADRENOCEPTORS<br/>[FR] DERIVES D'ARYLETHANOLAMINE ET LEUR UTILISATION EN TANT QU'AGONISTES DES BETA-RECEPTEURS ADRENERGIQUES ATYPIQUES
  申请人：GLAXO GROUP LIMITED

  公开号：WO1997021666A1

  公开（公告）日：1997-06-19

  (EN) The present invention relates to phenethanolamine derivatives of formula (I), wherein R1 represents an aryl group optionally substituted by one or more substituents selected from halogen, hydroxy, C1-6alkoxy, C1-6alkyl, nitro, cyano, hydroxymethyl and trifluoromethyl; R2 represents hydrogen or C1-6alkyl; R3 represents a group (A) where the aromatic ring may be optionally substituted by up to four substituents selected from C1-6alkyl, halogen, trifluoromethyl, and C1-6alkoxy; R4 represents hydrogen, or C1-6alkyl; R5 represents CO2R8, C1-6alkylCO2R16, CONR9R10, NHCONR11R12, SO2NHR13, P(O)(OR14)2, SO3H, C1-6alkylSO3H, NHSO2R15, NHCOR17 or tetrazol-5-yl; R6 and R7 independently represent hydrogen, C1-6alkyl, trifluoromethyl, CN, OH, CO2R18, CH2CO2R19, or R6 and R7 form a 5-6 membered cycloalkyl ring; R8 represents hydrogen, or C1-6alkyl; R9 represents hydrogen, C1-6alkyl, or C1-6alkylOR20; R10, R11, R12, R14-R16, and R18-R20 each independently represent hydrogen, or C1-6alkyl; R13 represents C1-6alkyl or trifluoromethyl; R17 represents C1-6alkyl or trifluoromethyl; with the proviso that when R6 and R7 are both hydrogen, R8 is other than hydrogen; and physiologically acceptable derivatives thereof; to processes for their preparation; and their use in the treatment of conditions susceptible of amelioration by an atypical beta-adrenoceptor agonist.(FR) La présente invention se rapporte à des dérivés de phénéthanolamine de la formule (I), ainsi qu'à des dérivés de ceux-ci, acceptables sur le plan physiologique. Dans cette formule, R1 représente un groupe aryle éventuellement substitué par un ou plusieurs substituants choisis parmi halogène, hydroxy, alcoxy C1-6, alkyle C1-6, nitro, cyano, hydroxyméthyle et trifluorométhyle; R2 représente hydrogène ou alkyle C1-6; R3 représente un groupe (A) où le noyau aromatique peut être éventuellement substitué par au maximum quatre substituants choisis parmi alkyle C1-6, halogène, trifluorométhyle et alcoxy C1-6, R4 représente hydrogène ou alkyle C1-6, R5 représente CO2R8, alkyle C1-6CO2R16, CONR9R10, NHCONR11R12, SO2NHR13, P(O)(OR14)2, SO3H, alkyle C1-6SO3H, NHSO2R15, NHCOR17 ou tétrazol-5-yle, R6 et R7 représentent indépendamment hydrogène, alkyle C1-6, trifluorométhyle, CN, OH, CO2R18, CH2CO2R19, ou bien R6 et R7 forment un noyau cycloalkyle possédant 5 à 6 chaînons, R8 représente hydrogène ou alkyle C1-6, R9 représente hydrogène, alkyle C1-6 ou alkyle C1-6OR20, R10, R11, R12, R14-R16 et R18-R20 représentent chacun indépendamment hydrogène ou alkyle C1-6, R13 représente alkyle C1-6 ou trifluorométhyle, R17 représente alkyle C1-6 ou trifluorométhyle, à la condition que lorsque R6 et R7 représentent tous deux hydrogène, R8 ne représente pas hydrogène. On décrit également des procédés de préparation de ces dérivés ainsi que leur utilisation dans le traitement d'états pathologiques susceptibles d'être améliorés par un agoniste des bêta-récepteurs adrénergiques atypiques.