1-(4-碘苯基)环戊烷羧酸 | 135569-28-7

• 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-(4-碘苯基)环戊烷羧酸
• 英文名称: 1-(p-iodophenyl)cyclopentanecarboxylic acid
• 英文别名: 1-(4-iodophenyl)cyclopentanecarboxylic acid；1-(4-iodophenyl)cyclopentane-1-carboxylic acid
• CAS: 135569-28-7
• 化学式: C₁₂H₁₃IO₂
• 分子量: 316.139
• InChiKey: SLQJYMQCVGGGCO-UHFFFAOYSA-N

物化性质

• 沸点：
  397.1±35.0 °C(Predicted)
• 密度：
  1.702±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-碘苯基)环戊烷羧酸 在 氯化亚砜 、 1,3-双(二苯基膦)丙烷 、 水 、 palladium diacetate 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.25h， 生成 4-(1-{[(2R)-2-(1H-indazol-4-ylcarbamoyl)pyrrolidin-1-yl]carbonyl}cyclopentyl)benzoic acid
  参考文献：
  名称：

  EP3643703

  摘要：

  公开号：
• 作为产物：
  描述：

  1-(对氨基苯基)环戊烷羧酸 在 盐酸 、 potassium iodide 、 sodium nitrite 作用下， 生成 1-(4-碘苯基)环戊烷羧酸
  参考文献：
  名称：

  Synthesis of a potential M1 muscarinic agent [76Br]bromocaramiphen

  摘要：

  [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.

  DOI：

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

文献信息

• [EN] 1,1-DISUBSTITUTED CYCLOALKYL DERIVATIVES AS FACTOR XA INHIBITORS<br/>[FR] DERIVES CYCLOALKYLES 1,1-DISUBSTITUES UTILISES EN TANT QU'INHIBITEURS DU FACTEUR XA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003099276A1

  公开（公告）日：2003-12-04

  The present application describes 1,1-disubstituted cycloalkyl compounds and derivatives thereof, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of factor Xa.

  本申请描述了1,1-二取代环烷基化合物及其衍生物，或其药用可接受的盐形式，这些化合物对于Xa因子的抑制剂具有用处。
• EP300/CREBBP INHIBITOR
  申请人：Daiichi Sankyo Co., Ltd.

  公开号：EP3643703A1

  公开（公告）日：2020-04-29

  The present invention provides a compound having excellent histone acetyltransferase inhibitory activity against EP300 and/or CREBBP, or a pharmacologically acceptable salt thereof. The compound is represented by the following formula (1) or a pharmacologically acceptable salt thereof: wherein ring Q1, ring Q2, R1, R2, R3 and R4 respectively have the same meanings as defined in the specification.

  本发明提供了一种对 EP300 和/或 CREBBP 具有优异组蛋白乙酰转移酶抑制活性的化合物或其药理学上可接受的盐。该化合物由下式（1）或其药理学上可接受的盐表示： 其中，环 Q1、环 Q2、R1、R2、R3 和 R4 分别具有本说明书中定义的相同含义。
• Muscarinic receptor binding profile of para-substituted caramiphen analogs
  作者：Robert L. Hudkins、Diane L. DeHaven-Hudkins、James F. Stubbins

  DOI：10.1021/jm00114a005

  日期：1991.10

  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).
• Novel (4-Phenylpiperidinyl)- and (4-Phenylpiperazinyl)alkyl-Spaced Esters of 1-Phenylcyclopentanecarboxylic Acids as Potent .sigma.-Selective Compounds
  作者：Robert L. Hudkins、Richard B. Mailman、Diane L. DeHaven-Hudkins

  DOI：10.1021/jm00039a008

  日期：1994.6

  A series of novel 4-phenylpiperidinyl and (4-phenylpiperazinyl) alkyl 1-phenylcyclopentanecarboxylates was synthesized and evaluated for affinity at sigma(1) and sigma(2) sites by inhibition of [H-3]-(+)-pentazocine (PENT) and [H-3]-1,3-di(2-tolyl)guanidine (DTG) binding in guinea pig brain. The phenylpiperidines were more potent sigma ligands than the corresponding piperazines. Structural modifications varying the optimal spatial distance between the piperidine nitrogen and ester functions led to the identification of the propyl compound 24 ([H-3]PENT K-i = 0.50 nM; [H-3]DTG K-i = 1.17 nM) and the butyl derivative 32 ([H-3]PENT K-i = 0.51 nM; [H-3]DTG K-i = 0.69 nM) as novel high-affinity sigma-selective agents. An ethylene spacer was optimum with para-substituted analogs. A notable finding was the discovery of 2-(4-phenylpiperidinyl) ethyl 1-(4-nitrophenyl)cyclopentanecarboxylate hydrochloride (15) (RLH-033), which demonstrated potent affinity for the [H-3]PENT-defined sigma site with a K-i of 50 pM, selectivity for sigma(1) over muscarinic M(1) (> 17600-fold), M(2) (> 34200-fold), dopamine D-1 (> 58000-fold), and D-2 (> 7000-fold) receptors, and inactivity at phencyclidine, NMDA, and opioid receptors. RLH-033 is a valuable tool which will aid further in understanding the biology of the sigma recognition site. Information from this research has further defined the topography of the sigma recognition site, which may provide an explanation for the diverse structures which bind with relatively high affinity.
• Hudkins Robert L., Mailman Richard B., DeHaven-Hudkins Diane L., J. Med. Chem, 37 (1994) N 13, S 1964- 1970
  作者：Hudkins Robert L., Mailman Richard B., DeHaven-Hudkins Diane L.

  DOI：——

  日期：——