4-(3,5-dimethylpyrazol-1-yl)phenyl iodide | 179421-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3,5-dimethylpyrazol-1-yl)phenyl iodide
• 英文别名: 1-(4-iodophenyl)-3,5-dimethylpyrazole
• CAS: 179421-17-1
• 化学式: C₁₁H₁₁IN₂
• 分子量: 298.126
• InChiKey: PIYNWAKVTXLSIM-UHFFFAOYSA-N

物化性质

• 沸点：
  334.7±30.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(3,5-dimethylpyrazol-1-yl)phenyl iodide 在 氢氧化钾 、 叔丁醇 作用下， 反应 4.0h， 生成 4-{3-[4-(3,5-Dimethyl-pyrazol-1-yl)-phenylsulfanyl]-phenyl}-tetrahydro-pyran-4-carboxylic acid amide
  参考文献：
  名称：

  5-Lipoxygenase inhibitors: convenient synthesis of 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide analogues

  摘要：

  A convenient synthetic route to 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-earboxamide analogues as 5-LO inhibitors is described. This methodology enabled rapid development of structure-activity relationships (SARs) leading to improvement of pharmacological properties. Thus, new compounds with higher 5-LO inhibitory potency were discovered. The stereo-chemistry requirements of the tetrahydropyran ring are also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.041
• 作为产物：
  描述：

  3,5-二甲基吡唑 、 对氟碘苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以61%的产率得到4-(3,5-dimethylpyrazol-1-yl)phenyl iodide
  参考文献：
  名称：

  5-Lipoxygenase inhibitors: convenient synthesis of 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide analogues

  摘要：

  A convenient synthetic route to 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-earboxamide analogues as 5-LO inhibitors is described. This methodology enabled rapid development of structure-activity relationships (SARs) leading to improvement of pharmacological properties. Thus, new compounds with higher 5-LO inhibitory potency were discovered. The stereo-chemistry requirements of the tetrahydropyran ring are also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.041

文献信息

• [EN] 5-LIPOXYGENASE INHIBITORS<br/>[FR] INHIBITEURS DE LA LIPOXYGENASE-5
  申请人：PFIZER INC.

  公开号：WO1996011911A1

  公开（公告）日：1996-04-25

  (EN) Novel compounds having the ability to inhibit 5-lipoxygenase enzyme and having formula (I) and the pharmaceutically acceptable salts thereof, wherein Ar1 is a heterocyclic moiety which is selected from imidazolyl, pyrrolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, indolyl, indazolyl and benzimidazolyl, which is bonded to X1 through a ring nitrogen atom, and which may be optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, C1-4 alkyl and the like; X1 is a direct bond or C1-4 alkylene; Ar2 is phenylene optionally substituted with halo, hydroxy, cyano, amino and the like; X2 is -A-X- or -X-A- wherein A is a direct bond or C1-4 alkylene and X is oxy, thio, sulfinyl or sulfonyl; Ar3 is phenylene, pyridylene, thienylene, furylene, oxazolylene or thiazolylene optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, C1-4 alkyl and the like; R1 and R2 are each C1-4 alkyl, or together they form a group of formula -D1-Z-D2- which together with the carbon atom to which it is attached defines a ring having 3 to 8 atoms, wherein D1 and D2 are C1-4 alkylene and Z is a direct bond or oxy, thio, sulfinyl, sulfonyl, or vinylene, and D1 and D2 may be substituted by C1-3 alkyl; and Y is CONR3R4, CN, C(R3)=N-OR4, COOR3, COR3 or CSNR3R4, wherein R3 and R4 are each H or C1-4 alkyl. These compounds are useful in the treatment or alleviation of inflammatory diseases, allergy and cardiovascular diseases in mammals and as the active ingredient in pharmaceutical compositions for treating such conditions.(FR) L'invention concerne des composés nouveaux capables d'inhiber l'enzyme lipoxygenase-5 et ayant la formule (I), ainsi que leurs sels pharmaceutiquement acceptables. Dans la formule, Ar1 est une fraction hétérocyclique sélectionnée parmi imidazolyle, pyrrolyle, pyrazolyle, 1,2,3-triazolyle, 1,2,4-triazolyle, indolyle, indazolyle et benzimidazolyle, liés à X1 par un atome cyclique d'azote et le cas échéant substitués par un ou deux substituants sélectionnés parmi halo, hydroxy, cyano, amino, alkyle C1-4 et similaires; X1 est une liaison directe ou alcylène C1-4; Ar2 désigne phénylène le cas échéant substitué par halo, hydroxy, cyano, amino et similaires; X2 désigne -A-X- ou -X-A-, où A désigne une liaison directe ou alcylène C1-4 et X désigne oxy, thio, sulfinyle ou sulfonyle; Ar3 désigne phénylène, pyridylène, thiénylène, furylène, oxyzolylène ou thiazolylène le cas échéant substitués par un ou deux substituants sélectionnés parmi halo, hydroxy, cyano, amino alkyle C1-4 et similaires; R1 et R2 désignent chacun alkyle C1-4, ou forment ensemble un groupe ayant la formule -D1-Z-D2- qui définit avec l'atome de carbone auquel il est lié un composé cyclique ayant 3 à 8 atomes et dans lequel D1 et D2 désignent alcylène C1-4 et Z désigne une liaison directe ou oxy, thio, sulfinyle, sulfonyle ou vinylène, et D1 et D2 peuvent être substitués par alkyle C1-3; et Y désigne CONR3R4, CN, C(R3)=N-OR4, COOR3, COR3 ou CSNR3R4, où R3 et R4 désignent tous les deux H ou alkyle C1-4. Ces composés sont utiles pour traiter ou soulager des maladies inflammatoires, des allergies et des maladies cardio-vasculaires chez des mammifères et comme principes actifs de compositions pharmaceutiques de traitement de ces maladies.

  这是一种具有抑制5-脂氧合酶酶活性的新型化合物，其化学式为（I）及其药学上可接受的盐。其中，Ar1是通过环氮原子与X1连接的杂环基团，可选用的杂环基团包括咪唑基、吡咯基、吡唑基、1,2,3-三唑基、1,2,4-三唑基、吲哚基、吲唑基和苯并咪唑基，可以选择地取代为卤素、羟基、氰基、氨基、C1-4烷基等一或两个取代基；X1是直接键或C1-4烷基；Ar2是苯基，可选用的取代基包括卤素、羟基、氰基、氨基等；X2是-A-X-或-X-A-，其中A是直接键或C1-4烷基，X是氧、硫、亚硫酰基或磺酰基；Ar3是苯基、吡啶基、噻吩基、呋喃基、噻唑基，可以选择地取代为卤素、羟基、氰基、氨基、C1-4烷基等一或两个取代基；R1和R2分别是C1-4烷基，或者它们一起形成一个公式为-D1-Z-D2-的基团，该基团与所连接的碳原子共同定义具有3-8个原子的环，其中D1和D2是C1-4烷基，Z是直接键、氧、硫、亚硫酰基、磺酰基或乙烯基，D1和D2可以被C1-3烷基取代；Y是CONR3R4、CN、C（R3）=N-OR4、COOR3、COR3或CSNR3R4，其中R3和R4分别是氢或C1-4烷基。这些化合物在哺乳动物的炎症性疾病、过敏和心血管疾病的治疗或缓解中有用，并可作为治疗这些疾病的药物组合物的活性成分。
• 5-lipoxygenase inhibitors
  申请人：Pfizer Inc

  公开号：US06063928A1

  公开（公告）日：2000-05-16

  Novel compounds having the ability to inhibit 5-lipoxygenase enzyme and having the following formula I: ##STR1## and the pharmaceutically acceptable salts thereof, wherein Ar.sup.1 is a heterocyclic moiety which is selected from imidazolyl, pyrrolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, indolyl, indazolyl and benzimidazolyl, which is bonded to X.sup.1 through a ring nitrogen atom, and which may be optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, C.sub.1-4 alkyl and the like; X.sup.1 is a direct bond or C.sub.1-4 alkylene; Ar.sup.2 is phenylene optionally substituted with halo, hydroxy, cyano, amino and the like; X.sup.2 is --A--X-- or --X--A-- wherein A is a direct bond or C.sub.1-4 alkylene and X is oxy, thio, sulfinyl or sulfonyl; Ar.sup.3 is phenylene, pyridylene, thienylene, furylene, oxazolylene or thiazolylene optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, C.sub.1-4 alkyl and the like; R.sup.1 and R.sup.2 are each C.sub.1-4 alkyl, or together they form a group of formula --D.sup.1 --Z--D.sup.2 -- which together with the carbon atom to which it is attached defines a ring having 3 to 8 atoms, wherein D.sup.1 and D.sup.2 are C.sub.1-4 alkylene and Z is a direct bond or oxy, thio, sulfinyl, sulfonyl, or vinylene, and D.sup.1 and D.sup.2 may be substituted by C.sub.1-3 alkyl; and Y is CONR.sup.3 R.sup.4, CN, C(R.sup.3).dbd.N--OR.sup.4, COOR.sup.3, COR.sup.3 or CSNR.sup.3 R.sup.4, wherein R.sup.3 and R.sup.4 are each H or C.sub.1-4 alkyl. These compounds are useful in the treatment or alleviation of inflammatory diseases, allergy and cardiovascular diseases in mammals and as the active ingredient in pharmaceutical compositions for treating such conditions.

  具有抑制5-脂氧合酶酶活性的新型化合物，其具有以下结构式I：##STR1##及其药学上可接受的盐，其中Ar.sup.1是从咪唑基，吡咯基，吡唑基，1,2,3-三唑基，1,2,4-三唑基，吲哚基，吲唑基和苯并咪唑基中选择的杂环基，其通过环氮原子与X.sup.1连接，并且可以选择性地用一个或两个卤素、羟基、氰基、氨基、C.sub.1-4烷基等取代；X.sup.1是直接键或C.sub.1-4烷基；Ar.sup.2是苯基，可选地用卤素、羟基、氰基、氨基等取代；X.sup.2是--A--X--或--X--A--，其中A是直接键或C.sub.1-4烷基，X是氧、硫、亚硫酰基或磺酰基；Ar.sup.3是苯基，吡啶基，噻吩基，呋喃基，噁唑基或噻唑基，可选地用一个或两个卤素、羟基、氰基、氨基、C.sub.1-4烷基等取代；R.sup.1和R.sup.2分别是C.sub.1-4烷基，或者它们一起形成一个公式为--D.sup.1--Z--D.sup.2--的基团，与其连接的碳原子定义有3到8个原子的环，其中D.sup.1和D.sup.2是C.sub.1-4烷基，Z是直接键或氧、硫、亚硫酰基、磺酰基或乙烯基，D.sup.1和D.sup.2可以被C.sub.1-3烷基取代；Y是CONR.sup.3R.sup.4，CN，C(R.sup.3).dbd.N--OR.sup.4，COOR.sup.3，COR.sup.3或CSNR.sup.3R.sup.4，其中R.sup.3和R.sup.4分别是H或C.sub.1-4烷基。这些化合物在哺乳动物中治疗或缓解炎症性疾病、过敏和心血管疾病，并作为治疗这些疾病的药物组成部分。
• Compounds and compositions for inducing chondrogenesis
  申请人：NOVARTIS AG

  公开号：US10188638B2

  公开（公告）日：2019-01-29

  The present invention provides compounds of formula I: or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof, wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds, and methods of using such compounds for treatment of joint damage or joint injury in a mammal, and for inducing differentiation of mesenchymal stem cells into chondrocytes.

  本发明提供了式 I 的化合物： 或其药学上可接受的盐、同系物或立体异构体，其中变量如本文所定义。本发明进一步提供了包含此类化合物的药物组合物，以及使用此类化合物治疗哺乳动物关节损伤或关节损伤和诱导间充质干细胞分化为软骨细胞的方法。
• Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl2 and NH4SCN/KSeCN
  作者：Jialiang Wu、Haofeng Shi、Xuemin Li、Jiaxin He、Chen Zhang、Fengxia Sun、Yunfei Du

  DOI：10.3762/bjoc.20.128

  日期：——

  Abstract A series of 4-thio/seleno-cyanated pyrazoles was conveniently synthesized from 4-unsubstituted pyrazoles using NH4SCN/KSeCN as thio/selenocyanogen sources and PhICl2 as the hypervalent iodine oxidant. This metal-free approach was postulated to involve the in situ generation of reactive thio/selenocyanogen chloride (Cl–SCN/SeCN) from the reaction of PhICl2 and NH4SCN/KSeCN, followed by an electrophilic

  抽象的 以NH 4 SCN/KSeCN为硫代/硒氰源，PhICl 2为高价碘氧化剂，以4-未取代吡唑为原料，方便地合成了一系列4-硫代/硒氰化吡唑。这种无金属方法被认为涉及通过 PhICl 2和 NH 4 SCN/KSeCN 的反应原位生成活性硫代/硒氰氯化物 (Cl–SCN/SeCN)，然后对吡唑骨架进行亲电硫代/硒氰化。 Beilstein J. Org. Chem. 2024, 20, 1453–1461. doi:10.3762/bjoc.20.128
• 5-LIPOXYGENASE INHIBITORS
  申请人：PFIZER INC.

  公开号：EP0787127A1

  公开（公告）日：1997-08-06