(3-carboxy-propyl)triphenylphosphonium chloride | 60633-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-carboxy-propyl)triphenylphosphonium chloride
• 英文别名: 4-Triphenylphosphaniumylbutanoate;hydrochloride
• CAS: 60633-18-3
• 化学式: C₂₂H₂₂O₂P*Cl
• 分子量: 384.842
• InChiKey: KWZQORSVCNLHBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-carboxy-propyl)triphenylphosphonium chloride 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 24.17h， 生成 (5-羧基戊基)三苯基溴化磷
  参考文献：
  名称：

  Novel synthesis of .omega.-(diphenylphosphinyl)alkylcarboxylic acids from triphenyl-.omega.-carboxyalkylphosphonium salts

  摘要：

  DOI：

  10.1021/jo01299a040
• 作为产物：
  描述：

  4-氯丙酸 、 三苯基膦 以 甲苯 为溶剂， 反应 3.0h， 以78%的产率得到(3-carboxy-propyl)triphenylphosphonium chloride
  参考文献：
  名称：

  与靶向线粒体ATP敏感钾通道的二氮嗪有关的1,2,4-苯并噻二嗪1,1-二氧化物的三苯基phosph盐

  摘要：

  本工作旨在确定能够靶向线粒体ATP敏感性钾通道（mitoK ATP通道）的新型离子通道调节剂。一种创新方法应包括将阳离子和疏水性三苯基phosph片段固定在已知的K ATP通道开放剂的结构上。预期此类phospho盐穿过生物膜并积聚到线粒体中。 先前的工作表明，在大多数情况下，在4 H -1,2,4-苯并噻二嗪1,1-二氧化物K ATP通道开放剂的3位上存在（R）-1-羟基-2-丙基氨基链，对胰腺型（SUR1 / Kir6.2）K ATP通道的选择性。为了靶向心脏mitoK ATP通道，我们决定通过SUR1选择性（R）-7-氯-3-（1-羟基-2-丙基）氨基-4 H -1上的酯键引入三苯基phosph基团，2,4-苯并噻二嗪1,1-二氧化物。发现新化合物保留了对胰岛素分泌的抑制活性（SUR1型K ATP通道开放剂），但没有观察到明显的证据表明心肌细胞对线粒体有影响（氧气消耗量，呼吸参数和H

  DOI：

  10.1016/j.bmcl.2013.08.091

文献信息

• Pyridine compounds which are useful in treating a disease state
  申请人：Hoffman-La Roche Inc.

  公开号：US04927838A1

  公开（公告）日：1990-05-22

  The invention relates to compounds of the formula ##STR1## wherein Y and Y' are hydrogen or taken together are O or S, *A is paraphenylene or *----(CH.sub.2).sub.n --(X).sub.s --(CH.sub.2).sub.r ----, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, m is an integer from 0 to 1, s is an integer from 0 to 1, provided that when s is 1, n+m must be at least 2, t is an integer from 0 to 10, R.sub.1 and R.sub.2, independently, are lower alkyl, lower alkenyl or aryl, or one of R.sub.1 or R.sub.2 is hydrogen and the other is ##STR2## wherein W is ##STR3## --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --, O, S, or ##STR4## and X.sub.1 is lower alkyl, phenyl unsubstituted or mono-, di- or trisubstituted by lower alkoxy, lower alkyl or halogen, and X.sub.2, X.sub.3 and X.sub.4, independently, are hydrogen, lower alkyl, lower alkoxy or halogen, R.sub.3 is hydrogen, lower alkyl or aryl, R.sub.4 is hydrogen, lower alkyl, aryl, aryl-lower alkyl or acyl, R.sub.5 is hydrogen or lower alkyl, R.sub.6 is hydrogen, lower alkyl, cycloalkyl, Het-lower alkyl or aryl, Het is a monocyclic 6-membered heteroaromatic radical containing one or two nitrogen atoms, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment, and when R.sub.5 and R.sub.6 are different, their enantiomers and racemic mixtures thereof, when R.sub.1 and R.sub.2 are different, their geometric isomers, and pharmaceutically acceptable acid addition salts thereof.

  该发明涉及以下式的化合物##STR1##其中Y和Y'是氢或一起取O或S，*A是对苯二甲基或*----(CH.sub.2).sub.n --(X).sub.s --(CH.sub.2).sub.r ----，X是O、S或--CH.dbd.CH--，n或r独立地是0到3的整数，m是0到1的整数，s是0到1的整数，但当s为1时，n+m必须至少为2，t是0到10的整数，R.sub.1和R.sub.2独立地是较低的烷基、较低的烯烃基或芳基，或者R.sub.1或R.sub.2中的一个是氢，另一个是##STR2##其中W是##STR3##--CH.sub.2 --CH.sub.2 --，--CH.sub.2 --，O，S，或##STR4##，X.sub.1是较低的烷基，苯基未取代或被较低的烷氧基、较低的烷基或卤素单取代、双取代或三取代，X.sub.2、X.sub.3和X.sub.4独立地是氢、较低的烷基、较低的烷氧基或卤素，R.sub.3是氢、较低的烷基或芳基，R.sub.4是氢、较低的烷基、芳基、芳基-较低的烷基或酰基，R.sub.5是氢或较低的烷基，R.sub.6是氢、较低的烷基、环烷基、Het-较低的烷基或芳基，Het是含有一个或两个氮原子的单环6-成员杂芳基，该基团可以被较低的烷基、卤素或芳基取代，星号表示连接点，当R.sub.5和R.sub.6不同时，它们的对映异构体和外消旋混合物，当R.sub.1和R.sub.2不同时，它们的几何异构体，以及其药学上可接受的酸盐。
• HFIP Solvent Enables Alcohols To Act as Alkylating Agents in Stereoselective Heterocyclization
  作者：Yuxiang Zhu、Ignacio Colomer、Amber L. Thompson、Timothy J. Donohoe

  DOI：10.1021/jacs.9b02198

  日期：2019.4.24

  method for the stereoselective synthesis of highly functionalized oxygen heterocycles using allyl or benzyl alcohols as alkylating agents is presented. The process is efficient and atom economic, generating water as the only stoichiometric byproduct. Substoichiometric amounts of Ti(OiPr)4 in HFIP solvent are key to this reactivity, and the method tolerates a broad substitution pattern on both the alcohol

  提出了一种使用烯丙醇或苯甲醇作为烷化剂立体选择性合成高度官能化氧杂环的新方法。该过程高效且原子经济，产生的水是唯一的化学计量副产品。HFIP 溶剂中低于化学计量的 Ti(OiPr)4 是这种反应性的关键，并且该方法在醇引发剂和高烯丙醇底物上都可以容忍广泛的取代模式。初步的机理研究揭示了钛配合物与 HFIP 的原位形成，这可能会引发环化反应。产品的进一步立体选择性功能化允许获得各种有趣的杂环结构。
• Alkenecarboxylic acid compounds
  申请人：Adir et Compagnie

  公开号：US05436343A1

  公开（公告）日：1995-07-25

  Compounds of formula (I): ##STR1## in which: R.sub.1 and R.sub.2, which may be identical or different, represent a linear or branched (C.sub.1 C.sub.6) alkyl radical, a substituted or unsubstituted phenyl radical, a pyridyl radical or a thienyl radical, or, with the carbon atom to which they are attached, a substituted or unsubstituted (C.sub.4 -C.sub.7) cycloalkyl ring, R.sub.3 represents a substituted or unsubstituted phenylsulfonyl radical, a linear or branched (C.sub.1 -C.sub.6) alkyl radical, an alkylaminocarbonyl radical, or a linear or branched (C.sub.1 -C.sub.6) acyl radical, R.sub.4 represents any one of the radicals: --CH.dbd.CH--(CH.sub.2).sub.p --CO.sub.2 H or --CH.sub.2 --CH.sub.2 --(CH.sub.2)p--CO.sub.2 H in which p is equal to 0, 1, 2 or 3, n and m, which may be identical or different, represent 0, 1 or 2, their isomers, enantiomers, diastereoisomers and epimers as well as their addition salts with a pharmaceutically acceptable acid or base.

  式(I)的化合物：##STR1##其中：R.sub.1和R.sub.2，可以相同也可以不同，代表线性或支链(C.sub.1 -C.sub.6)烷基基团，取代或未取代的苯基基团，吡啶基团或噻吩基团，或者与它们连接的碳原子一起，取代或未取代的(C.sub.4 -C.sub.7)环烷基环，R.sub.3代表取代或未取代的苯基磺酰基团，线性或支链(C.sub.1 -C.sub.6)烷基基团，烷基氨基甲酰基团，或线性或支链(C.sub.1 -C.sub.6)酰基基团，R.sub.4代表以下任一基团：--CH.dbd.CH--(CH.sub.2).sub.p --CO.sub.2 H或--CH.sub.2 --CH.sub.2 --(CH.sub.2)p--CO.sub.2 H其中p等于0, 1, 2或3，n和m，可以相同也可以不同，代表0, 1或2，它们的异构体，对映体，非对映异构体和差向异构体，以及它们与药学上可接受的酸或碱形成的加合物。
• Synthesis and Thromboxane A2 Antagonistic Activity of ((1-Aryl(or Benzyl)-1-(benzenesulfonamido)methyl)phenyl)alkanoic Acid Derivatives.
  作者：Shuniciro SAKURAI、Nobuo OGAWA、Tomio SUZUKI、Ken-ichi KATO、Tetsuo OHASHI、Shingo YASUDA、Hideo KATO、Yasuo ITO

  DOI：10.1248/cpb.44.765

  日期：——

  In order to find new antiasthematic and antithrombotic agents, various [[1-aryl(or benzyl)-1-(benzenesulfonamido)methyl]phenyl]alkanoic acids derivatives were synthesized. Evaluation of these compounds for thromboxane A2 (TXA2) antagonistic activities indicated that 4-[4-[(4-chlorobenzenesulfonamido)phenylmethyl]phenyl]butyric acid (6h), 4-[4-[1-(4-chlorobenzenesulfonamido)-2-phenylethyl]butyric acid (6y) and many other compounds have potent inhibitory effects on U-46619-induced guinea-pig platelet aggregation. No significant difference in the inhibitory effect between (+)-6h and its antipode could be detected, although (+)-6y was about 10 times more potent than (-)-6y. The pKb values of 6h and 6y were estimated to be 8.9 and 10, respectively on U-46619-induced contraction of guinea-pig trachea as a pharmacological measure of TXA2 antagonistic activity. These compounds also showed potent inhibitory effects on U-46619-induced bronchoconstriction in guinea-pig after oral administration in vivo. They were also evaluated for other related pharmacological effects involving the arachidonic acid cascade. It ws found that these compounds possess TXA2 synthase inhibitory activity together with TXA2 antagonistic activity, and 6h also possesses weak leukotriene D4 (LTD4) antagonistic acitivity. Structure-activity relationships for TXA2 antagonistic activity of these derivatives are discussed.

  为了寻找新的抗静血和抗血栓药物，人们合成了各种[[1-芳基（或苄基）-1-（苯磺酰胺基）甲基]苯基]烷酸衍生物。对这些化合物的血栓素 A2（TXA2）拮抗活性评估表明，4-[4-[(4-氯苯磺酰胺基)苯基甲基]苯基]丁酸（6h）、4-[4-[1-(4-氯苯磺酰胺基)-2-苯基乙基]丁酸（6y）和许多其他化合物对 U-46619 诱导的豚鼠血小板聚集具有强效抑制作用。尽管(+)-6y 的抑制作用是(-)-6y 的 10 倍左右，但(+)-6h 与其反式之间的抑制作用并无明显差异。在 U-46619 诱导的豚鼠气管收缩中，作为 TXA2 拮抗活性的药理学指标，6h 和 6y 的 pKb 值分别为 8.9 和 10。这些化合物在体内口服后，对 U-46619 诱导的豚鼠支气管收缩也有很强的抑制作用。还对涉及花生四烯酸级联的其他相关药理作用进行了评估。结果发现，这些化合物具有 TXA2 合酶抑制活性和 TXA2 拮抗活性，6h 还具有微弱的白三烯 D4（LTD4）拮抗活性。本文讨论了这些衍生物 TXA2 拮抗活性的结构-活性关系。
• [EN] PYRROLIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] MODULATEURS DE PYRROLIDINE DE L'ACTIVITE DU RECEPTEUR DES CHIMIOKINES
  申请人：MERCK & CO INC

  公开号：WO2000059503A1

  公开（公告）日：2000-10-12

  The present invention is directed to pyrrolidine compounds of formula (I) (wherein R?1, R2, R3, R4, R5, R6¿ and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.

  本发明涉及式(I)的吡咯烷化合物（其中R1，R2，R3，R4，R5，R6和n的定义如下），它们可用作趋化因子受体活性调节剂。特别地，这些化合物可用作趋化因子受体CCR-5和/或CCR-3的调节剂。